Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Southwest Airlines
Cheapest Month June
Cheapest Day of the Week Tuesday
Cheapest Airline Southwest Airlines

The cheapest airline(s) flying from Chicago to Boston is Southwest Airlines.

  • Southwest Airlines Southwest Airlines
  • JetBlue Airways JetBlue Airways
  • American Airlines American Airlines
  • United Airlines United Airlines
  • Spirit Airlines Spirit Airlines
  • Frontier Airlines Frontier Airlines
  • Allegiant Air LLC Allegiant Air LLC
  • Sun Country Airlines Sun Country Airlines
  • Alaska Airlines Alaska Airlines
  • Hawaiian Airlines Hawaiian Airlines
Cheapest Month June

Travel Period: June 2025 - May 2026

The cheapest month(s) to fly from Chicago to Boston is June.

  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
  • Feb 2026
  • Mar 2026
  • Apr 2026
  • May 2026
Cheapest Day of the Week Tuesday

The cheapest day(s) of the week to fly from Chicago to Boston is Tuesday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Fri, 2 May, 2025

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    All
    • Airline Filter by Airline
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      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 19:20 MDW
        22:35 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 19:20 - BOS 22:35 2h 15m Direct
      • MDWChicago Midway Airport 19:20
      • BOSBoston Logan International Airport 22:35
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 1132)Boeing 737 800
      • Southwest Airlines (WN 1132)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 19:31 ORD
        23:00 BOS
        2Hrs, 29m Direct
      • ORDChicago O'Hare International Airport 19:31 - BOS 23:00 2h 29m Direct
      • ORDChicago O'Hare International Airport 19:31
      • BOSBoston Logan International Airport 23:00
      • 2h 29m
      • Direct
      • JetBlue Airways (B6 1012)Airbus A220 300
      • JetBlue Airways (B6 1012)
        • M
        • -
        • W
        • T
        • F
        • -
        • S
      • Airbus A220 300
      • 19:31 ORD
        23:00 BOS
        2Hrs, 29m Direct
      • ORDChicago O'Hare International Airport 19:31 - BOS 23:00 2h 29m Direct
      • ORDChicago O'Hare International Airport 19:31
      • BOSBoston Logan International Airport 23:00
      • 2h 29m
      • Direct
      • JetBlue Airways (B6 1012)Airbus
      • JetBlue Airways (B6 1012)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Airbus
      • 20:20 ORD
        23:44 BOS
        2Hrs, 24m Direct
      • ORDChicago O'Hare International Airport 20:20 - BOS 23:44 2h 24m Direct
      • ORDChicago O'Hare International Airport 20:20
      • BOSBoston Logan International Airport 23:44
      • 2h 24m
      • Direct
      • American Airlines (AA 4796)Embraer Emb 175
      • American Airlines (AA 4796)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Embraer Emb 175
      • 20:40 MDW
        23:55 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 20:40 - BOS 23:55 2h 15m Direct
      • MDWChicago Midway Airport 20:40
      • BOSBoston Logan International Airport 23:55
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 676)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 676)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 21:20 ORD
        00:45 BOS
        2Hrs, 25m Direct
      • ORDChicago O'Hare International Airport 21:20 - BOS 00:45 2h 25m Direct
      • ORDChicago O'Hare International Airport 21:20
      • BOSBoston Logan International Airport 00:45
      • 2h 25m
      • Direct
      • United Airlines (UA 1237)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1237)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 Max 9 Passenger
      • 21:20 ORD
        00:45 BOS
        2Hrs, 25m Direct
      • ORDChicago O'Hare International Airport 21:20 - BOS 00:45 2h 25m Direct
      • ORDChicago O'Hare International Airport 21:20
      • BOSBoston Logan International Airport 00:45
      • 2h 25m
      • Direct
      • United Airlines (UA 1237)Boeing 737 800
      • United Airlines (UA 1237)
        • M
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 05:30 MDW
        08:45 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 05:30 - BOS 08:45 2h 15m Direct
      • MDWChicago Midway Airport 05:30
      • BOSBoston Logan International Airport 08:45
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 404)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 404)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 06:50 MDW
        10:05 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 06:50 - BOS 10:05 2h 15m Direct
      • MDWChicago Midway Airport 06:50
      • BOSBoston Logan International Airport 10:05
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 1915)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1915)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 07:10 ORD
        10:38 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 07:10 - BOS 10:38 2h 28m Direct
      • ORDChicago O'Hare International Airport 07:10
      • BOSBoston Logan International Airport 10:38
      • 2h 28m
      • Direct
      • United Airlines (UA 2067)Boeing 737 900
      • United Airlines (UA 2067)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • Boeing 737 900
      • 07:10 ORD
        10:38 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 07:10 - BOS 10:38 2h 28m Direct
      • ORDChicago O'Hare International Airport 07:10
      • BOSBoston Logan International Airport 10:38
      • 2h 28m
      • Direct
      • United Airlines (UA 2067)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2067)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Boeing 737 Max 8 Passenger
      • 07:37 ORD
        11:12 BOS
        2Hrs, 35m Direct
      • ORDChicago O'Hare International Airport 07:37 - BOS 11:12 2h 35m Direct
      • ORDChicago O'Hare International Airport 07:37
      • BOSBoston Logan International Airport 11:12
      • 2h 35m
      • Direct
      • American Airlines (AA 3821)Embraer Emb 175
