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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • any
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • price
  • month of departure
  • month of return
$67
outward: Sep 11, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 15, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$67
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 18, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$67
outward: Sep 8, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 11, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$67
outward: Sep 8, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 11, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$74
outward: Sep 5, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
inbound: Sep 8, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$76
outward: Oct 17, 2018
5:05a ORD » 7:19a BOS
American Airlines direct (2h14m)
inbound: Oct 25, 2018
11:00a BOS » 1:49p ORD
American Airlines direct (2h49m)
$76
outward: Sep 20, 2018
5:05a ORD » 7:21a BOS
American Airlines direct (2h16m)
inbound: Sep 26, 2018
11:00a BOS » 1:44p ORD
American Airlines direct (2h44m)
$76
outward: Oct 17, 2018
5:05a ORD » 7:19a BOS
American Airlines direct (2h14m)
inbound: Oct 25, 2018
11:00a BOS » 1:49p ORD
American Airlines direct (2h49m)
$78
outward: Oct 30, 2018
4:05a ORD » 6:19a BOS
American Airlines direct (2h14m)
inbound: Nov 7, 2018
11:00a BOS » 1:54p ORD
American Airlines direct (2h54m)
$78
outward: Oct 13, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 17, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 18, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 18, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 22, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 25, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 19, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 19, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 19, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 19, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 19, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 19, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 19, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 12, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 19, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Sep 22, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 25, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$78
outward: Aug 28, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
inbound: Sep 4, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$78
outward: Aug 28, 2018
9:10p ORD » 11:38p BOS
Spirit Airlines direct (2h28m)
inbound: Sep 4, 2018
6:45p BOS » 9:29p ORD
Spirit Airlines direct (2h44m)
$78
outward: Sep 11, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 15, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$79
outward: Sep 15, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 18, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$79
outward: Oct 13, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 17, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$79
outward: Oct 13, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 17, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$79
outward: Sep 19, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Sep 25, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$82
outward: Oct 13, 2018
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
inbound: Oct 17, 2018
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
Return
Departure
07 September Sep Friday $retDate.dayShortName
08 September Sep Saturday $retDate.dayShortName
09 September Sep Sunday $retDate.dayShortName
10 September Sep Monday $retDate.dayShortName
11 September Sep Tuesday $retDate.dayShortName
12 September Sep Wednesday $retDate.dayShortName
13 September Sep Thursday $retDate.dayShortName
01 September Sep Saturday $outDate.dayShortName
$150 $137 $179 $160 $113 $113 $126
02 September Sep Sunday $outDate.dayShortName
$259 $184 $158 $184 $220 $161 $233
03 September Sep Monday $outDate.dayShortName
$244 $244 $257
04 September Sep Tuesday $outDate.dayShortName
$117 $117 $160 $222 $118 $118 $118
05 September Sep Wednesday $outDate.dayShortName
$88 $73 $90 $99 $86 $88 $86
06 September Sep Thursday $outDate.dayShortName
$112 $99 $86 $95 $86 $101 $101
07 September Sep Friday $outDate.dayShortName
$99 $88 $102 $101 $100 $114
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
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • all
  • Alaska Airlines
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Oct 3, 2018
Spirit Airlines direct
return: Oct 10, 2018
Spirit Airlines direct
JetBlue
outbound: Sep 5, 2018
JetBlue direct
return: Sep 7, 2018
JetBlue direct
Southwest Airlines
outbound: Sep 12, 2018
Southwest Airlines direct
return: Sep 18, 2018
Spirit Airlines direct
United Airlines
outbound: Sep 6, 2018
United Airlines direct
return: Sep 9, 2018
United Airlines direct
Delta Air Lines
outbound: Jul 5, 2019
Delta Air Lines 1 stop
return: Jul 11, 2019
Delta Air Lines 1 stop
American Airlines
outbound: Nov 21, 2018
American Airlines direct
return: Nov 27, 2018
American Airlines direct
Alaska Airlines
outbound: Oct 3, 2018
Alaska Airlines 1 stop
return: Oct 11, 2018
Spirit Airlines direct

Travel tips for flights Chicago - Boston

Average flight duration: 2h39m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Aug 21, 2018 1:19 PM, GMT-4
  • Weather:
  • min. 59ºF, max. 75ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Aug 21, 2018 12:19 PM, GMT-5
  • Weather:
  • min. 62ºF, max. 75ºF