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

Find cheap airline tickets from Chicago to Boston 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
$95
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 21, 2018
3:49p BOS » 6:41p ORD
JetBlue direct (2h52m)
$97
outward: Jul 5, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Jul 10, 2018
2:35a BOS » 5:25a ORD
JetBlue direct (2h50m)
$105
outward: May 31, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 6, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$106
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 22, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$108
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 21, 2018
3:49p BOS » 6:41p ORD
JetBlue direct (2h52m)
$109
outward: Jul 28, 2018
12:20p MDW » 2:30p BOS
Southwest Airlines direct (2h10m)
inbound: Aug 9, 2018
11:35a BOS » 2:10p MDW
Southwest Airlines direct (2h35m)
$109
outward: Aug 22, 2018
1:00p ORD » 3:17p BOS
United Airlines direct (2h17m)
inbound: Aug 29, 2018
11:00a BOS » 1:37p ORD
United Airlines direct (2h37m)
$112
outward: Jul 18, 2018
12:45p ORD » 3:01p BOS
JetBlue direct (2h16m)
inbound: Jul 26, 2018
2:35a BOS » 5:25a ORD
JetBlue direct (2h50m)
$112
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 22, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$113
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 22, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$115
outward: Aug 21, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 28, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$115
outward: Aug 21, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 29, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$115
outward: Aug 22, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 28, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$116
outward: Aug 23, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 28, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$116
outward: Aug 23, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 29, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$118
outward: Aug 15, 2018
5:00a MDW » 7:15a BOS
Southwest Airlines direct (2h15m)
inbound: Aug 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$119
outward: Aug 15, 2018
5:00a MDW » 7:15a BOS
Southwest Airlines direct (2h15m)
inbound: Aug 22, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$120
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$125
outward: May 27, 2018
4:24a ORD » 6:41a BOS
United Airlines direct (2h17m)
inbound: May 31, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$126
outward: Oct 3, 2018
1:00p ORD » 3:16p BOS
American Airlines direct (2h16m)
inbound: Oct 10, 2018
11:00a BOS » 1:50p ORD
American Airlines direct (2h50m)
$128
outward: May 27, 2018
4:36a ORD » 1:28p BOS
Spirit Airlines 1 stop (8h52m)
inbound: May 31, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$131
outward: Aug 21, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 30, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$131
outward: Aug 22, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 30, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$132
outward: Aug 23, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 30, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$138
outward: Jun 19, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 24, 2018
2:35a BOS » 5:25a ORD
JetBlue direct (2h50m)
$141
outward: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 9, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
$141
outward: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 10, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
$141
outward: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 11, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
$141
outward: Oct 3, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 9, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
$141
outward: Oct 3, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 11, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
Return
Departure
20 July Jul Friday $retDate.dayShortName
21 July Jul Saturday $retDate.dayShortName
22 July Jul Sunday $retDate.dayShortName
23 July Jul Monday $retDate.dayShortName
24 July Jul Tuesday $retDate.dayShortName
25 July Jul Wednesday $retDate.dayShortName
26 July Jul Thursday $retDate.dayShortName
13 July Jul Friday $outDate.dayShortName
$210 $195 $214
14 July Jul Saturday $outDate.dayShortName
$229 $214 $234
15 July Jul Sunday $outDate.dayShortName
$214 $200 $219
16 July Jul Monday $outDate.dayShortName
17 July Jul Tuesday $outDate.dayShortName
$167 $167 $182
18 July Jul Wednesday $outDate.dayShortName
$167 $112
19 July Jul Thursday $outDate.dayShortName
$182 $182 $196
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: Las Vegas - Boston New York - Boston London - Boston Miami - Boston San Francisco - Boston See more routes

Airlines operating flights from Chicago to Boston

  • 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
JetBlue
outbound: Jul 18, 2018
JetBlue direct
return: Jul 25, 2018
JetBlue direct
Spirit Airlines
outbound: Jul 18, 2018
Spirit Airlines direct
return: Jul 25, 2018
Spirit Airlines direct
Southwest Airlines
outbound: Oct 3, 2018
Southwest Airlines direct
return: Oct 10, 2018
Southwest Airlines direct
United Airlines
outbound: Jul 18, 2018
United Airlines direct
return: Jul 25, 2018
United Airlines direct
American Airlines
outbound: Oct 3, 2018
American Airlines direct
return: Oct 10, 2018
American Airlines direct
Delta Air Lines
outbound: Oct 3, 2018
Delta Air Lines 1 stop
return: Oct 10, 2018
Delta Air Lines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 2h36m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • May 23, 2018 8:47 AM, GMT-4
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 23, 2018 7:47 AM, GMT-5