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Find cheap airline tickets from Boston to Chicago by date

  • any
  • December 2023
  • January 2024
  • February 2024
  • March 2024
  • April 2024
  • May 2024
  • June 2024
  • July 2024
  • August 2024
  • September 2024
  • October 2024
  • November 2024
  • any
  • December 2023
  • January 2024
  • February 2024
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  • September 2024
  • October 2024
  • November 2024
  • price
  • month of departure
  • month of return
$99
Frontier Airlines outward: Dec 13, 2023
2:33p BOS » 12:41a MDW
Frontier Airlines 1 stop (10h08m)
Frontier Airlines inbound: Dec 18, 2023
12:22a MDW » 2:46p BOS
Frontier Airlines 1 stop (14h24m)
$132
Frontier Airlines outward: Dec 13, 2023
2:33p BOS » 12:41a MDW
Frontier Airlines 1 stop (10h08m)
Frontier Airlines inbound: Dec 17, 2023
3:25a ORD » 2:11p BOS
Frontier Airlines 1 stop (10h46m)
$158
Spirit Airlines outward: Dec 15, 2023
3:37a BOS » 5:50p ORD
Spirit Airlines 1 stop (14h13m)
Spirit Airlines inbound: Dec 17, 2023
2:40p ORD » 5:22p BOS
Spirit Airlines 1 stop (26h42m)
$159
Frontier Airlines outward: Dec 13, 2023
2:33p BOS » 12:41a MDW
Frontier Airlines 1 stop (10h08m)
Frontier Airlines inbound: Dec 17, 2023
3:25a ORD » 2:11p BOS
Frontier Airlines 1 stop (10h46m)
$191
Unknown Company outward: Dec 15, 2023
12:55a BOS » 4:15p ORD
Unknown Company 1 stop (15h20m)
American Airlines inbound: Dec 16, 2023
2:04p ORD » 4:23p BOS
American Airlines direct (2h19m)
$308
JetBlue outward: May 24, 2024
10:06p BOS » 1:11a ORD
JetBlue direct (3h05m)
JetBlue inbound: May 27, 2024
11:06p ORD » 4:00a BOS
JetBlue 1 stop (4h54m)
$308
JetBlue outward: May 24, 2024
10:06p BOS » 1:11a ORD
JetBlue direct (3h05m)
JetBlue inbound: May 27, 2024
11:06p ORD » 4:00a BOS
JetBlue 1 stop (4h54m)
$321
JetBlue outward: May 24, 2024
10:06p BOS » 1:11a ORD
JetBlue direct (3h05m)
JetBlue inbound: May 28, 2024
1:46a ORD » 4:20a BOS
JetBlue direct (2h34m)
$321
JetBlue outward: May 24, 2024
10:06p BOS » 1:11a ORD
JetBlue direct (3h05m)
JetBlue inbound: May 28, 2024
1:46a ORD » 4:20a BOS
JetBlue direct (2h34m)
$388
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$390
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$391
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$393
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$396
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$396
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$396
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$398
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$407
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$407
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$407
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$407
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$408
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$408
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$408
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$408
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$408
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$409
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$410
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$410
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
$410
Sun Country outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)
Sun Country inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)
Return
Departure
Choose when you'd like to depart to Chicago (USA):
Find the cheapest Boston Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Boston - Chicago with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Boston to Chicago

  • any
  • December 2023
  • January 2024
  • February 2024
  • March 2024
  • April 2024
  • May 2024
  • June 2024
  • July 2024
  • August 2024
  • September 2024
  • October 2024
  • November 2024
  • all
  • Delta Air Lines
  • United Airlines
Delta Air Lines
outbound: Dec 13, 2023
Delta Air Lines direct
return: Dec 16, 2023
Delta Air Lines direct
United Airlines
outbound: Dec 13, 2023
United Airlines direct
return: Dec 16, 2023
United Airlines direct

Travel tips for flights Boston - Chicago

Average flight duration: 2h19m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Dec 7, 2023 8:46 PM, GMT-6
  • Weather:
  • min. 37ºF, max. 53ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Boston Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Dec 7, 2023 9:46 PM, GMT-5
  • Weather:
  • min. 28ºF, max. 45ºF