Flights from Boston to Chicago

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Outbound flight: 09/10/22
11:00 BOS
16:46 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
United Airlines
Return flight: 09/24/22
07:15 CHI
14:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
United Airlines
$143
Check
Outbound flight: 09/10/22
19:35 BOS
23:12 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
United Airlines
Return flight: 09/24/22
07:15 CHI
14:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
United Airlines
$143
Check
Outbound flight: 09/10/22
13:05 BOS
16:18 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
Return flight: 09/24/22
09:10 CHI
15:01 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$143
Check
Outbound flight: 09/10/22
09:05 BOS
12:38 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
Return flight: 09/24/22
09:10 CHI
15:01 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$143
Check
Outbound flight: 09/10/22
13:05 BOS
16:18 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
Return flight: 09/24/22
09:10 CHI
15:01 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$143
Check
Outbound flight: 09/10/22
11:00 BOS
16:46 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
United Airlines
Return flight: 09/24/22
07:15 CHI
14:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
United Airlines
$143
Check
Outbound flight: 09/10/22
19:35 BOS
23:12 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
United Airlines
Return flight: 09/24/22
07:15 CHI
14:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
United Airlines
$143
Check
Outbound flight: 09/10/22
05:30 BOS
09:31 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
Return flight: 09/24/22
13:00 CHI
16:33 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
$144
Check
Outbound flight: 09/10/22
09:05 BOS
12:32 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
Return flight: 09/24/22
16:45 CHI
20:28 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
$144
Check
Outbound flight: 09/10/22
10:00 BOS
11:48 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
Return flight: 09/24/22
13:00 CHI
16:33 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
$145
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 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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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.