Flight Routes from Boston to Chicago

Trip type

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
06/25/26
direct
B60311
02h 56min
Return
06/30/26
direct
B60312
02h 27min
JetBlue Airways
$209
Boston
Chicago
Please note: transfer for connecting flight
Outbound
06/25/26
1 Stopover (ATL)
F93511, F92291
09h 24min
Return
06/30/26
1 Stopover (YTZ)
PD2388, TS7356
05h 21min
Frontier Airlines
$642
Boston
Chicago
Outbound
06/25/26
direct
UA1015
03h 00min
Return
06/30/26
direct
B61012
02h 31min
United Airlines ?
$209
Boston
Chicago
Outbound
07/26/26
direct
B60311
02h 56min
Return
08/05/26
direct
B61012
02h 31min
JetBlue Airways ?
$234
Boston
Chicago
Outbound
07/26/26
direct
B60311
02h 56min
Return
08/05/26
1 Stopover (JFK)
B60906, B60618
06h 56min
JetBlue Airways ?
$256
Boston
Chicago
Outbound
06/25/26
direct
UA2631
02h 58min
Return
06/30/26
direct
UA2466
02h 35min
United Airlines
$262
Boston
Chicago
Outbound
07/26/26
1 Stopover (ATL)
F93085, F92779
26h 00min
Return
08/05/26
1 Stopover (ATL)
F92292, F93086
14h 57min
Frontier Airlines ?
$377
Boston
Chicago
Outbound
06/25/26
1 Stopover (MSP)
SY0252, SY0261
09h 04min
Return
06/30/26
direct
UA1032
02h 36min
Sun Country Airlines ?
$385
Boston
Chicago
Outbound
06/25/26
direct
AA1554
03h 24min
Return
06/30/26
direct
AA3107
02h 34min
American Airlines ?
$410
Boston
Chicago
Outbound
07/26/26
1 Stopover (MSP)
SY0254, SY0261
08h 04min
Return
08/05/26
1 Stopover (MCO)
NK0392, NK0272
09h 52min
Sun Country Airlines
$413
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 $ 208,89
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