Flights from Boston to Chicago

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12+
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under 2 years
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Outbound flight: 12/22/20
18:00 BOS
21:51 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
Return flight: 01/05/21
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$90
Check
Outbound flight: 03/11/21
09:00 BOS
10:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 03/25/21
06:00 CHI
09:16 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$105
Check
Outbound flight: 03/11/21
09:00 BOS
10:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 03/25/21
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$105
Check
Outbound flight: 03/11/21
07:00 BOS
08:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 03/25/21
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$105
Check
Outbound flight: 03/11/21
09:00 BOS
10:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 03/25/21
06:00 CHI
09:16 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$105
Check
Outbound flight: 03/11/21
09:00 BOS
10:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 03/25/21
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$105
Check
Outbound flight: 12/16/20
09:00 BOS
10:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 12/30/20
06:00 CHI
09:16 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$105
Check
Outbound flight: 12/16/20
13:00 BOS
14:44 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 12/30/20
17:57 CHI
21:11 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$105
Check
Outbound flight: 02/01/21
09:00 BOS
10:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 02/15/21
12:00 CHI
15:17 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$106
Check
Outbound flight: 02/01/21
09:00 BOS
10:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 02/15/21
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$106
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