      • American Airlines (AA 3821)
        • M
        • T
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        • T
        • F
        • S
        • S
      • Embraer Emb 175
      • 07:50 MDW
        11:05 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 07:50 - BOS 11:05 2h 15m Direct
      • MDWChicago Midway Airport 07:50
      • BOSBoston Logan International Airport 11:05
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 404)Boeing 737 800
      • Southwest Airlines (WN 404)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 08:21 ORD
        11:43 BOS
        2Hrs, 22m Direct
      • ORDChicago O'Hare International Airport 08:21 - BOS 11:43 2h 22m Direct
      • ORDChicago O'Hare International Airport 08:21
      • BOSBoston Logan International Airport 11:43
      • 2h 22m
      • Direct
      • American Airlines (AA 547)Boeing 737 800
      • American Airlines (AA 547)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 08:45 ORD
        12:13 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 08:45 - BOS 12:13 2h 28m Direct
      • ORDChicago O'Hare International Airport 08:45
      • BOSBoston Logan International Airport 12:13
      • 2h 28m
      • Direct
      • JetBlue Airways (B6 312)Airbus A220 300
      • JetBlue Airways (B6 312)
        • M
        • T
        • -
        • T
        • F
        • -
        • S
      • Airbus A220 300
      • 09:20 ORD
        12:48 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 09:20 - BOS 12:48 2h 28m Direct
      • ORDChicago O'Hare International Airport 09:20
      • BOSBoston Logan International Airport 12:48
      • 2h 28m
      • Direct
      • United Airlines (UA 721)Boeing 737 Max 9 Passenger
      • United Airlines (UA 721)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 Max 9 Passenger
      • 10:10 MDW
        13:30 BOS
        2Hrs, 20m Direct
      • MDWChicago Midway Airport 10:10 - BOS 13:30 2h 20m Direct
      • MDWChicago Midway Airport 10:10
      • BOSBoston Logan International Airport 13:30
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 1915)Boeing 737 700
      • Southwest Airlines (WN 1915)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 10:20 MDW
        13:40 BOS
        2Hrs, 20m Direct
      • MDWChicago Midway Airport 10:20 - BOS 13:40 2h 20m Direct
      • MDWChicago Midway Airport 10:20
      • BOSBoston Logan International Airport 13:40
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 1240)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1240)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 10:35 ORD
        14:03 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 10:35 - BOS 14:03 2h 28m Direct
      • ORDChicago O'Hare International Airport 10:35
      • BOSBoston Logan International Airport 14:03
      • 2h 28m
      • Direct
      • United Airlines (UA 399)Airbus
      • United Airlines (UA 399)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Airbus
      • 10:35 ORD
        14:03 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 10:35 - BOS 14:03 2h 28m Direct
      • ORDChicago O'Hare International Airport 10:35
      • BOSBoston Logan International Airport 14:03
      • 2h 28m
      • Direct
      • United Airlines (UA 399)Boeing 737 800
      • United Airlines (UA 399)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 10:50 ORD
        14:18 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 10:50 - BOS 14:18 2h 28m Direct
      • ORDChicago O'Hare International Airport 10:50
      • BOSBoston Logan International Airport 14:18
      • 2h 28m
      • Direct
      • JetBlue Airways (B6 312)Embraer Emb E90
      • JetBlue Airways (B6 312)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer Emb E90
      • 10:50 ORD
        14:18 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 10:50 - BOS 14:18 2h 28m Direct
      • ORDChicago O'Hare International Airport 10:50
      • BOSBoston Logan International Airport 14:18
      • 2h 28m
      • Direct
      • JetBlue Airways (B6 312)Airbus A220 300
      • JetBlue Airways (B6 312)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Airbus A220 300
      • 11:49 ORD
        15:10 BOS
        2Hrs, 21m Direct
      • ORDChicago O'Hare International Airport 11:49 - BOS 15:10 2h 21m Direct
      • ORDChicago O'Hare International Airport 11:49
      • BOSBoston Logan International Airport 15:10
      • 2h 21m
      • Direct
      • American Airlines (AA 630)Airbus
      • American Airlines (AA 630)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Airbus
      • 11:50 ORD
        15:22 BOS
        2Hrs, 32m Direct
      • ORDChicago O'Hare International Airport 11:50 - BOS 15:22 2h 32m Direct
      • ORDChicago O'Hare International Airport 11:50
      • BOSBoston Logan International Airport 15:22
      • 2h 32m
      • Direct
      • American Airlines (AA 4394)Embraer Emb 175
      • American Airlines (AA 4394)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer Emb 175
      • 12:10 MDW
        15:30 BOS
        2Hrs, 20m Direct
      • MDWChicago Midway Airport 12:10 - BOS 15:30 2h 20m Direct
      • MDWChicago Midway Airport 12:10
      • BOSBoston Logan International Airport 15:30
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 1240)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1240)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 12:30 MDW
        15:50 BOS
        2Hrs, 20m Direct
      • MDWChicago Midway Airport 12:30 - BOS 15:50 2h 20m Direct
      • MDWChicago Midway Airport 12:30
      • BOSBoston Logan International Airport 15:50
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 1240)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1240)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 12:50 ORD
        16:17 BOS
        2Hrs, 27m Direct
      • ORDChicago O'Hare International Airport 12:50 - BOS 16:17 2h 27m Direct
      • ORDChicago O'Hare International Airport 12:50
      • BOSBoston Logan International Airport 16:17
      • 2h 27m
      • Direct
