Flights 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
05/16/26
direct
AA2815
03h 17min
Return
05/29/26
direct
AA2968
02h 26min
American Airlines ?
$196
Boston
Chicago
Please note: transfer for connecting flight
Outbound
05/16/26
1 Stopover (FLL)
NK1740, NK0001
19h 01min
Return
05/29/26
2 Stopovers (EWR, MYR)
NK0107, NK1412, NK1413
23h 47min
Spirit Airlines
$246
Boston
Chicago
Outbound
04/03/26
direct
B60311
02h 54min
Return
04/16/26
direct
B60312
02h 26min
JetBlue Airways ?
$263
Boston
Chicago
Outbound
05/16/26
1 Stopover (ATL)
F93511, F93397
11h 04min
Return
05/29/26
1 Stopover (JFK)
B60906, B60618
05h 24min
Frontier Airlines ?
$264
Boston
Chicago
Outbound
04/03/26
direct
B60311
02h 54min
Return
04/16/26
direct
B60312
02h 26min
JetBlue Airways ?
$267
Boston
Chicago
Outbound
05/16/26
direct
UA2040
03h 00min
Return
05/29/26
direct
UA1800
02h 36min
United Airlines ?
$271
Boston
Chicago
Outbound
05/16/26
direct
AA2815
03h 17min
Return
05/29/26
direct
AA2303
02h 35min
American Airlines
$278
Boston
Chicago
Outbound
05/16/26
1 Stopover (ATL)
F93085, F92291
14h 31min
Return
05/29/26
1 Stopover (VPS)
G43109, G43100
11h 26min
Frontier Airlines ?
$297
Boston
Chicago
Outbound
03/28/26
1 Stopover (ATL)
F93511, F91441
23h 16min
Return
04/25/26
2 Stopovers (IAH, ATL)
F93135, F91404, F93512
51h 15min
Frontier Airlines ?
$332
Boston
Chicago
Outbound
05/16/26
direct
AA2815
03h 17min
Return
05/29/26
direct
AA3107
02h 29min
American Airlines ?
$336
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 $196.00
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