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Flights from Boston to Chicago

Due to the effect of the current situation on air traffic, fewer offers are being submitted. Some offers might now no longer be available.
Outbound flight: 05/04/20
15:23 BOS
17:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$39
Offers unavailable
Outbound flight: 05/04/20
15:23 BOS
17:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$39
Offers unavailable
Outbound flight: 05/04/20
13:45 BOS
15:44 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$54
Offers unavailable
Outbound flight: 05/04/20
13:45 BOS
15:44 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$54
Offers unavailable
Outbound flight: 05/04/20
18:40 BOS
23:55 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
$55
Offers unavailable
Outbound flight: 05/04/20
05:30 BOS
07:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$56
Offers unavailable
Outbound flight: 05/04/20
05:30 BOS
07:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$56
Offers unavailable
Outbound flight: 05/04/20
17:46 BOS
19:48 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
$57
Offers unavailable
Outbound flight: 05/04/20
20:20 BOS
22:05 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
$57
Offers unavailable
Outbound flight: 05/04/20
20:20 BOS
22:05 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
$57
Offers unavailable
Outbound flight: 05/04/20
20:20 BOS
22:05 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
$57
Offers unavailable
Outbound flight: 05/04/20
20:20 BOS
22:05 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
$57
Offers unavailable
Outbound flight: 05/04/20
15:23 BOS
17:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$58
Offers unavailable
Outbound flight: 05/04/20
15:23 BOS
17:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$58
Offers unavailable
Outbound flight: 05/04/20
15:23 BOS
17:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$58
Offers unavailable
Outbound flight: 05/04/20
15:23 BOS
17:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$58
Offers unavailable
Outbound flight: 05/04/20
18:16 BOS
22:57 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$58
Offers unavailable
Outbound flight: 05/04/20
18:16 BOS
22:57 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$58
Offers unavailable
Outbound flight: 05/04/20
11:36 BOS
13:30 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
$59
Offers unavailable
Outbound flight: 05/04/20
15:23 BOS
17:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$59
Offers unavailable
Prices based on recent searches, subject to last-minute changes
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Flight booking tips

Tip: book 5 weeks before departure
The best time to find a cheap flight on this route is 5 weeks before travel. Save up to 47 %.
36 days before departure
Flight information Boston - Chicago
Alternative flight routes
Cheap direct flights
Flight details Boston - Chicago
  • Flight duration: min. 02:45 / max. 06:55
  • Distance: 1371 km
  • Flights per week: 162
  • Return flight duration: min. 02:08 / max. 11:15
Top Flight Routes
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