      • United Airlines (UA 1532)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1532)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 Max 8 Passenger
      • 13:15 MDW
        16:35 BOS
        2Hrs, 20m Direct
      • MDWChicago Midway Airport 13:15 - BOS 16:35 2h 20m Direct
      • MDWChicago Midway Airport 13:15
      • BOSBoston Logan International Airport 16:35
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 1240)Boeing 737 800
      • Southwest Airlines (WN 1240)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 13:22 ORD
        16:48 BOS
        2Hrs, 26m Direct
      • ORDChicago O'Hare International Airport 13:22 - BOS 16:48 2h 26m Direct
      • ORDChicago O'Hare International Airport 13:22
      • BOSBoston Logan International Airport 16:48
      • 2h 26m
      • Direct
      • American Airlines (AA 2837)Boeing 737 800
      • American Airlines (AA 2837)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 13:55 ORD
        17:23 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 13:55 - BOS 17:23 2h 28m Direct
      • ORDChicago O'Hare International Airport 13:55
      • BOSBoston Logan International Airport 17:23
      • 2h 28m
      • Direct
      • United Airlines (UA 580)Boeing 737 800
      • United Airlines (UA 580)
        • -
        • -
        • W
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 13:55 ORD
        17:19 BOS
        2Hrs, 24m Direct
      • ORDChicago O'Hare International Airport 13:55 - BOS 17:19 2h 24m Direct
      • ORDChicago O'Hare International Airport 13:55
      • BOSBoston Logan International Airport 17:19
      • 2h 24m
      • Direct
      • United Airlines (UA 580)Boeing 737 Max 9 Passenger
      • United Airlines (UA 580)
        • M
        • T
        • -
        • T
        • F
        • S
        • -
      • Boeing 737 Max 9 Passenger
      • 15:00 MDW
        18:20 BOS
        2Hrs, 20m Direct
      • MDWChicago Midway Airport 15:00 - BOS 18:20 2h 20m Direct
      • MDWChicago Midway Airport 15:00
      • BOSBoston Logan International Airport 18:20
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 3273)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3273)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 15:20 ORD
        18:43 BOS
        2Hrs, 23m Direct
      • ORDChicago O'Hare International Airport 15:20 - BOS 18:43 2h 23m Direct
      • ORDChicago O'Hare International Airport 15:20
      • BOSBoston Logan International Airport 18:43
      • 2h 23m
      • Direct
      • American Airlines (AA 3160)Airbus
      • American Airlines (AA 3160)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus
      • 16:15 MDW
        19:35 BOS
        2Hrs, 20m Direct
      • MDWChicago Midway Airport 16:15 - BOS 19:35 2h 20m Direct
      • MDWChicago Midway Airport 16:15
      • BOSBoston Logan International Airport 19:35
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 3273)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3273)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 16:20 ORD
        19:48 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 16:20 - BOS 19:48 2h 28m Direct
      • ORDChicago O'Hare International Airport 16:20
      • BOSBoston Logan International Airport 19:48
      • 2h 28m
      • Direct
      • United Airlines (UA 1677)Boeing 737 800
      • United Airlines (UA 1677)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 16:40 ORD
        20:01 BOS
        2Hrs, 21m Direct
      • ORDChicago O'Hare International Airport 16:40 - BOS 20:01 2h 21m Direct
      • ORDChicago O'Hare International Airport 16:40
      • BOSBoston Logan International Airport 20:01
      • 2h 21m
      • Direct
      • American Airlines (AA 3010)Boeing 737 800
      • American Airlines (AA 3010)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 17:05 ORD
        20:33 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 17:05 - BOS 20:33 2h 28m Direct
      • ORDChicago O'Hare International Airport 17:05
      • BOSBoston Logan International Airport 20:33
      • 2h 28m
      • Direct
      • American Airlines (AA 4373)Embraer Emb 175
      • American Airlines (AA 4373)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer Emb 175
      • 18:25 ORD
        21:57 BOS
        2Hrs, 32m Direct
      • ORDChicago O'Hare International Airport 18:25 - BOS 21:57 2h 32m Direct
      • ORDChicago O'Hare International Airport 18:25
      • BOSBoston Logan International Airport 21:57
      • 2h 32m
      • Direct
      • United Airlines (UA 1989)Airbus A321 Neo
      • United Airlines (UA 1989)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus A321 Neo
      • 18:25 MDW
        21:45 BOS
        2Hrs, 20m Direct
      • MDWChicago Midway Airport 18:25 - BOS 21:45 2h 20m Direct
      • MDWChicago Midway Airport 18:25
      • BOSBoston Logan International Airport 21:45
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 3273)Boeing 737 800
      • Southwest Airlines (WN 3273)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 18:30 MDW
        21:45 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 18:30 - BOS 21:45 2h 15m Direct
      • MDWChicago Midway Airport 18:30
      • BOSBoston Logan International Airport 21:45
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 1132)Boeing 737 800
      • Southwest Airlines (WN 1132)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 18:35 ORD
        22:07 BOS
        2Hrs, 32m Direct
      • ORDChicago O'Hare International Airport 18:35 - BOS 22:07 2h 32m Direct
      • ORDChicago O'Hare International Airport 18:35
      • BOSBoston Logan International Airport 22:07
      • 2h 32m
      • Direct
      • American Airlines (AA 407)Boeing 737 800
      • American Airlines (AA 407)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 05:00 ORD
        11:06 BOS
        5Hrs, 06m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - BOS 11:06 5h 06m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 08:55
      • CLTCharlotte Airport 08:07
        BOSBoston Logan International Airport 11:06
      • 5h 06m (48m)
