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

Find cheap airline tickets from Boston to Chicago by date

  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • price
  • month of departure
  • month of return
$83
outward: Sep 11, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 18, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$115
outward: Sep 16, 2018
12:40p BOS » 3:25p ORD
JetBlue direct (2h45m)
inbound: Sep 27, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$120
outward: Sep 21, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$120
outward: Sep 21, 2018
6:45p BOS » 9:36p ORD
Spirit Airlines direct (2h51m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
25 days ago
$121
outward: Oct 13, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 14, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
37 hours ago
$122
outward: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 23, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
Verify
4 days ago
$122
outward: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 24, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
Verify
4 days ago
$122
outward: Aug 21, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 25, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
Verify
4 days ago
$122
outward: Aug 22, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 23, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
Verify
4 days ago
$122
outward: Aug 22, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 24, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
Verify
4 days ago
$122
outward: Aug 22, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
inbound: Aug 25, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
Verify
4 days ago
$128
outward: Sep 21, 2018
2:02p BOS » 4:55p ORD
American Airlines direct (2h53m)
inbound: Sep 25, 2018
5:05a ORD » 7:21a BOS
American Airlines direct (2h16m)
Verify
18 days ago
$128
outward: Sep 10, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$128
outward: Sep 10, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 18, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$128
outward: Sep 10, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 19, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$128
outward: Sep 11, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$128
outward: Sep 11, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 19, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$128
outward: Sep 12, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 17, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$128
outward: Sep 12, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 18, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$128
outward: Sep 12, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 19, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
29 hours ago
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
19 days ago
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
18 days ago
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
20 days ago
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
22 days ago
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
22 days ago
$130
outward: Sep 21, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
21 days ago
$145
outward: Jul 24, 2018
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
inbound: Jul 27, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
Verify
12 days ago
$159
outward: Jul 24, 2018
2:35a BOS » 5:25a ORD
JetBlue direct (2h50m)
inbound: Sep 24, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
2 days ago
$160
outward: Jul 25, 2018
1:00p BOS » 3:50p ORD
JetBlue direct (2h50m)
inbound: Jul 25, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
Verify
20 days ago
$160
outward: Jul 25, 2018
1:00p BOS » 3:50p ORD
JetBlue direct (2h50m)
inbound: Jul 25, 2018
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
Verify
20 days ago
Return
Departure
01 August Aug Wednesday $retDate.dayShortName
02 August Aug Thursday $retDate.dayShortName
03 August Aug Friday $retDate.dayShortName
04 August Aug Saturday $retDate.dayShortName
05 August Aug Sunday $retDate.dayShortName
06 August Aug Monday $retDate.dayShortName
07 August Aug Tuesday $retDate.dayShortName
26 July Jul Thursday $outDate.dayShortName
27 July Jul Friday $outDate.dayShortName
28 July Jul Saturday $outDate.dayShortName
29 July Jul Sunday $outDate.dayShortName
$214 $170 $170
30 July Jul Monday $outDate.dayShortName
$244 $220 $232 $182
31 July Jul Tuesday $outDate.dayShortName
$244 $200 $232 $189 $189
01 August Aug Wednesday $outDate.dayShortName
$234 $210 $234
Availability of fares is not guaranteed for offers found in the last 7 days.
Choose when you'd like to depart to Chicago (USA):
*Best price per person, all taxes and surcharges included; found in the last 14 days on liligo.com
Find the cheapest Boston Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Boston - Chicago with these new dates, click on an offer. Want to depart from another city? Choose: Las Vegas - Chicago New York - Chicago London - Chicago Miami - Chicago San Francisco - Chicago See more routes

Airlines operating flights from Boston to Chicago

  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • all
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Oct 12, 2018
Spirit Airlines direct
return: Oct 14, 2018
Spirit Airlines direct
$162 Verify
40 hours ago
JetBlue
outbound: Jul 24, 2018
JetBlue direct
return: Jul 27, 2018
Spirit Airlines direct
$167 Verify
12 days ago
Southwest Airlines
outbound: Jul 24, 2018
Southwest Airlines direct
return: Jul 27, 2018
Southwest Airlines 1 stop
$224 Verify
12 days ago
American Airlines
outbound: Aug 30, 2018
American Airlines direct
return: Sep 3, 2018
American Airlines direct
$206 Verify
2 days ago
United Airlines
outbound: Aug 30, 2018
United Airlines direct
return: Sep 3, 2018
Delta Air Lines 1 stop
$214 Verify
2 days ago
Delta Air Lines
outbound: Jul 31, 2018
Delta Air Lines 1 stop
return: Aug 4, 2018
Delta Air Lines 1 stop
$225 Verify
3 days ago
Airline tickets Boston - Chicago found in the last 30 days.

Travel tips for flights Boston - Chicago

Average flight duration: 2h33m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 21, 2018 10:16 PM, GMT-5
  • Weather:
  • min. 67ºF, max. 75ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jul 21, 2018 11:16 PM, GMT-4
  • Weather:
  • min. 71ºF, max. 77ºF