Flights from Boston to Chicago

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Outbound flight: 05/19/21
12:47 BOS
14:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
Return flight: 06/02/21
15:22 CHI
18:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
$72
Check
Outbound flight: 05/25/21
12:47 BOS
14:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
Return flight: 06/08/21
15:22 CHI
18:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
$84
Check
Outbound flight: 05/25/21
12:47 BOS
14:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
Return flight: 06/08/21
15:22 CHI
18:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
$84
Check
Outbound flight: 05/19/21
12:47 BOS
14:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
Return flight: 06/02/21
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$91
Check
Outbound flight: 05/19/21
09:10 BOS
11:17 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 06/02/21
15:22 CHI
18:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
$91
Check
Outbound flight: 05/19/21
12:47 BOS
14:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
Return flight: 06/02/21
14:29 CHI
21:53 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$92
Check
Outbound flight: 05/19/21
15:00 BOS
18:52 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
Return flight: 06/02/21
15:22 CHI
18:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
$92
Check
Outbound flight: 05/02/21
06:00 BOS
07:51 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 05/16/21
08:45 CHI
12:12 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$95
Check
Outbound flight: 05/25/21
20:18 BOS
22:23 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 06/08/21
15:22 CHI
18:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
$101
Check
Outbound flight: 05/25/21
20:18 BOS
22:23 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 06/08/21
15:22 CHI
18:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
$101
Check
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Boston to Chicago

Tip: book 5 weeks before departure
The best time to buy tickets is 5 weeks before the flight. Pay only $132.00.
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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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.