      • 1 Stop CLT · Charlotte 48m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 1413)Airbus
      • American Airlines (AA 2842)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 05:00 ORD
        11:09 BOS
        5Hrs, 09m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - BOS 11:09 5h 09m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 08:55
      • CLTCharlotte Airport 08:07
        BOSBoston Logan International Airport 11:09
      • 5h 09m (48m)
      • 1 Stop CLT · Charlotte 48m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 1413)Boeing 737 800
      • American Airlines (AA 2842)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:45 MDW
        12:25 BOS
        5Hrs, 40m 1 Stop (BWI)
      • MDWChicago Midway Airport 05:45 - BOS 12:25 5h 40m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 05:45
        BWIBaltimore Washington International Airport 10:55
      • BWIBaltimore Washington International Airport 08:30
        BOSBoston Logan International Airport 12:25
      • 5h 40m (2h 25m)
      • 1 Stop BWI · Baltimore 2h 25m
      • Southwest Airlines (WN 1547)Boeing 737 700
        Southwest Airlines (WN 2594)Boeing 737 800
      • Southwest Airlines (WN 1547)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 05:45 MDW
        12:00 BOS
        5Hrs, 15m 1 Stop (BWI)
      • MDWChicago Midway Airport 05:45 - BOS 12:00 5h 15m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 05:45
        BWIBaltimore Washington International Airport 10:30
      • BWIBaltimore Washington International Airport 08:30
        BOSBoston Logan International Airport 12:00
      • 5h 15m (2h)
      • 1 Stop BWI · Baltimore 2h
      • Southwest Airlines (WN 3459)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2594)Boeing 737 800
      • Southwest Airlines (WN 3459)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 ORD
        12:03 BOS
        5Hrs, 03m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:03 5h 03m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:00
        DCAWashington Ronald Reagan National Airport 10:05
      • DCAWashington Ronald Reagan National Airport 08:54
        BOSBoston Logan International Airport 12:03
      • 5h 03m (1h 11m)
      • 1 Stop DCA · Washington 1h 11m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 4809)Embraer Emb 175
      • American Airlines (AA 523)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 ORD
        12:55 BOS
        5Hrs, 55m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:55 5h 55m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 06:00
        EWRNewark Liberty International Airport 11:35
      • EWRNewark Liberty International Airport 09:14
        BOSBoston Logan International Airport 12:55
      • 5h 55m (2h 21m)
      • 1 Stop EWR · New York City 2h 21m
      • United Airlines (UA 2693)Boeing 757 200 Series
        United Airlines (UA 1864)Boeing 737 700
      • United Airlines (UA 2693)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:00 ORD
        11:09 BOS
        4Hrs, 09m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:00 - BOS 11:09 4h 09m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:00
        DCAWashington Ronald Reagan National Airport 09:30
      • DCAWashington Ronald Reagan National Airport 08:54
        BOSBoston Logan International Airport 11:09
      • 4h 09m (36m)
      • 1 Stop DCA · Washington 36m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 4699)Embraer Emb 175
      • American Airlines (AA 523)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:00 ORD
        12:58 BOS
        5Hrs, 58m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:58 5h 58m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 06:00
        EWRNewark Liberty International Airport 11:38
      • EWRNewark Liberty International Airport 09:14
        BOSBoston Logan International Airport 12:58
      • 5h 58m (2h 24m)
      • 1 Stop EWR · New York City 2h 24m
      • United Airlines (UA 2693)Boeing 757 200 Series
        United Airlines (UA 1864)Airbus
      • United Airlines (UA 2693)
        • -
        • T
        • W
        • T
        • -
        • -
        • S
      • 06:00 ORD
        12:58 BOS
        5Hrs, 58m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:58 5h 58m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 06:00
        EWRNewark Liberty International Airport 11:35
      • EWRNewark Liberty International Airport 09:14
        BOSBoston Logan International Airport 12:58
      • 5h 58m (2h 21m)
      • 1 Stop EWR · New York City 2h 21m
      • United Airlines (UA 2693)Boeing 757 200 Series
        United Airlines (UA 3670)Embraer 170
      • United Airlines (UA 2693)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 ORD
        11:24 BOS
        4Hrs, 24m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:00 - BOS 11:24 4h 24m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:00
        DCAWashington Ronald Reagan National Airport 09:45
      • DCAWashington Ronald Reagan National Airport 08:54
        BOSBoston Logan International Airport 11:24
      • 4h 24m (51m)
      • 1 Stop DCA · Washington 51m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 4699)Embraer Emb 175
      • American Airlines (AA 523)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 06:00 ORD
        12:35 BOS
        5Hrs, 35m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:35 5h 35m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:00
        DCAWashington Ronald Reagan National Airport 10:55
      • DCAWashington Ronald Reagan National Airport 08:54
        BOSBoston Logan International Airport 12:35
      • 5h 35m (2h 01m)
      • 1 Stop DCA · Washington 2h 01m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 4809)Embraer Emb 175
      • American Airlines (AA 523)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 06:00 ORD
        12:58 BOS
        5Hrs, 58m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:58 5h 58m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 06:00
