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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • any
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • price
  • month of departure
  • month of return
$148
outward: May 1, 2019
2:20p ORD » 4:38p BOS
American Airlines direct (2h18m)
inbound: May 9, 2019
11:00a BOS » 1:41p ORD
American Airlines direct (2h41m)
$148
outward: May 1, 2019
2:20p ORD » 4:38p BOS
American Airlines direct (2h18m)
inbound: May 9, 2019
11:00a BOS » 1:41p ORD
American Airlines direct (2h41m)
$148
outward: May 1, 2019
2:20p ORD » 4:38p BOS
American Airlines direct (2h18m)
inbound: May 9, 2019
11:00a BOS » 1:41p ORD
American Airlines direct (2h41m)
$160
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 8, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$160
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 9, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$160
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 8, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$160
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 8, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$160
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 9, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$160
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 9, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$165
outward: Mar 8, 2019
2:17p ORD » 4:33p BOS
American Airlines direct (2h16m)
inbound: Mar 11, 2019
1:21a BOS » 4:20a ORD
American Airlines direct (2h59m)
$165
outward: Mar 8, 2019
2:17p ORD » 4:33p BOS
American Airlines direct (2h16m)
inbound: Mar 11, 2019
1:21a BOS » 4:20a ORD
American Airlines direct (2h59m)
$183
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 10, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$183
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 10, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$183
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 10, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$234
outward: May 1, 2019
6:09p ORD » 12:35a BOS
Spirit Airlines 1 stop (6h26m)
inbound: May 8, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$257
outward: May 1, 2019
6:09p ORD » 12:35a BOS
Spirit Airlines 1 stop (6h26m)
inbound: May 10, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$270
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 8, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$270
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 9, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$270
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 8, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$270
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 8, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$270
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 9, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$270
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 9, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$293
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 10, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$293
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 10, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$293
outward: Apr 30, 2019
11:10p ORD » 5:57a BOS
Spirit Airlines 1 stop (6h47m)
inbound: May 10, 2019
6:45p BOS » 9:31p ORD
Spirit Airlines direct (2h46m)
$311
outward: Mar 7, 2019
11:35p ORD » 6:27a BOS
Spirit Airlines 1 stop (6h52m)
inbound: Mar 11, 2019
11:44a BOS » 7:59p ORD
Spirit Airlines 1 stop (8h15m)
$311
outward: Mar 7, 2019
11:35p ORD » 6:27a BOS
Spirit Airlines 1 stop (6h52m)
inbound: Mar 11, 2019
11:44a BOS » 7:59p ORD
Spirit Airlines 1 stop (8h15m)
$364
outward: Mar 7, 2019
11:35p ORD » 6:27a BOS
Spirit Airlines 1 stop (6h52m)
inbound: Mar 9, 2019
4:59p BOS » 12:44a ORD
Spirit Airlines 1 stop (7h45m)
$364
outward: Mar 7, 2019
11:35p ORD » 6:27a BOS
Spirit Airlines 1 stop (6h52m)
inbound: Mar 10, 2019
3:59p BOS » 11:45p ORD
Spirit Airlines 1 stop (7h46m)
$364
outward: Mar 7, 2019
11:35p ORD » 6:27a BOS
Spirit Airlines 1 stop (6h52m)
inbound: Mar 9, 2019
4:59p BOS » 12:44a ORD
Spirit Airlines 1 stop (7h45m)
Return
Departure
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06 May May Monday $retDate.dayShortName
07 May May Tuesday $retDate.dayShortName
08 May May Wednesday $retDate.dayShortName
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27 April Apr Saturday $outDate.dayShortName
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$264 $264 $288
01 May May Wednesday $outDate.dayShortName
$229 $145 $252
02 May May Thursday $outDate.dayShortName
$156 $156 $180
03 May May Friday $outDate.dayShortName
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:

Airlines operating flights from Chicago to Boston

  • any
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • all
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Spirit Airlines
Spirit Airlines
outbound: May 2, 2019
Spirit Airlines direct
return: May 9, 2019
Spirit Airlines direct
JetBlue
outbound: May 1, 2019
JetBlue 1 stop
return: May 9, 2019
Spirit Airlines direct
American Airlines
outbound: May 1, 2019
American Airlines direct
return: May 9, 2019
American Airlines direct
Delta Air Lines
outbound: May 1, 2019
Delta Air Lines 1 stop
return: May 9, 2019
Southwest 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:
  • Jan 18, 2019 11:20 PM, GMT-5
  • Weather:
  • min. 15ºF, max. 30ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jan 18, 2019 10:20 PM, GMT-6
  • Weather:
  • min. 13ºF, max. 20ºF