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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • any
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • price
  • month of departure
  • month of return
$180
JetBlue outward: Dec 6, 2019
12:25p ORD » 2:41p BOS
JetBlue direct (2h16m)
JetBlue inbound: Dec 8, 2019
9:01p BOS » 12:02a ORD
JetBlue direct (3h01m)
$181
JetBlue outward: Dec 7, 2019
4:38a ORD » 6:58a BOS
JetBlue direct (2h20m)
JetBlue inbound: Dec 8, 2019
9:01p BOS » 12:02a ORD
JetBlue direct (3h01m)
$187
American Airlines outward: Dec 6, 2019
1:00p ORD » 3:15p BOS
American Airlines direct (2h15m)
United Airlines inbound: Dec 8, 2019
2:33p BOS » 5:25p ORD
United Airlines direct (2h52m)
$187
American Airlines outward: Dec 6, 2019
1:00p ORD » 3:15p BOS
American Airlines direct (2h15m)
United Airlines inbound: Dec 8, 2019
2:33p BOS » 5:25p ORD
United Airlines direct (2h52m)
$188
United Airlines outward: Dec 6, 2019
1:00p ORD » 3:15p BOS
United Airlines direct (2h15m)
United Airlines inbound: Dec 8, 2019
2:33p BOS » 5:25p ORD
United Airlines direct (2h52m)
$188
United Airlines outward: Dec 6, 2019
1:00p ORD » 3:15p BOS
United Airlines direct (2h15m)
United Airlines inbound: Dec 8, 2019
2:33p BOS » 5:25p ORD
United Airlines direct (2h52m)
$199
American Airlines outward: Dec 6, 2019
3:49p ORD » 9:33p BOS
American Airlines 1 stop (5h44m)
American Airlines inbound: Dec 8, 2019
7:30p BOS » 10:27p ORD
American Airlines direct (2h57m)
$199
JetBlue outward: Dec 7, 2019
4:38a ORD » 6:58a BOS
JetBlue direct (2h20m)
JetBlue inbound: Dec 8, 2019
9:01p BOS » 12:02a ORD
JetBlue direct (3h01m)
$200
Spirit Airlines outward: Dec 7, 2019
3:40a ORD » 2:57a BOS
Spirit Airlines 1 stop (23h17m)
Spirit Airlines inbound: Dec 8, 2019
1:30p BOS » 1:55p ORD
Spirit Airlines 1 stop (24h25m)
$214
JetBlue outward: Nov 26, 2019
12:01p ORD » 2:17p BOS
JetBlue direct (2h16m)
JetBlue inbound: Dec 29, 2019
12:30p BOS » 3:30p ORD
JetBlue direct (3h)
$236
JetBlue outward: Nov 26, 2019
4:38a ORD » 6:58a BOS
JetBlue direct (2h20m)
JetBlue inbound: Dec 3, 2019
4:51a BOS » 7:35a ORD
JetBlue direct (2h44m)
Return
Departure
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
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • all
  • JetBlue
  • Spirit Airlines
  • United Airlines
JetBlue
outbound: Jan 24, 2020
JetBlue direct
return: Jan 26, 2020
JetBlue direct
Spirit Airlines
outbound: Nov 25, 2019
Spirit Airlines 1 stop
return: Dec 2, 2019
Alaska Airlines 1 stop
United Airlines
outbound: Nov 26, 2019
United Airlines direct
return: Dec 29, 2019
United Airlines direct

Travel tips for flights Chicago - Boston

Average flight duration: 2h32m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Nov 17, 2019 12:11 AM, GMT-5
  • Weather:
  • min. 28ºF, max. 41ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Nov 16, 2019 11:11 PM, GMT-6
  • Weather:
  • min. 35ºF, max. 40ºF