        EWRNewark Liberty International Airport 11:38
      • EWRNewark Liberty International Airport 09:14
        BOSBoston Logan International Airport 12:58
      • 5h 58m (2h 24m)
      • 1 Stop EWR · New York City 2h 24m
      • United Airlines (UA 2693)Boeing 737 900
        United Airlines (UA 1864)Airbus
      • United Airlines (UA 2693)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:10 ORD
        11:42 BOS
        4Hrs, 32m 1 Stop (JFK)
      • ORDChicago O'Hare International Airport 06:10 - BOS 11:42 4h 32m 1 Stop (JFK) New York City
      • ORDChicago O'Hare International Airport 06:10
        JFKNew York John F. Kennedy International Airport 10:30
      • JFKNew York John F. Kennedy International Airport 09:28
        BOSBoston Logan International Airport 11:42
      • 4h 32m (1h 02m)
      • 1 Stop JFK · New York City 1h 02m
      • JetBlue Airways (B6 406)Airbus A220 300
        JetBlue Airways (B6 418)Airbus
      • JetBlue Airways (B6 406)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:15 MDW
        12:35 BOS
        5Hrs, 20m 1 Stop (STL)
      • MDWChicago Midway Airport 06:15 - BOS 12:35 5h 20m 1 Stop (STL) Saint Louis
      • MDWChicago Midway Airport 06:15
        STLSt Louis Lambert Intl Airport 09:00
      • STLSt Louis Lambert Intl Airport 07:25
        BOSBoston Logan International Airport 12:35
      • 5h 20m (1h 35m)
      • 1 Stop STL · Saint Louis 1h 35m
      • Southwest Airlines (WN 1045)Boeing 737 800
        Southwest Airlines (WN 993)Boeing 737 700
      • Southwest Airlines (WN 1045)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:15 ORD
        11:42 BOS
        4Hrs, 27m 1 Stop (JFK)
      • ORDChicago O'Hare International Airport 06:15 - BOS 11:42 4h 27m 1 Stop (JFK) New York City
      • ORDChicago O'Hare International Airport 06:15
        JFKNew York John F. Kennedy International Airport 10:30
      • JFKNew York John F. Kennedy International Airport 09:30
        BOSBoston Logan International Airport 11:42
      • 4h 27m (1h)
      • 1 Stop JFK · New York City 1h
      • JetBlue Airways (B6 406)Airbus A220 300
        JetBlue Airways (B6 418)Airbus
      • JetBlue Airways (B6 406)
        • M
        • T
        • -
        • -
        • F
        • -
        • S
      • 06:15 ORD
        11:42 BOS
        4Hrs, 27m 1 Stop (JFK)
      • ORDChicago O'Hare International Airport 06:15 - BOS 11:42 4h 27m 1 Stop (JFK) New York City
      • ORDChicago O'Hare International Airport 06:15
        JFKNew York John F. Kennedy International Airport 10:30
      • JFKNew York John F. Kennedy International Airport 09:30
        BOSBoston Logan International Airport 11:42
      • 4h 27m (1h)
      • 1 Stop JFK · New York City 1h
      • JetBlue Airways (B6 406)Airbus A220 300
        JetBlue Airways (B6 418)Airbus A220 300
      • JetBlue Airways (B6 406)
        • -
        • -
        • W
        • T
        • -
        • -
        • -
      • 06:15 ORD
        13:11 BOS
        5Hrs, 56m 1 Stop (JFK)
      • ORDChicago O'Hare International Airport 06:15 - BOS 13:11 5h 56m 1 Stop (JFK) New York City
      • ORDChicago O'Hare International Airport 06:15
        JFKNew York John F. Kennedy International Airport 11:59
      • JFKNew York John F. Kennedy International Airport 09:30
        BOSBoston Logan International Airport 13:11
      • 5h 56m (2h 29m)
      • 1 Stop JFK · New York City 2h 29m
      • JetBlue Airways (B6 406)Airbus A220 300
        JetBlue Airways (B6 318)Airbus A220 300
      • JetBlue Airways (B6 406)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:17 ORD
        12:24 BOS
        5Hrs, 07m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 06:17 - BOS 12:24 5h 07m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 06:17
        LGANew York La Guardia Airport 11:12
      • LGANew York La Guardia Airport 09:23
        BOSBoston Logan International Airport 12:24
      • 5h 07m (1h 49m)
      • 1 Stop LGA · New York City 1h 49m
      • American Airlines (AA 327)Boeing 737 800
        American Airlines (AA 4650)Embraer Emb 175
      • American Airlines (AA 327)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 06:20 MDW
        12:45 BOS
        5Hrs, 25m 1 Stop (BWI)
      • MDWChicago Midway Airport 06:20 - BOS 12:45 5h 25m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 06:20
        BWIBaltimore Washington International Airport 11:15
      • BWIBaltimore Washington International Airport 09:05
        BOSBoston Logan International Airport 12:45
      • 5h 25m (2h 10m)
      • 1 Stop BWI · Baltimore 2h 10m
      • Southwest Airlines (WN 3299)Boeing 737 700
        Southwest Airlines (WN 2594)Boeing 737 800
      • Southwest Airlines (WN 3299)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:25 MDW
        11:50 BOS
        4Hrs, 25m 1 Stop (STL)
      • MDWChicago Midway Airport 06:25 - BOS 11:50 4h 25m 1 Stop (STL) Saint Louis
      • MDWChicago Midway Airport 06:25
        STLSt Louis Lambert Intl Airport 08:15
      • STLSt Louis Lambert Intl Airport 07:35
        BOSBoston Logan International Airport 11:50
      • 4h 25m (40m)
      • 1 Stop STL · Saint Louis 40m
      • Southwest Airlines (WN 461)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3139)Boeing 737 700
      • Southwest Airlines (WN 461)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:40 MDW
        11:55 BOS
        4Hrs, 15m 1 Stop (BWI)
      • MDWChicago Midway Airport 06:40 - BOS 11:55 4h 15m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 06:40
        BWIBaltimore Washington International Airport 10:25
      • BWIBaltimore Washington International Airport 09:30
        BOSBoston Logan International Airport 11:55
      • 4h 15m (55m)
      • 1 Stop BWI · Baltimore 55m
      • Southwest Airlines (WN 2357)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2594)Boeing 737 800
      • Southwest Airlines (WN 2357)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:50 MDW
        14:00 BOS
        6Hrs, 10m 1 Stop (BNA)
