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Find cheap airline tickets from Chicago to Boston by date

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$249
Unknown Company outward: Jul 27, 2023
12:45p MDW » 7:08p BOS
Unknown Company 1 stop (6h23m)
Unknown Company inbound: Jul 31, 2023
5:20p BOS » 4:40p MDW
Unknown Company 1 stop (23h20m)
Verify
15 days ago
$249
Unknown Company outward: Jul 27, 2023
12:45p MDW » 7:08p BOS
Unknown Company 1 stop (6h23m)
Unknown Company inbound: Jul 31, 2023
5:20p BOS » 4:40p MDW
Unknown Company 1 stop (23h20m)
Verify
15 days ago
$277
JetBlue outward: Jul 27, 2023
4:43p ORD » 9:03p BOS
JetBlue 1 stop (4h20m)
American Airlines inbound: Jul 31, 2023
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)
Verify
23 days ago
$292
Unknown Company outward: Jul 27, 2023
12:45p MDW » 7:08p BOS
Unknown Company 1 stop (6h23m)
American Airlines inbound: Jul 31, 2023
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)
Verify
21 days ago
$292
Unknown Company outward: Jul 27, 2023
12:45p MDW » 7:08p BOS
Unknown Company 1 stop (6h23m)
American Airlines inbound: Jul 31, 2023
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)
Verify
21 days ago
$298
Sun Country outward: Jul 28, 2023
3:15a ORD » 3:31p BOS
Sun Country 1 stop (12h16m)
Spirit Airlines inbound: Aug 1, 2023
2:25a BOS » 4:45p ORD
Spirit Airlines 1 stop (14h20m)
Verify
18 days ago
Return
Departure
Availability of fares is not guaranteed for offers found in the last 7 days.
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
  • June 2023
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  • American Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jul 27, 2023
Spirit Airlines 1 stop
return: Jul 31, 2023
Spirit Airlines 1 stop
$280 Verify
21 days ago
United Airlines
outbound: Jul 27, 2023
United Airlines direct
return: Jul 31, 2023
United Airlines direct
$322 Verify
15 days ago
American Airlines
outbound: Jul 27, 2023
American Airlines 1 stop
return: Jul 31, 2023
American Airlines direct
$389 Verify
21 days ago
Airline tickets Chicago - Boston found in the last 30 days.

Travel tips for flights Chicago - Boston

Average flight duration: 2h52m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Boston Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jun 27, 2023 4:54 AM, GMT-4
  • Weather:
  • min. 67ºF, max. 81ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 27, 2023 3:54 AM, GMT-5
  • Weather:
  • min. 62ºF, max. 77ºF
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