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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
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  • April 2020
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  • June 2020
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  • any
  • October 2019
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  • price
  • month of departure
  • month of return
$73
Spirit Airlines outward: Nov 9, 2019
9:20p ORD » 11:48p BOS
Spirit Airlines direct (2h28m)
Spirit Airlines inbound: Nov 13, 2019
7:25p BOS » 10:20p ORD
Spirit Airlines direct (2h55m)
$73
Spirit Airlines outward: Nov 9, 2019
9:20p ORD » 11:48p BOS
Spirit Airlines direct (2h28m)
Spirit Airlines inbound: Nov 13, 2019
7:25p BOS » 10:20p ORD
Spirit Airlines direct (2h55m)
$110
Spirit Airlines outward: Nov 9, 2019
9:20p ORD » 11:48p BOS
Spirit Airlines direct (2h28m)
JetBlue inbound: Nov 14, 2019
4:55a BOS » 7:39a ORD
JetBlue direct (2h44m)
$128
Spirit Airlines outward: Dec 7, 2019
3:40a ORD » 1:29p BOS
Spirit Airlines 1 stop (9h49m)
Spirit Airlines inbound: Dec 9, 2019
4:26a BOS » 1:55p ORD
Spirit Airlines 1 stop (9h29m)
$163
Spirit Airlines outward: Dec 7, 2019
3:45a ORD » 1:33p BOS
Spirit Airlines 1 stop (9h48m)
Spirit Airlines inbound: Dec 9, 2019
3:45a BOS » 2:17p ORD
Spirit Airlines 1 stop (10h32m)
$169
Spirit Airlines outward: Oct 24, 2019
9:20p ORD » 11:48p BOS
Spirit Airlines direct (2h28m)
Spirit Airlines inbound: Oct 27, 2019
6:25p BOS » 9:20p ORD
Spirit Airlines direct (2h55m)
$430
Delta Air Lines outward: Oct 31, 2019
2:48p ORD » 5:23p BOS
Delta Air Lines direct (2h35m)
Delta Air Lines inbound: Nov 8, 2019
1:55a BOS » 4:59a ORD
Delta Air Lines direct (3h04m)
Return
Departure
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Airlines operating flights from Chicago to Boston

  • any
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
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  • September 2020
  • all
  • Spirit Airlines
Spirit Airlines
outbound: Dec 6, 2019
Spirit Airlines 1 stop
return: Dec 8, 2019
Spirit Airlines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 2h38m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Oct 15, 2019 12:06 AM, GMT-4
  • Weather:
  • min. 49ºF, max. 62ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Oct 14, 2019 11:06 PM, GMT-5
  • Weather:
  • min. 48ºF, max. 54ºF