      • MDWChicago Midway Airport 06:50 - BOS 14:00 6h 10m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 06:50
        BNANashville Airport 10:25
      • BNANashville Airport 08:20
        BOSBoston Logan International Airport 14:00
      • 6h 10m (2h 05m)
      • 1 Stop BNA · Nashville 2h 05m
      • Southwest Airlines (WN 1904)Boeing 737 800
        Southwest Airlines (WN 3519)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1904)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:55 MDW
        13:40 BOS
        5Hrs, 45m 1 Stop (BNA)
      • MDWChicago Midway Airport 06:55 - BOS 13:40 5h 45m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 06:55
        BNANashville Airport 10:05
      • BNANashville Airport 08:25
        BOSBoston Logan International Airport 13:40
      • 5h 45m (1h 40m)
      • 1 Stop BNA · Nashville 1h 40m
      • Southwest Airlines (WN 256)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1860)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 256)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 07:00 ORD
        13:56 BOS
        5Hrs, 56m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 07:00 - BOS 13:56 5h 56m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 07:00
        PHLPhiladelphia International Airport 12:34
      • PHLPhiladelphia International Airport 10:04
        BOSBoston Logan International Airport 13:56
      • 5h 56m (2h 30m)
      • 1 Stop PHL · Philadelphia 2h 30m
      • American Airlines (AA 1854)Boeing 737 800
        American Airlines (AA 4481)Embraer Emb 175
      • American Airlines (AA 1854)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 07:00 ORD
        13:47 BOS
        5Hrs, 47m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - BOS 13:47 5h 47m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 11:20
      • CLTCharlotte Airport 10:05
        BOSBoston Logan International Airport 13:47
      • 5h 47m (1h 15m)
      • 1 Stop CLT · Charlotte 1h 15m
      • American Airlines (AA 1784)Boeing 737 800
        American Airlines (AA 885)Airbus
      • American Airlines (AA 1784)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 07:00 ORD
        13:53 BOS
        5Hrs, 53m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - BOS 13:53 5h 53m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 11:30
      • CLTCharlotte Airport 10:05
        BOSBoston Logan International Airport 13:53
      • 5h 53m (1h 25m)
      • 1 Stop CLT · Charlotte 1h 25m
      • American Airlines (AA 1784)Boeing 737 800
        American Airlines (AA 885)Airbus
      • American Airlines (AA 1784)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      • 07:00 ORD
        12:12 BOS
        4Hrs, 12m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 07:00 - BOS 12:12 4h 12m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 07:00
        PHLPhiladelphia International Airport 10:45
      • PHLPhiladelphia International Airport 10:04
        BOSBoston Logan International Airport 12:12
      • 4h 12m (41m)
      • 1 Stop PHL · Philadelphia 41m
      • American Airlines (AA 1854)Boeing 737 800
        American Airlines (AA 1416)Boeing 737 800
      • American Airlines (AA 1854)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 07:10 ORD
        12:58 BOS
        4Hrs, 48m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 07:10 - BOS 12:58 4h 48m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 07:10
        EWRNewark Liberty International Airport 11:35
      • EWRNewark Liberty International Airport 10:26
        BOSBoston Logan International Airport 12:58
      • 4h 48m (1h 09m)
      • 1 Stop EWR · New York City 1h 09m
      • United Airlines (UA 563)Boeing 757 200 Series
        United Airlines (UA 3670)Embraer 170
      • United Airlines (UA 563)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:10 ORD
        12:58 BOS
        4Hrs, 48m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 07:10 - BOS 12:58 4h 48m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 07:10
        EWRNewark Liberty International Airport 11:38
      • EWRNewark Liberty International Airport 10:26
        BOSBoston Logan International Airport 12:58
      • 4h 48m (1h 12m)
      • 1 Stop EWR · New York City 1h 12m
      • United Airlines (UA 563)Boeing 757 200 Series
        United Airlines (UA 1864)Airbus
      • United Airlines (UA 563)
        • M
        • T
        • W
        • T
        • -
        • -
        • S
      • 07:10 ORD
        12:55 BOS
        4Hrs, 45m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 07:10 - BOS 12:55 4h 45m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 07:10
        EWRNewark Liberty International Airport 11:35
      • EWRNewark Liberty International Airport 10:26
        BOSBoston Logan International Airport 12:55
      • 4h 45m (1h 09m)
      • 1 Stop EWR · New York City 1h 09m
      • United Airlines (UA 563)Boeing 757 200 Series
        United Airlines (UA 1864)Boeing 737 700
      • United Airlines (UA 563)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 07:19 ORD
        12:24 BOS
        4Hrs, 05m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 07:19 - BOS 12:24 4h 05m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 07:19
        LGANew York La Guardia Airport 11:12
      • LGANew York La Guardia Airport 10:28
        BOSBoston Logan International Airport 12:24
      • 4h 05m (44m)
      • 1 Stop LGA · New York City 44m
      • American Airlines (AA 2723)Boeing 737 800
        American Airlines (AA 4650)Embraer Emb 175
      • American Airlines (AA 2723)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 07:19 ORD
        14:15 BOS
        5Hrs, 56m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 07:19 - BOS 14:15 5h 56m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 07:19
        LGANew York La Guardia Airport 13:00
      • LGANew York La Guardia Airport 10:28
        BOSBoston Logan International Airport 14:15
      • 5h 56m (2h 32m)
      • 1 Stop LGA · New York City 2h 32m
      • American Airlines (AA 2723)Boeing 737 800
