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

Find cheap airline tickets from Boston to Chicago by date

  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • price
  • month of departure
  • month of return
$87
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 6, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$87
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 6, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$87
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 7, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$87
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 7, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$87
outward: Oct 17, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 20, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$88
outward: Sep 26, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$88
outward: Sep 26, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 3, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
$90
outward: Sep 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
$99
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
$100
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
$100
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
$100
outward: Oct 18, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 20, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$101
outward: Sep 26, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 1, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$101
outward: Sep 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 3, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$114
outward: Sep 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 1, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$114
outward: Oct 4, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 9, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$115
outward: Oct 28, 2018
5:45p BOS » 8:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 6, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$115
outward: Oct 28, 2018
5:45p BOS » 8:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 7, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$129
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 8, 2018
12:45p ORD » 2:56p BOS
JetBlue direct (2h11m)
$129
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 9, 2018
12:45p ORD » 2:56p BOS
JetBlue direct (2h11m)
$132
outward: Dec 4, 2018
2:42a BOS » 5:30a ORD
JetBlue direct (2h48m)
inbound: Dec 13, 2018
7:01p ORD » 9:15p BOS
JetBlue direct (2h14m)
$149
outward: Nov 8, 2018
12:51p BOS » 3:47p ORD
JetBlue direct (2h56m)
inbound: Nov 15, 2018
12:45p ORD » 2:56p BOS
JetBlue direct (2h11m)
$149
outward: Oct 17, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 22, 2018
12:15p ORD » 8:35p BOS
Spirit Airlines 1 stop (8h20m)
$152
outward: Sep 28, 2018
9:35p BOS » 7:16a ORD
Spirit Airlines 1 stop (9h41m)
inbound: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$152
outward: Sep 28, 2018
9:35p BOS » 7:16a ORD
Spirit Airlines 1 stop (9h41m)
inbound: Oct 3, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Return
Departure
28 September Sep Friday $retDate.dayShortName
29 September Sep Saturday $retDate.dayShortName
30 September Sep Sunday $retDate.dayShortName
01 October Oct Monday $retDate.dayShortName
02 October Oct Tuesday $retDate.dayShortName
03 October Oct Wednesday $retDate.dayShortName
04 October Oct Thursday $retDate.dayShortName
23 September Sep Sunday $outDate.dayShortName
24 September Sep Monday $outDate.dayShortName
25 September Sep Tuesday $outDate.dayShortName
26 September Sep Wednesday $outDate.dayShortName
$101 $88 $88
27 September Sep Thursday $outDate.dayShortName
$114 $90 $101
28 September Sep Friday $outDate.dayShortName
$164 $151 $151
29 September Sep Saturday $outDate.dayShortName
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: Las Vegas - Chicago New York - Chicago London - Chicago Miami - Chicago San Francisco - Chicago See more routes

Airlines operating flights from Boston to Chicago

  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • all
  • Alaska Airlines
  • Delta Air Lines
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Sep 26, 2018
Spirit Airlines direct
return: Oct 1, 2018
Spirit Airlines direct
JetBlue
outbound: Dec 3, 2018
JetBlue direct
return: Dec 13, 2018
JetBlue direct
United Airlines
outbound: Dec 30, 2018
United Airlines direct
return: Jan 2, 2019
United Airlines direct
Delta Air Lines
outbound: Dec 30, 2018
Delta Air Lines 1 stop
return: Jan 2, 2019
United Airlines direct
Alaska Airlines
outbound: Sep 26, 2018
Alaska Airlines 1 stop
return: Oct 1, 2018
Spirit Airlines direct

Travel tips for flights Boston - Chicago

Average flight duration: 2h37m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 23, 2018 11:12 AM, GMT-5
  • Weather:
  • min. 61ºF, max. 71ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Sep 23, 2018 12:12 PM, GMT-4
  • Weather:
  • min. 53ºF, max. 65ºF