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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
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • price
  • month of departure
  • month of return
$87
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 6, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
20 days ago
$87
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 6, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
21 days ago
$87
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 7, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
20 days ago
$87
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 7, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
20 days ago
$87
outward: Oct 17, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 20, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
19 days ago
$88
outward: Sep 26, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$88
outward: Sep 26, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 3, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
Verify
21 days ago
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
Verify
25 days ago
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
Verify
28 days ago
$90
outward: Sep 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
Verify
27 days ago
$90
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$99
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
Verify
24 days ago
$100
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
Verify
22 days ago
$100
outward: Oct 23, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 29, 2018
7:51p ORD » 10:21p BOS
Spirit Airlines direct (2h30m)
Verify
23 days ago
$100
outward: Oct 18, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 20, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
19 days ago
$101
outward: Sep 26, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 1, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$101
outward: Sep 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 3, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$114
outward: Sep 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 1, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$114
outward: Oct 4, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 9, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$115
outward: Oct 28, 2018
5:45p BOS » 8:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 6, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
20 days ago
$115
outward: Oct 28, 2018
5:45p BOS » 8:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 7, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
20 days ago
$129
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 8, 2018
12:45p ORD » 2:56p BOS
JetBlue direct (2h11m)
Verify
21 days ago
$129
outward: Oct 27, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Nov 9, 2018
12:45p ORD » 2:56p BOS
JetBlue direct (2h11m)
Verify
20 days ago
$132
outward: Dec 4, 2018
2:42a BOS » 5:30a ORD
JetBlue direct (2h48m)
inbound: Dec 13, 2018
7:01p ORD » 9:15p BOS
JetBlue direct (2h14m)
Verify
24 days ago
$149
outward: Nov 8, 2018
12:51p BOS » 3:47p ORD
JetBlue direct (2h56m)
inbound: Nov 15, 2018
12:45p ORD » 2:56p BOS
JetBlue direct (2h11m)
Verify
24 days ago
$149
outward: Oct 17, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
inbound: Oct 22, 2018
12:15p ORD » 8:35p BOS
Spirit Airlines 1 stop (8h20m)
Verify
19 days ago
$152
outward: Sep 28, 2018
9:35p BOS » 7:16a ORD
Spirit Airlines 1 stop (9h41m)
inbound: Oct 2, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
$152
outward: Sep 28, 2018
9:35p BOS » 7:16a ORD
Spirit Airlines 1 stop (9h41m)
inbound: Oct 3, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Verify
26 days ago
Return
Departure
28 September Sep Friday $retDate.dayShortName
29 September Sep Saturday $retDate.dayShortName
30 September Sep Sunday $retDate.dayShortName
01 October Oct Monday $retDate.dayShortName
02 October Oct Tuesday $retDate.dayShortName
03 October Oct Wednesday $retDate.dayShortName
04 October Oct Thursday $retDate.dayShortName
23 September Sep Sunday $outDate.dayShortName
24 September Sep Monday $outDate.dayShortName
25 September Sep Tuesday $outDate.dayShortName
26 September Sep Wednesday $outDate.dayShortName
$101 $88 $88
27 September Sep Thursday $outDate.dayShortName
$114 $90 $101
28 September Sep Friday $outDate.dayShortName
$164 $151 $151
29 September Sep Saturday $outDate.dayShortName
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
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • all
  • Alaska Airlines
  • Delta Air Lines
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Sep 26, 2018
Spirit Airlines direct
return: Oct 1, 2018
Spirit Airlines direct
$101 Verify
29 days ago
JetBlue
outbound: Dec 3, 2018
JetBlue direct
return: Dec 13, 2018
JetBlue direct
$132 Verify
24 days ago
United Airlines
outbound: Dec 30, 2018
United Airlines direct
return: Jan 2, 2019
United Airlines direct
$243 Verify
21 days ago
Delta Air Lines
outbound: Dec 30, 2018
Delta Air Lines 1 stop
return: Jan 2, 2019
United Airlines direct
$258 Verify
21 days ago
Alaska Airlines
outbound: Sep 26, 2018
Alaska Airlines 1 stop
return: Oct 1, 2018
Spirit Airlines direct
$334 Verify
29 days ago
Airline tickets Boston - Chicago found in the last 30 days.

Travel tips for flights Boston - Chicago

Average flight duration: 2h37m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 23, 2018 11:12 AM, GMT-5
  • Weather:
  • min. 61ºF, max. 71ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Sep 23, 2018 12:12 PM, GMT-4
  • Weather:
  • min. 53ºF, max. 65ºF