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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)
Verify
9 days ago
$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)
Verify
8 days ago
$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)
Verify
6 days ago
$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)
Verify
23 days ago
$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)
Verify
3 days ago
$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)
Verify
2 days ago
$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)
Verify
10 days ago
$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)
Verify
17 hours ago
$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)
Verify
20 days ago
$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)
Verify
19 days ago
$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)
Verify
18 days ago
$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)
Verify
5 days ago
$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)
Verify
5 days ago
$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)
Verify
4 days ago
$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)
Verify
9 days ago
$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)
Verify
17 days ago
$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)
Verify
7 days ago
$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)
Verify
42 hours ago
$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)
Verify
17 days ago
$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)
Verify
7 days ago
$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)
Verify
4 days ago
$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)
Verify
17 days ago
$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)
Verify
3 days ago
$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)
Verify
17 days ago
$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)
Verify
17 days ago
$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)
Verify
4 days ago
$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)
Verify
2 days ago
$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)
Verify
10 days ago
$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)
Verify
8 days ago
$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)
Verify
6 days ago
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
Availability of fares is not guaranteed for offers found in the last 7 days.
Choose when you'd like to depart to Boston (USA):
*Best price per person, all taxes and surcharges included; found in the last 14 days on liligo.com
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
$264 Verify
2 days ago
Southwest Airlines
outbound: Jul 27, 2018
Southwest Airlines direct
return: Jul 29, 2018
Southwest Airlines 1 stop
$283 Verify
2 days ago
JetBlue
outbound: Jul 2, 2018
JetBlue direct
return: Jul 9, 2018
JetBlue direct
$164 Verify
5 days ago
United Airlines
outbound: Jul 27, 2018
United Airlines direct
return: Jul 29, 2018
United Airlines direct
$260 Verify
2 days ago
American Airlines
outbound: Jul 27, 2018
American Airlines direct
return: Jul 29, 2018
American Airlines direct
$284 Verify
2 days ago
Delta Air Lines
outbound: Jun 26, 2018
Delta Air Lines 1 stop
return: Jul 3, 2018
Spirit Airlines direct
$161 Verify
4 days ago
Airline tickets Chicago - Boston found in the last 30 days.

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