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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • any
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • price
  • month of departure
  • month of return
$5
American Airlines outward: Oct 13, 2019
1:00p ORD » 3:16p BOS
American Airlines direct (2h16m)
American Airlines inbound: Oct 18, 2019
11:00a BOS » 1:41p ORD
American Airlines direct (2h41m)
$5
American Airlines outward: Jul 29, 2019
1:00p ORD » 3:17p BOS
American Airlines direct (2h17m)
American Airlines inbound: Aug 5, 2019
11:50a BOS » 2:38p ORD
American Airlines direct (2h48m)
$130
JetBlue outward: Aug 15, 2019
12:45p ORD » 3:02p BOS
JetBlue direct (2h17m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$130
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$131
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$132
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$132
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$134
JetBlue outward: Aug 15, 2019
12:45p ORD » 3:02p BOS
JetBlue direct (2h17m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$135
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$135
Spirit Airlines outward: Sep 12, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Sep 15, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$135
Spirit Airlines outward: Sep 12, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Sep 15, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$135
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$135
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$136
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$137
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$137
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$138
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$140
Spirit Airlines outward: Aug 15, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 20, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$145
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$145
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$145
Spirit Airlines outward: Nov 9, 2019
9:03p ORD » 11:21p BOS
Spirit Airlines direct (2h18m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:18p ORD
Spirit Airlines direct (2h33m)
$145
Spirit Airlines outward: Nov 9, 2019
9:03p ORD » 11:21p BOS
Spirit Airlines direct (2h18m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:18p ORD
Spirit Airlines direct (2h33m)
$145
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$145
Spirit Airlines outward: Aug 7, 2019
9:16p ORD » 11:45p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Aug 13, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$145
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$145
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$145
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$145
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$145
Spirit Airlines outward: Nov 9, 2019
9:03p ORD » 11:21p BOS
Spirit Airlines direct (2h18m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:18p ORD
Spirit Airlines direct (2h33m)
$146
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
Return
Departure
08 August Aug Thursday $retDate.dayShortName
09 August Aug Friday $retDate.dayShortName
10 August Aug Saturday $retDate.dayShortName
11 August Aug Sunday $retDate.dayShortName
12 August Aug Monday $retDate.dayShortName
13 August Aug Tuesday $retDate.dayShortName
14 August Aug Wednesday $retDate.dayShortName
04 August Aug Sunday $outDate.dayShortName
05 August Aug Monday $outDate.dayShortName
$251
06 August Aug Tuesday $outDate.dayShortName
$203 $228
07 August Aug Wednesday $outDate.dayShortName
$140
08 August Aug Thursday $outDate.dayShortName
$211 $238
09 August Aug Friday $outDate.dayShortName
$155
10 August Aug Saturday $outDate.dayShortName
$178
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
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • all
  • Alaska Airlines
  • American Airlines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Aug 6, 2019
Spirit Airlines direct
return: Aug 9, 2019
Spirit Airlines direct
JetBlue
outbound: Aug 30, 2019
JetBlue direct
return: Sep 2, 2019
JetBlue direct
Southwest Airlines
outbound: Aug 9, 2019
Southwest Airlines 1 stop
return: Aug 14, 2019
Spirit Airlines direct
American Airlines
outbound: Aug 7, 2019
American Airlines 1 stop
return: Aug 13, 2019
American Airlines 1 stop
United Airlines
outbound: Dec 12, 2019
United Airlines direct
return: Dec 17, 2019
United Airlines direct
Alaska Airlines
outbound: Dec 12, 2019
Alaska Airlines 1 stop
return: Dec 17, 2019
Alaska Airlines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 2h37m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jul 17, 2019 6:42 AM, GMT-4
  • Weather:
  • min. 69ºF, max. 80ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 17, 2019 5:42 AM, GMT-5
  • Weather:
  • min. 76ºF, max. 88ºF