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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • any
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • price
  • month of departure
  • month of return
$104
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$105
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$105
outward: Aug 14, 2018
12:45p ORD » 3:01p BOS
JetBlue direct (2h16m)
inbound: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$105
outward: Aug 15, 2018
4:32a ORD » 6:53a BOS
United Airlines direct (2h21m)
inbound: Aug 22, 2018
11:00a BOS » 1:37p ORD
United Airlines direct (2h37m)
$106
outward: Aug 14, 2018
12:45p ORD » 3:01p BOS
JetBlue direct (2h16m)
inbound: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$113
outward: Aug 15, 2018
5:05a ORD » 7:21a BOS
American Airlines direct (2h16m)
inbound: Aug 21, 2018
11:00a BOS » 1:46p ORD
American Airlines direct (2h46m)
$114
outward: Aug 15, 2018
5:05a ORD » 7:21a BOS
American Airlines direct (2h16m)
inbound: Aug 21, 2018
11:00a BOS » 1:46p ORD
American Airlines direct (2h46m)
$114
outward: Aug 15, 2018
5:05a ORD » 7:21a BOS
American Airlines direct (2h16m)
inbound: Aug 21, 2018
2:02p BOS » 4:55p ORD
American Airlines direct (2h53m)
$115
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$115
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 22, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$115
outward: Aug 14, 2018
1:00p ORD » 3:16p BOS
JetBlue direct (2h16m)
inbound: Aug 22, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$116
outward: Aug 15, 2018
5:05a ORD » 7:21a BOS
American Airlines direct (2h16m)
inbound: Aug 21, 2018
2:02p BOS » 4:55p ORD
American Airlines direct (2h53m)
$116
outward: Jun 27, 2018
4:46a ORD » 7:03a BOS
American Airlines direct (2h17m)
inbound: Jul 3, 2018
11:00a BOS » 1:44p ORD
American Airlines direct (2h44m)
$119
outward: Aug 9, 2018
5:05a ORD » 7:21a BOS
American Airlines direct (2h16m)
inbound: Aug 15, 2018
1:51p BOS » 4:57p ORD
American Airlines direct (3h06m)
$122
outward: Aug 8, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 15, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$122
outward: Aug 15, 2018
5:00a MDW » 7:15a BOS
Southwest Airlines direct (2h15m)
inbound: Aug 22, 2018
11:40a BOS » 2:15p MDW
Southwest Airlines direct (2h35m)
$122
outward: Aug 14, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$122
outward: Aug 8, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 15, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$123
outward: Sep 15, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 18, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
$123
outward: Aug 8, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 16, 2018
2:35a BOS » 5:25a ORD
JetBlue direct (2h50m)
$124
outward: Aug 14, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$125
outward: Aug 8, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 13, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$126
outward: Aug 8, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 15, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$126
outward: Sep 13, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 18, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
$126
outward: Sep 15, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 17, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
$126
outward: Jun 27, 2018
4:46a ORD » 7:03a BOS
American Airlines direct (2h17m)
inbound: Jul 3, 2018
11:00a BOS » 1:44p ORD
American Airlines direct (2h44m)
$126
outward: Aug 8, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Aug 15, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$127
outward: Aug 8, 2018
1:00p ORD » 3:16p BOS
Unknown Airline direct (2h16m)
inbound: Aug 15, 2018
11:00a BOS » 1:46p ORD
Unknown Airline direct (2h46m)
$127
outward: Aug 9, 2018
5:05a ORD » 7:21a BOS
Unknown Airline direct (2h16m)
inbound: Aug 15, 2018
11:00a BOS » 1:46p ORD
Unknown Airline direct (2h46m)
$127
outward: Aug 9, 2018
5:05a ORD » 7:21a BOS
Unknown Airline direct (2h16m)
inbound: Aug 15, 2018
11:00a BOS » 1:46p ORD
Unknown Airline direct (2h46m)
Return
Departure
05 August Aug Sunday $retDate.dayShortName
06 August Aug Monday $retDate.dayShortName
07 August Aug Tuesday $retDate.dayShortName
08 August Aug Wednesday $retDate.dayShortName
09 August Aug Thursday $retDate.dayShortName
10 August Aug Friday $retDate.dayShortName
11 August Aug Saturday $retDate.dayShortName
28 July Jul Saturday $outDate.dayShortName
$160
29 July Jul Sunday $outDate.dayShortName
$171
30 July Jul Monday $outDate.dayShortName
$157
31 July Jul Tuesday $outDate.dayShortName
$173 $173
01 August Aug Wednesday $outDate.dayShortName
$160 $207 $159 $159 $207 $177
02 August Aug Thursday $outDate.dayShortName
$209 $207 $153 $159 $207 $177
03 August Aug Friday $outDate.dayShortName
$228 $226 $178 $177 $226 $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
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • all
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jul 27, 2018
Spirit Airlines 1 stop
return: Jul 29, 2018
Spirit Airlines 1 stop
Southwest Airlines
outbound: Jul 27, 2018
Southwest Airlines direct
return: Jul 29, 2018
Southwest Airlines 1 stop
JetBlue
outbound: Jul 2, 2018
JetBlue direct
return: Jul 9, 2018
JetBlue direct
United Airlines
outbound: Jul 27, 2018
United Airlines direct
return: Jul 29, 2018
United Airlines direct
American Airlines
outbound: Jul 27, 2018
American Airlines direct
return: Jul 29, 2018
American Airlines direct
Delta Air Lines
outbound: Jun 26, 2018
Delta Air Lines 1 stop
return: Jul 3, 2018
Spirit Airlines direct

Travel tips for flights Chicago - Boston

Average flight duration: 2h35m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jun 24, 2018 9:02 AM, GMT-4
  • Weather:
  • min. 60ºF, max. 71ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 24, 2018 8:02 AM, GMT-5
  • Weather:
  • min. 64ºF, max. 73ºF