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

Find cheap airline tickets from Boston to Chicago by date

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  • price
  • month of departure
  • month of return
$284
Spirit Airlines outward: Jun 23, 2023
11:35p BOS » 11:15p ORD
Spirit Airlines 1 stop (23h40m)
Unknown Company inbound: Jun 27, 2023
12:10a ORD » 3:02p BOS
Unknown Company 1 stop (14h52m)
$296
Spirit Airlines outward: Jun 16, 2023
11:35p BOS » 6:33p ORD
Spirit Airlines 1 stop (18h58m)
Unknown Company inbound: Jun 18, 2023
12:45p MDW » 7:08p BOS
Unknown Company 1 stop (6h23m)
$312
Frontier Airlines outward: Oct 6, 2023
5:44p BOS » 7:15p MDW
Frontier Airlines 1 stop (25h31m)
United Airlines inbound: Oct 10, 2023
4:18a ORD » 6:45a BOS
United Airlines direct (2h27m)
$2,795
Unknown Company outward: May 25, 2024
2:50a BOS » 2:45a ORD
Unknown Company 4 stops (47h55m)
Unknown Company inbound: May 27, 2024
9:40p ORD » 11:30p BOS
Unknown Company 3 stops (25h50m)
$3,036
Unknown Company outward: May 25, 2024
12:20a BOS » 3:00a ORD
Unknown Company 3 stops (26h40m)
Unknown Company inbound: May 28, 2024
2:10a ORD » 1:50a BOS
Unknown Company 4 stops (47h40m)
$4,159
Unknown Company outward: May 25, 2024
3:15a BOS » 2:45a ORD
Unknown Company 4 stops (47h30m)
Unknown Company inbound: May 27, 2024
9:40p ORD » 11:50p BOS
Unknown Company 3 stops (26h10m)
$4,556
Unknown Company outward: May 25, 2024
12:20a BOS » 3:00a ORD
Unknown Company 3 stops (26h40m)
Unknown Company inbound: May 27, 2024
10:45p ORD » 2:05a BOS
Unknown Company 3 stops (27h20m)
Return
Departure
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Airlines operating flights from Boston to Chicago

  • any
  • June 2023
  • July 2023
  • August 2023
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  • October 2023
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  • December 2023
  • January 2024
  • February 2024
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  • all
  • American Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jun 16, 2023
Spirit Airlines 1 stop
return: Jun 18, 2023
Frontier Airlines 1 stop
United Airlines
outbound: Oct 6, 2023
United Airlines direct
return: Oct 9, 2023
United Airlines direct
American Airlines
outbound: Jun 23, 2023
American Airlines direct
return: Jun 26, 2023
Delta Air Lines 1 stop

Travel tips for flights Boston - Chicago

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 8, 2023 8:23 PM, GMT-5
  • Weather:
  • min. 58ºF, max. 78ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Boston Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jun 8, 2023 9:23 PM, GMT-4
  • Weather:
  • min. 52ºF, max. 62ºF