Take off on cheap flights from Chicago to Boston, your adventure starts now!

Find cheap airline tickets from Chicago to Boston by date

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  • May 2022
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  • August 2022
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  • October 2022
  • November 2022
  • December 2022
  • January 2023
  • February 2023
  • March 2023
  • April 2023
  • any
  • May 2022
  • June 2022
  • July 2022
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  • October 2022
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  • January 2023
  • February 2023
  • March 2023
  • April 2023
  • price
  • month of departure
  • month of return
$227
United Airlines outward: May 29, 2022
4:39a ORD » 7:00a BOS
United Airlines direct (2h21m)
Frontier Airlines inbound: May 30, 2022
5:31p BOS » 3:34p MDW
Frontier Airlines 1 stop (22h03m)
$252
Delta Air Lines outward: May 29, 2022
1:10a MDW » 6:51a BOS
Delta Air Lines 1 stop (5h41m)
Delta Air Lines inbound: Jun 1, 2022
3:59a BOS » 2:47p ORD
Delta Air Lines 1 stop (10h48m)
$255
United Airlines outward: May 29, 2022
4:39a ORD » 7:00a BOS
United Airlines direct (2h21m)
Unknown Company inbound: Jun 1, 2022
1:25a BOS » 5:39p MDW
Unknown Company 1 stop (16h14m)
$295
United Airlines outward: May 29, 2022
4:39a ORD » 7:00a BOS
United Airlines direct (2h21m)
Unknown Company inbound: May 30, 2022
12:15p BOS » 1:30p ORD
Unknown Company 1 stop (25h15m)
$307
Delta Air Lines outward: Jul 19, 2022
3:15a ORD » 5:47a BOS
Delta Air Lines direct (2h32m)
Spirit Airlines inbound: Jul 21, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)
$310
United Airlines outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)
Spirit Airlines inbound: Jul 21, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)
$328
Spirit Airlines outward: Jul 18, 2022
6:05p ORD » 1:46a BOS
Spirit Airlines 1 stop (7h41m)
Spirit Airlines inbound: Jul 21, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)
$333
United Airlines outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$333
United Airlines outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$338
Spirit Airlines outward: Jul 7, 2022
6:05p ORD » 1:46a BOS
Spirit Airlines 1 stop (7h41m)
Spirit Airlines inbound: Jul 10, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)
$340
United Airlines outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)
American Airlines inbound: Jul 21, 2022
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)
$340
United Airlines outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)
American Airlines inbound: Jul 21, 2022
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)
$341
Spirit Airlines outward: Jul 18, 2022
6:05p ORD » 1:46a BOS
Spirit Airlines 1 stop (7h41m)
Spirit Airlines inbound: Jul 21, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)
$358
Delta Air Lines outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)
American Airlines inbound: Jul 21, 2022
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)
$359
Delta Air Lines outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)
American Airlines inbound: Jul 21, 2022
6:33p BOS » 9:24p ORD
American Airlines direct (2h51m)
$361
Delta Air Lines outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$361
Spirit Airlines outward: May 27, 2022
12:15p ORD » 11:24p BOS
Spirit Airlines 1 stop (11h09m)
Spirit Airlines inbound: May 31, 2022
2:30p BOS » 10:07p ORD
Spirit Airlines 1 stop (7h37m)
$364
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$367
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
Unknown Company inbound: Jul 21, 2022
4:55p BOS » 1:32a MDW
Unknown Company 1 stop (8h37m)
$367
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
Unknown Company inbound: Jul 21, 2022
4:55p BOS » 1:32a MDW
Unknown Company 1 stop (8h37m)
$367
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
Unknown Company inbound: Jul 21, 2022
4:55p BOS » 1:32a MDW
Unknown Company 1 stop (8h37m)
$382
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$382
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$383
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$383
JetBlue outward: Jul 19, 2022
2:45a ORD » 5:11a BOS
JetBlue direct (2h26m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$390
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$391
Delta Air Lines outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$396
Delta Air Lines outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
$398
Allegiant Air outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)
JetBlue inbound: Jul 21, 2022
12:15p BOS » 3:11p ORD
JetBlue direct (2h56m)
$399
Delta Air Lines outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)
Delta Air Lines inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)
Return
Departure
Choose when you'd like to depart to Boston (USA):
Find the cheapest Chicago Boston flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - Boston with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to Boston

  • any
  • May 2022
  • June 2022
  • July 2022
  • August 2022
  • September 2022
  • October 2022
  • November 2022
  • December 2022
  • January 2023
  • February 2023
  • March 2023
  • April 2023
  • all
  • American Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: May 28, 2022
Spirit Airlines 1 stop
return: May 31, 2022
Spirit Airlines 1 stop
United Airlines
outbound: May 27, 2022
United Airlines direct
return: May 31, 2022
JetBlue 1 stop
American Airlines
outbound: Jul 7, 2022
American Airlines 1 stop
return: Jul 10, 2022
Spirit Airlines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 2h21m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Boston Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • May 22, 2022 10:21 AM, GMT-4
  • Weather:
  • min. 63ºF, max. 84ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 22, 2022 9:21 AM, GMT-5
  • Weather:
  • min. 50ºF, max. 59ºF