Flights from Boston to Chicago

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Outbound flight: 01/30/21
10:20 BOS
12:04 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
$42
Check
Outbound flight: 01/30/21
10:20 BOS
12:04 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
$42
Check
Outbound flight: 01/30/21
10:40 BOS
12:30 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$50
Check
Outbound flight: 01/30/21
10:40 BOS
12:30 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$50
Check
Outbound flight: 01/30/21
08:53 BOS
10:50 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
$51
Check
Outbound flight: 01/30/21
08:53 BOS
10:50 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
$51
Check
Outbound flight: 01/30/21
06:05 BOS
09:45 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
$52
Check
Outbound flight: 01/30/21
06:05 BOS
09:45 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
$52
Check
Outbound flight: 01/30/21
08:40 BOS
16:23 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines
$58
Check
Outbound flight: 01/30/21
05:25 BOS
11:45 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Southwest Airlines
$60
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.