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

Find cheap airline tickets from Boston to Chicago by date

  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • price
  • month of departure
  • month of return
$114
outward: May 23, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: May 26, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$129
outward: May 24, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: May 26, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$140
outward: Oct 9, 2018
11:45a BOS » 2:25p MDW
Southwest Airlines direct (2h40m)
inbound: Oct 17, 2018
3:20a MDW » 5:35a BOS
Southwest Airlines direct (2h15m)
$142
outward: Sep 21, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$142
outward: Sep 21, 2018
11:00a BOS » 1:50p ORD
American Airlines direct (2h50m)
inbound: Sep 25, 2018
4:45a ORD » 7:04a BOS
American Airlines direct (2h19m)
$144
outward: May 24, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: May 27, 2018
2:50p ORD » 5:05p BOS
United Airlines direct (2h15m)
$151
outward: May 23, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: May 27, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$162
outward: Oct 8, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 15, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$162
outward: Oct 8, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 16, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$162
outward: Oct 8, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$162
outward: Oct 9, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 15, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$162
outward: Oct 9, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$162
outward: Oct 10, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 15, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$162
outward: Oct 10, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 16, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$162
outward: Oct 10, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$165
outward: Jul 2, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 4, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$165
outward: Jul 2, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 4, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$165
outward: Jul 2, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 5, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$165
outward: Jul 2, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 5, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$175
outward: Jul 2, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 6, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$175
outward: Jul 2, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 6, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$181
outward: Oct 7, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 13, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$182
outward: Jul 28, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Aug 4, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$183
outward: Jul 1, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 5, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
$185
outward: Jul 2, 2018
2:35a BOS » 5:25a ORD
JetBlue direct (2h50m)
inbound: Jul 5, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
$186
outward: Jul 26, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Aug 4, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$186
outward: Jul 28, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Aug 6, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$190
outward: Jul 4, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 9, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$190
outward: Jul 5, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 9, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$191
outward: Oct 7, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Oct 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Return
Departure
23 May May Wednesday $retDate.dayShortName
24 May May Thursday $retDate.dayShortName
25 May May Friday $retDate.dayShortName
26 May May Saturday $retDate.dayShortName
27 May May Sunday $retDate.dayShortName
28 May May Monday $retDate.dayShortName
29 May May Tuesday $retDate.dayShortName
20 May May Sunday $outDate.dayShortName
21 May May Monday $outDate.dayShortName
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$332
23 May May Wednesday $outDate.dayShortName
$114 $150 $261
24 May May Thursday $outDate.dayShortName
$128 $143 $276
25 May May Friday $outDate.dayShortName
$218 $255 $265
26 May May Saturday $outDate.dayShortName
$196 $332
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
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • all
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: May 23, 2018
Spirit Airlines direct
return: May 26, 2018
Spirit Airlines direct
Southwest Airlines
outbound: Oct 9, 2018
Southwest Airlines direct
return: Oct 16, 2018
Southwest Airlines direct
JetBlue
outbound: Oct 9, 2018
JetBlue direct
return: Oct 16, 2018
Delta Air Lines 1 stop
American Airlines
outbound: Oct 9, 2018
American Airlines direct
return: Oct 16, 2018
American Airlines direct
Delta Air Lines
outbound: May 24, 2018
Delta Air Lines 1 stop
return: May 27, 2018
United Airlines direct
United Airlines
outbound: May 24, 2018
United Airlines direct
return: May 27, 2018
United Airlines direct

Travel tips for flights Boston - Chicago

Average flight duration: 2h32m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 20, 2018 10:20 PM, GMT-5
  • Weather:
  • min. 52ºF, max. 58ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • May 20, 2018 11:20 PM, GMT-4