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

Find cheap airline tickets from Boston to Chicago by date

  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • price
  • month of departure
  • month of return
$83
outward: Sep 11, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 18, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$115
outward: Sep 16, 2018
12:40p BOS » 3:25p ORD
JetBlue direct (2h45m)
inbound: Sep 27, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$120
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)
$120
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)
$121
outward: Oct 13, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 14, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$122
outward: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 23, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
$122
outward: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 24, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
$122
outward: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 25, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
$122
outward: Aug 22, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 23, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
$122
outward: Aug 22, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 24, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
$122
outward: Aug 22, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 25, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
$128
outward: Sep 21, 2018
2:02p BOS » 4:55p ORD
American Airlines direct (2h53m)
inbound: Sep 25, 2018
5:05a ORD » 7:21a BOS
American Airlines direct (2h16m)
$128
outward: Sep 10, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$128
outward: Sep 10, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 18, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$128
outward: Sep 10, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 19, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$128
outward: Sep 11, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$128
outward: Sep 11, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 19, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$128
outward: Sep 12, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$128
outward: Sep 12, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 18, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$128
outward: Sep 12, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 19, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$145
outward: Jul 24, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 27, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$159
outward: Jul 24, 2018
2:35a BOS » 5:25a ORD
JetBlue direct (2h50m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
$160
outward: Jul 25, 2018
1:00p BOS » 3:50p ORD
JetBlue direct (2h50m)
inbound: Jul 25, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
$160
outward: Jul 25, 2018
1:00p BOS » 3:50p ORD
JetBlue direct (2h50m)
inbound: Jul 25, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
Return
Departure
01 August Aug Wednesday $retDate.dayShortName
02 August Aug Thursday $retDate.dayShortName
03 August Aug Friday $retDate.dayShortName
04 August Aug Saturday $retDate.dayShortName
05 August Aug Sunday $retDate.dayShortName
06 August Aug Monday $retDate.dayShortName
07 August Aug Tuesday $retDate.dayShortName
26 July Jul Thursday $outDate.dayShortName
27 July Jul Friday $outDate.dayShortName
28 July Jul Saturday $outDate.dayShortName
29 July Jul Sunday $outDate.dayShortName
$214 $170 $170
30 July Jul Monday $outDate.dayShortName
$244 $220 $232 $182
31 July Jul Tuesday $outDate.dayShortName
$244 $200 $232 $189 $189
01 August Aug Wednesday $outDate.dayShortName
$234 $210 $234
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
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • all
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Oct 12, 2018
Spirit Airlines direct
return: Oct 14, 2018
Spirit Airlines direct
JetBlue
outbound: Jul 24, 2018
JetBlue direct
return: Jul 27, 2018
Spirit Airlines direct
Southwest Airlines
outbound: Jul 24, 2018
Southwest Airlines direct
return: Jul 27, 2018
Southwest Airlines 1 stop
American Airlines
outbound: Aug 30, 2018
American Airlines direct
return: Sep 3, 2018
American Airlines direct
United Airlines
outbound: Aug 30, 2018
United Airlines direct
return: Sep 3, 2018
Delta Air Lines 1 stop
Delta Air Lines
outbound: Jul 31, 2018
Delta Air Lines 1 stop
return: Aug 4, 2018
Delta Air Lines 1 stop

Travel tips for flights Boston - Chicago

Average flight duration: 2h33m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 21, 2018 10:16 PM, GMT-5
  • Weather:
  • min. 67ºF, max. 75ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jul 21, 2018 11:16 PM, GMT-4
  • Weather:
  • min. 71ºF, max. 77ºF