en USA

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)
Verify
11 days ago
$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)
Verify
12 days ago
$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)
Verify
6 days ago
$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)
Verify
12 days ago
$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)
Verify
6 days ago
$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)
Verify
12 days ago
$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)
Verify
19 days ago
$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)
Verify
13 hours ago
$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)
Verify
6 days ago
$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)
Verify
7 days ago
$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)
Verify
19 days ago
$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)
Verify
19 days ago
$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)
Verify
19 days ago
$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)
Verify
19 days ago
$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)
Verify
19 days ago
$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)
Verify
19 days ago
$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)
Verify
15 days ago
$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)
Verify
12 hours ago
$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)
Verify
11 days ago
$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)
Verify
6 days ago
$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)
Verify
15 days ago
$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)
Verify
19 days ago
$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)
Verify
19 days ago
$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)
Verify
19 days ago
$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)
Verify
19 days ago
$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)
Verify
6 days ago
$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)
Verify
6 days ago
$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)
Verify
6 days ago
$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)
Verify
6 days ago
$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)
Verify
6 days ago
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
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
  • 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
$116 Verify
18 hours ago
Spirit Airlines
outbound: Jul 18, 2018
Spirit Airlines direct
return: Jul 25, 2018
Spirit Airlines direct
$168 Verify
18 hours ago
Southwest Airlines
outbound: Oct 3, 2018
Southwest Airlines direct
return: Oct 10, 2018
Southwest Airlines direct
$174 Verify
6 days ago
United Airlines
outbound: Jul 18, 2018
United Airlines direct
return: Jul 25, 2018
United Airlines direct
$213 Verify
18 hours ago
American Airlines
outbound: Oct 3, 2018
American Airlines direct
return: Oct 10, 2018
American Airlines direct
$126 Verify
6 days ago
Delta Air Lines
outbound: Oct 3, 2018
Delta Air Lines 1 stop
return: Oct 10, 2018
Delta Air Lines 1 stop
$189 Verify
6 days ago
Airline tickets Chicago - Boston found in the last 30 days.

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