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 2018
  • February 2018
  • March 2018
  • April 2018
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • any
  • January 2018
  • February 2018
  • March 2018
  • April 2018
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • price
  • month of departure
  • month of return
$119
outward: Feb 6, 2018
4:40p ORD » 6:51p BOS
JetBlue direct (2h11m)
inbound: Feb 13, 2018
4:52p BOS » 7:55p ORD
JetBlue direct (3h03m)
$121
outward: Feb 9, 2018
11:05p ORD » 1:25a BOS
United Airlines direct (2h20m)
inbound: Feb 12, 2018
8:55p BOS » 11:47p ORD
United Airlines direct (2h52m)
$167
outward: Apr 12, 2018
8:19p ORD » 10:47p BOS
Spirit Airlines direct (2h28m)
inbound: Apr 16, 2018
6:45p BOS » 9:33p ORD
Spirit Airlines direct (2h48m)
$169
outward: Mar 15, 2018
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
inbound: Mar 18, 2018
11:58a BOS » 2:58p ORD
JetBlue direct (3h)
$184
outward: Feb 23, 2018
12:52p ORD » 6:23p BOS
Unknown Company 1 stop (5h31m)
inbound: Feb 25, 2018
11:00a BOS » 1:53p ORD
American Airlines direct (2h53m)
$193
outward: Apr 13, 2018
8:19p ORD » 10:47p BOS
Spirit Airlines direct (2h28m)
inbound: Apr 16, 2018
6:45p BOS » 9:33p ORD
Spirit Airlines direct (2h48m)
$194
outward: Apr 12, 2018
1:00p ORD » 3:18p BOS
Unknown Airline direct (2h18m)
inbound: Apr 15, 2018
2:00p BOS » 5:01p ORD
Unknown Airline direct (3h01m)
$218
outward: Apr 12, 2018
8:19p ORD » 10:47p BOS
Spirit Airlines direct (2h28m)
inbound: Apr 14, 2018
6:45p BOS » 9:33p ORD
Spirit Airlines direct (2h48m)
$242
outward: Apr 13, 2018
8:19p ORD » 10:47p BOS
Spirit Airlines direct (2h28m)
inbound: Apr 15, 2018
6:45p BOS » 9:33p ORD
Spirit Airlines direct (2h48m)
$242
outward: Apr 11, 2018
5:58p ORD » 12:45a BOS
Spirit Airlines 1 stop (6h47m)
inbound: Apr 16, 2018
6:45p BOS » 9:33p ORD
Spirit Airlines direct (2h48m)
$244
outward: Apr 13, 2018
8:19p ORD » 10:47p BOS
Spirit Airlines direct (2h28m)
inbound: Apr 14, 2018
6:45p BOS » 9:33p ORD
Spirit Airlines direct (2h48m)
$270
outward: Feb 5, 2018
3:10p ORD » 10:24p BOS
Spirit Airlines 1 stop (7h14m)
inbound: Feb 13, 2018
9:30p BOS » 5:55a ORD
Spirit Airlines 1 stop (8h25m)
$270
outward: Feb 7, 2018
3:00p ORD » 1:40a BOS
Spirit Airlines 1 stop (10h40m)
inbound: Feb 13, 2018
9:30p BOS » 5:55a ORD
Spirit Airlines 1 stop (8h25m)
$291
outward: Apr 11, 2018
5:58p ORD » 12:45a BOS
Spirit Airlines 1 stop (6h47m)
inbound: Apr 15, 2018
6:45p BOS » 9:33p ORD
Spirit Airlines direct (2h48m)
$293
outward: Apr 11, 2018
5:58p ORD » 12:45a BOS
Spirit Airlines 1 stop (6h47m)
inbound: Apr 14, 2018
6:45p BOS » 9:33p ORD
Spirit Airlines direct (2h48m)
$333
outward: Feb 5, 2018
3:10p ORD » 10:24p BOS
Spirit Airlines 1 stop (7h14m)
inbound: Feb 14, 2018
11:25p BOS » 6:58a ORD
Spirit Airlines 1 stop (7h33m)
$333
outward: Feb 6, 2018
3:10p ORD » 10:24p BOS
Spirit Airlines 1 stop (7h14m)
inbound: Feb 14, 2018
