Flights from Boston to Chicago

Our cheapest offers for flights from Boston to Chicago

Here you can compare cheap flights from Boston (BOS) to Chicago (CHI) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Chicago. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Boston
Chicago
Outbound
02/13/26
1 Stopover (JFK)
B60817, B61305
09h 48min
Return
02/26/26
direct
B61012
02h 25min
JetBlue Airways ?
$245
Best option
Boston
Chicago
Outbound
04/03/26
direct
B60311
02h 54min
Return
04/16/26
direct
B60312
02h 26min
JetBlue Airways ?
$263
Boston
Chicago
Outbound
02/13/26
1 Stopover (JFK)
B60817, B61305
09h 48min
Return
02/26/26
direct
B61012
02h 25min
JetBlue Airways ?
$251
Boston
Chicago
Outbound
04/03/26
direct
B60311
02h 54min
Return
04/16/26
direct
B60312
02h 26min
JetBlue Airways ?
$267
Boston
Chicago
Outbound
04/03/26
direct
AA1245
03h 00min
Return
04/16/26
direct
AA3325
02h 21min
American Airlines ?
$365
Boston
Chicago
Outbound
02/13/26
1 Stopover (FLL)
NK3060, NK3153
11h 30min
Return
02/26/26
1 Stopover (MCO)
NK1880, NK2403
10h 50min
Spirit Airlines
$407
Boston
Chicago
Outbound
02/13/26
direct
AA1328
03h 05min
Return
02/26/26
direct
AA3710
02h 20min
American Airlines ?
$421
Boston
Chicago
Outbound
04/03/26
1 Stopover (ATL)
F93511, F92291
25h 41min
Return
04/16/26
1 Stopover (VPS)
G41487, G43066
17h 11min
Frontier Airlines ?
$421
Boston
Chicago
Outbound
02/13/26
direct
UA0398
03h 05min
Return
02/26/26
1 Stopover (EWR)
UA1658, UA0375
04h 15min
United Airlines
$434
Boston
Chicago
Outbound
04/03/26
direct
AA1245
03h 00min
Return
04/16/26
direct
AA3325
02h 21min
American Airlines ?
$437
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

Favorite airline: Sun Country Airlines
Sun Country Airlines is the most popular airline for flights from Boston to Chicago.
Sun Country Airlines
30 %
American Airlines
19 %
United Airlines
16 %
Cheapest weekday: Friday
Choosing the right day of the week is worthwhile as prices of flights on this route are cheapest on Friday.
Direct flights are the cheapest connection
Direct flights on this route are $18.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
02h 59min
05h 45min
$ 199
$ 217
Favourite connection: via Minneapolis
Flights with a stopover in Minneapolis are the most popular connection for this route.
Route
bookings
1 stopover Minneapolis - St. Paul International Airport, MN
08h 25min, from $ 286
33 %
Direct flights
02h 59min, from $ 199
32 %
1 stopover Orlando International Airport, FL
10h 02min, from $ 298
13 %

Important flight information

Flight information: Boston - Chicago

Roundtrip from $ 244,85
Flight duration min. 02:45 / max. 06:55
Return flight duration min. 02:08/ max. 11:15
Distance 1371 km
Flights per week 162
Departure airport Airport Boston Logan International Airport, MA (BOS)
Arrival airport Airport Chicago-IL, all airports (CHI)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Chicago
Flight destinations with a similar price
Flight destinations with a similar price