        American Airlines (AA 4769)Embraer 170
      • American Airlines (AA 2723)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 07:20 ORD
        14:15 BOS
        5Hrs, 55m 1 Stop (CMH)
      • ORDChicago O'Hare International Airport 07:20 - BOS 14:15 5h 55m 1 Stop (CMH) Columbus
      • ORDChicago O'Hare International Airport 07:20
        CMHColumbus Port Columbus Intl Airport 12:15
      • CMHColumbus Port Columbus Intl Airport 09:49
        BOSBoston Logan International Airport 14:15
      • 5h 55m (2h 26m)
      • 1 Stop CMH · Columbus 2h 26m
      • American Airlines (AA 3773)Embraer 170
        American Airlines (AA 4385)Embraer Emb 175
      • American Airlines (AA 3773)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:20 MDW
        12:25 BOS
        4Hrs, 05m 1 Stop (BWI)
      • MDWChicago Midway Airport 07:20 - BOS 12:25 4h 05m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 07:20
        BWIBaltimore Washington International Airport 10:55
      • BWIBaltimore Washington International Airport 10:05
        BOSBoston Logan International Airport 12:25
      • 4h 05m (50m)
      • 1 Stop BWI · Baltimore 50m
      • Southwest Airlines (WN 2357)Boeing 737 700
        Southwest Airlines (WN 2594)Boeing 737 800
      • Southwest Airlines (WN 2357)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 07:25 MDW
        14:30 BOS
        6Hrs, 05m 1 Stop (BWI)
      • MDWChicago Midway Airport 07:25 - BOS 14:30 6h 05m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 07:25
        BWIBaltimore Washington International Airport 13:00
      • BWIBaltimore Washington International Airport 10:10
        BOSBoston Logan International Airport 14:30
      • 6h 05m (2h 50m)
      • 1 Stop BWI · Baltimore 2h 50m
      • Southwest Airlines (WN 2357)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1902)Boeing 737 800
      • Southwest Airlines (WN 2357)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:30 MDW
        13:10 BOS
        4Hrs, 40m 1 Stop (BNA)
      • MDWChicago Midway Airport 07:30 - BOS 13:10 4h 40m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 07:30
        BNANashville Airport 09:40
      • BNANashville Airport 08:55
        BOSBoston Logan International Airport 13:10
      • 4h 40m (45m)
      • 1 Stop BNA · Nashville 45m
      • Southwest Airlines (WN 2741)Boeing 737 700
        Southwest Airlines (WN 1860)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2741)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 07:50 ORD
        14:54 BOS
        6Hrs, 04m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 07:50 - BOS 14:54 6h 04m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 07:50
        DCAWashington Ronald Reagan National Airport 13:15
      • DCAWashington Ronald Reagan National Airport 10:44
        BOSBoston Logan International Airport 14:54
      • 6h 04m (2h 31m)
      • 1 Stop DCA · Washington 2h 31m
      • American Airlines (AA 2345)Airbus
        American Airlines (AA 4493)Embraer Emb 175
      • American Airlines (AA 2345)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 08:03 ORD
        14:04 BOS
        5Hrs, 01m 1 Stop (SYR)
      • ORDChicago O'Hare International Airport 08:03 - BOS 14:04 5h 01m 1 Stop (SYR) Syracuse
      • ORDChicago O'Hare International Airport 08:03
        SYRSyracuse Airport 12:47
      • SYRSyracuse Airport 10:55
        BOSBoston Logan International Airport 14:04
      • 5h 01m (1h 52m)
      • 1 Stop SYR · Syracuse 1h 52m
      • American Airlines (AA 3651)Embraer 170
        American Airlines (AA 5873)Er4 Embraer Rj145 Amazon
      • American Airlines (AA 3651)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 08:05 ORD
        14:24 BOS
        5Hrs, 19m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 08:05 - BOS 14:24 5h 19m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 08:05
        DCAWashington Ronald Reagan National Airport 12:45
      • DCAWashington Ronald Reagan National Airport 11:00
        BOSBoston Logan International Airport 14:24
      • 5h 19m (1h 45m)
      • 1 Stop DCA · Washington 1h 45m
      • American Airlines (AA 2345)Airbus
        American Airlines (AA 4493)Embraer Emb 175
      • American Airlines (AA 2345)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:10 ORD
        14:15 BOS
        5Hrs, 05m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 08:10 - BOS 14:15 5h 05m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 08:10
        LGANew York La Guardia Airport 13:00
      • LGANew York La Guardia Airport 11:20
        BOSBoston Logan International Airport 14:15
      • 5h 05m (1h 40m)
      • 1 Stop LGA · New York City 1h 40m
      • American Airlines (AA 2079)Airbus
        American Airlines (AA 4769)Embraer 170
      • American Airlines (AA 2079)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 08:15 MDW
        14:30 BOS
        5Hrs, 15m 1 Stop (BWI)
      • MDWChicago Midway Airport 08:15 - BOS 14:30 5h 15m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 08:15
        BWIBaltimore Washington International Airport 13:00
      • BWIBaltimore Washington International Airport 11:05
        BOSBoston Logan International Airport 14:30
      • 5h 15m (1h 55m)
      • 1 Stop BWI · Baltimore 1h 55m
      • Southwest Airlines (WN 1547)Boeing 737 800
        Southwest Airlines (WN 1902)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1547)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 08:15 MDW
        14:00 BOS
        4Hrs, 45m 1 Stop (BNA)
      • MDWChicago Midway Airport 08:15 - BOS 14:00 4h 45m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 08:15
        BNANashville Airport 10:25
      • BNANashville Airport 09:45
        BOSBoston Logan International Airport 14:00
      • 4h 45m (40m)
      • 1 Stop BNA · Nashville 40m
      • Southwest Airlines (WN 367)Boeing 737 700
        Southwest Airlines (WN 3519)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 367)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 08:22 ORD
        13:56 BOS
