Flights from Boston to Chicago

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Outbound flight: 05/10/22
12:31 BOS
14:20 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
Return flight: 05/24/22
22:00 CHI
01:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
$117
Check
Outbound flight: 05/10/22
15:46 BOS
17:45 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
Return flight: 05/24/22
14:55 CHI
18:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
$117
Check
Outbound flight: 05/10/22
14:09 BOS
16:00 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 05/24/22
06:55 CHI
10:10 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$126
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Outbound flight: 05/10/22
16:05 BOS
19:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
Return flight: 05/24/22
11:45 CHI
15:13 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$131
Check
Outbound flight: 05/24/22
19:38 BOS
21:25 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 06/07/22
06:52 CHI
13:00 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
$132
Check
Outbound flight: 05/10/22
10:00 BOS
11:48 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 05/24/22
19:59 CHI
23:33 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
$134
Check
Outbound flight: 05/24/22
12:55 BOS
16:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
Return flight: 06/07/22
18:25 CHI
23:26 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
$137
Check
Outbound flight: 05/24/22
20:25 BOS
22:21 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 06/07/22
18:55 CHI
00:50 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$138
Check
Outbound flight: 05/24/22
17:00 BOS
19:03 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 06/07/22
07:30 CHI
14:11 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$138
Check
Outbound flight: 05/24/22
20:25 BOS
22:21 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 06/07/22
18:55 CHI
00:50 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$138
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
Our tip: book flights on this route 5 weeks before departure and 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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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.