Flights from Boston to Chicago

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Outbound flight: 11/14/23
13:00 BOS
14:54 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 11/28/23
17:57 CHI
21:11 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$130
Check
Outbound flight: 11/14/23
13:00 BOS
14:54 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 11/28/23
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$130
Check
Outbound flight: 11/14/23
09:59 BOS
11:48 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 11/28/23
14:00 CHI
17:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$130
Check
Outbound flight: 11/20/23
20:17 BOS
22:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 12/04/23
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$157
Check
Outbound flight: 11/20/23
20:17 BOS
22:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 12/04/23
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$157
Check
Outbound flight: 11/20/23
20:17 BOS
22:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 12/04/23
16:00 CHI
23:54 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
United Airlines
$162
Check
Outbound flight: 11/14/23
08:15 BOS
09:57 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 11/28/23
08:52 CHI
12:11 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$162
Check
Outbound flight: 11/14/23
19:30 BOS
23:42 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
United Airlines
Return flight: 11/28/23
17:57 CHI
21:11 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$172
Check
Outbound flight: 11/14/23
13:30 BOS
21:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
United Airlines
Return flight: 11/28/23
17:57 CHI
21:11 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$196
Check
Outbound flight: 11/14/23
13:30 BOS
21:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
United Airlines
Return flight: 11/28/23
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$196
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
If booked 5 weeks before travel, flights cost 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.