        4Hrs, 34m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 08:22 - BOS 13:56 4h 34m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 08:22
        PHLPhiladelphia International Airport 12:34
      • PHLPhiladelphia International Airport 11:23
        BOSBoston Logan International Airport 13:56
      • 4h 34m (1h 11m)
      • 1 Stop PHL · Philadelphia 1h 11m
      • American Airlines (AA 471)Boeing 737 800
        American Airlines (AA 4481)Embraer Emb 175
      • American Airlines (AA 471)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      • 08:23 ORD
        13:56 BOS
        4Hrs, 33m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 08:23 - BOS 13:56 4h 33m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 08:23
        PHLPhiladelphia International Airport 12:34
      • PHLPhiladelphia International Airport 11:23
        BOSBoston Logan International Airport 13:56
      • 4h 33m (1h 11m)
      • 1 Stop PHL · Philadelphia 1h 11m
      • American Airlines (AA 471)Airbus
        American Airlines (AA 4481)Embraer Emb 175
      • American Airlines (AA 471)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 08:45 ORD
        15:54 BOS
        6Hrs, 09m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 08:45 - BOS 15:54 6h 09m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 08:45
        EWRNewark Liberty International Airport 14:35
      • EWRNewark Liberty International Airport 12:02
        BOSBoston Logan International Airport 15:54
      • 6h 09m (2h 33m)
      • 1 Stop EWR · New York City 2h 33m
      • United Airlines (UA 782)Boeing 737 Max 9 Passenger
        United Airlines (UA 1176)Boeing 737 Max 8 Passenger
      • United Airlines (UA 782)
        • M
        • -
        • W
        • T
        • F
        • -
        • -
      • 08:45 ORD
        15:54 BOS
        6Hrs, 09m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 08:45 - BOS 15:54 6h 09m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 08:45
        EWRNewark Liberty International Airport 14:35
      • EWRNewark Liberty International Airport 12:02
        BOSBoston Logan International Airport 15:54
      • 6h 09m (2h 33m)
      • 1 Stop EWR · New York City 2h 33m
      • United Airlines (UA 782)Boeing 737 900
        United Airlines (UA 1176)Boeing 737 Max 8 Passenger
      • United Airlines (UA 782)
        • -
        • T
        • -
        • -
        • -
        • S
        • S
      • 08:50 ORD
        14:19 BOS
        4Hrs, 29m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 08:50 - BOS 14:19 4h 29m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 08:50
        IADWashington Dulles International Airport 12:40
      • IADWashington Dulles International Airport 11:49
        BOSBoston Logan International Airport 14:19
      • 4h 29m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 2029)Boeing 757 200 Series
        United Airlines (UA 1709)Boeing 737 900
      • United Airlines (UA 2029)
        • M
        • T
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        • T
        • F
        • S
        • S
      • 09:10 MDW
        14:35 BOS
        4Hrs, 25m 1 Stop (BWI)
      • MDWChicago Midway Airport 09:10 - BOS 14:35 4h 25m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 09:10
        BWIBaltimore Washington International Airport 13:05
      • BWIBaltimore Washington International Airport 12:00
        BOSBoston Logan International Airport 14:35
      • 4h 25m (1h 05m)
      • 1 Stop BWI · Baltimore 1h 05m
      • Southwest Airlines (WN 3299)Boeing 737 800
        Southwest Airlines (WN 3948)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3299)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 09:45 ORD
        15:38 BOS
        4Hrs, 53m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 09:45 - BOS 15:38 4h 53m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 09:45
        PHLPhiladelphia International Airport 14:15
      • PHLPhiladelphia International Airport 12:42
        BOSBoston Logan International Airport 15:38
      • 4h 53m (1h 33m)
      • 1 Stop PHL · Philadelphia 1h 33m
      • American Airlines (AA 2098)Airbus
        American Airlines (AA 1496)Airbus
      • American Airlines (AA 2098)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 09:50 MDW
        16:50 BOS
        6Hrs, 00m 1 Stop (BWI)
      • MDWChicago Midway Airport 09:50 - BOS 16:50 6h 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 09:50
        BWIBaltimore Washington International Airport 15:20
      • BWIBaltimore Washington International Airport 12:40
        BOSBoston Logan International Airport 16:50
      • 6h (2h 40m)
      • 1 Stop BWI · Baltimore 2h 40m
      • Southwest Airlines (WN 3299)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 965)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3299)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
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      What’s the fastest flight time from Chicago to Boston?

      The fastest flight time for direct flights from Chicago to Boston is 2 hours 15 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Chicago to Boston?

      The most popular airline flying from Chicago to Boston is Southwest Airlines. Find the latest flight deals on Wego.

      How far is Boston from Chicago?

      The flight distance between Chicago and Boston is 1366km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:00. The last flight of the day departs at 19:20. See the full list of flight times on Wego.

      How many airlines offer direct flights from Chicago to Boston?

      There are 4 airlines that offer direct flights from Chicago to Boston. Find out the list of airlines on Wego.

      All Airports in Boston

      Boston Logan International Airport BOS

      Popular Airlines Flying From Chicago to Boston

      Southwest Airlines ‏()

      Popular Destinations From Boston

      Popular Destinations From Chicago

      Popular Hotels in Boston

      Hotels In Popular Destinations