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
Best option
Boston
Chicago
Outbound
11/09/25
direct
AA0488
03h 07min
Return
12/07/25
direct
DL2570
02h 27min
American Airlines ?
$130
Boston
Chicago
Please note: transfer for connecting flight
Outbound
11/09/25
1 Stopover (BNA)
NK0774, NK0417
26h 34min
Return
12/07/25
1 Stopover (FLL)
NK1932, NK2304
29h 41min
Spirit Airlines
$225
Boston
Chicago
Outbound
11/09/25
direct
UA1314
03h 00min
Return
12/07/25
direct
UA1693
02h 20min
United Airlines ?
$195
Boston
Chicago
Outbound
11/09/25
direct
UA1314
03h 00min
Return
12/07/25
direct
UA1989
02h 28min
United Airlines
$205
Boston
Chicago
Outbound
11/09/25
direct
B60311
03h 05min
Return
12/07/25
direct
B61012
02h 16min
JetBlue Airways ?
$207
Boston
Chicago
Outbound
02/13/26
1 Stopover (JFK)
B60817, B61305
09h 48min
Return
02/26/26
direct
B61012
02h 25min
JetBlue Airways ?
$245
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
11/09/25
direct
UA1414
03h 00min
Return
12/07/25
1 Stopover (ATL)
F91596, F93086
18h 34min
United Airlines ?
$265
Boston
Chicago
Outbound
11/09/25
direct
AA0488
03h 07min
Return
12/07/25
direct
AA3710
02h 25min
American Airlines ?
$370
Boston
Chicago
Outbound
02/13/26
direct
AA1328
03h 05min
Return
02/26/26
direct
AA3710
02h 20min
American Airlines ?
$384
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 $ 129,79
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