11:25p BOS » 6:58a ORD
Spirit Airlines 1 stop (7h33m)
$333
outward: Feb 7, 2018
3:00p ORD » 1:40a BOS
Spirit Airlines 1 stop (10h40m)
inbound: Feb 14, 2018
11:25p BOS » 6:58a ORD
Spirit Airlines 1 stop (7h33m)
Return
Departure
11 April Apr Wednesday $retDate.dayShortName
12 April Apr Thursday $retDate.dayShortName
13 April Apr Friday $retDate.dayShortName
14 April Apr Saturday $retDate.dayShortName
15 April Apr Sunday $retDate.dayShortName
16 April Apr Monday $retDate.dayShortName
17 April Apr Tuesday $retDate.dayShortName
08 April Apr Sunday $outDate.dayShortName
09 April Apr Monday $outDate.dayShortName
10 April Apr Tuesday $outDate.dayShortName
11 April Apr Wednesday $outDate.dayShortName
$293 Spirit Airlines
1523462280000 ORD » 1523486700000 BOS, 1 (407)
1523724300000 BOS » 1523734380000 ORD, 0 (168)
$291 Spirit Airlines
1523462280000 ORD » 1523486700000 BOS, 1 (407)
1523810700000 BOS » 1523820780000 ORD, 0 (168)
$242 Spirit Airlines
1523462280000 ORD » 1523486700000 BOS, 1 (407)
1523897100000 BOS » 1523907180000 ORD, 0 (168)
12 April Apr Thursday $outDate.dayShortName
$218 Spirit Airlines
1523557140000 ORD » 1523566020000 BOS, 0 (148)
1523724300000 BOS » 1523734380000 ORD, 0 (168)
$193 Unknown Airline
1523530800000 ORD » 1523539080000 BOS, 0 (138)
1523793600000 BOS » 1523804460000 ORD, 0 (181)
$167 Spirit Airlines
1523557140000 ORD » 1523566020000 BOS, 0 (148)
1523897100000 BOS » 1523907180000 ORD, 0 (168)
13 April Apr Friday $outDate.dayShortName
$243 Spirit Airlines
1523643540000 ORD » 1523652420000 BOS, 0 (148)
1523724300000 BOS » 1523734380000 ORD, 0 (168)
$241 Spirit Airlines
1523643540000 ORD » 1523652420000 BOS, 0 (148)
1523810700000 BOS » 1523820780000 ORD, 0 (168)
$192 Spirit Airlines
1523643540000 ORD » 1523652420000 BOS, 0 (148)
1523897100000 BOS » 1523907180000 ORD, 0 (168)
14 April Apr Saturday $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: Las Vegas - Boston New York - Boston London - Boston Miami - Boston San Francisco - Boston See more routes

Airlines operating flights from Chicago to Boston

  • any
  • January 2018
  • February 2018
  • March 2018
  • April 2018
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • all
  • American Airlines
  • JetBlue
  • Southwest Airlines
  • United Airlines
JetBlue
outbound: Feb 9, 2018
JetBlue direct
return: Feb 12, 2018
JetBlue direct
Southwest Airlines
outbound: Feb 9, 2018
Southwest Airlines direct
return: Feb 12, 2018
Southwest Airlines direct
United Airlines
outbound: Feb 9, 2018
United Airlines direct
return: Feb 12, 2018
United Airlines direct
American Airlines
outbound: Feb 9, 2018
American Airlines direct
return: Feb 12, 2018
American Airlines direct

Travel tips for flights Chicago - Boston

Average flight duration: 2h40m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jan 16, 2018 10:02 PM, GMT-5
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jan 16, 2018 9:02 PM, GMT-6