Flights from Boston to Chicago

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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
03/02/25
direct
UA1414
03h 04min
Return
03/07/25
direct
UA1495
02h 20min
United Airlines ?
$241
Boston
Chicago
Outbound
03/02/25
direct
AA1239
03h 14min
Return
03/07/25
direct
AA3703
02h 29min
American Airlines ?
$250
Boston
Chicago
Outbound
03/02/25
direct
AA1239
03h 14min
Return
03/07/25
direct
AA3296
02h 21min
American Airlines ?
$255
Boston
Chicago
Outbound
03/02/25
1 Stopover (EWR)
UA0570, UA1525
05h 38min
Return
03/07/25
direct
UA1495
02h 20min
United Airlines
$291
Boston
Chicago
Outbound
03/02/25
direct
AA1239
03h 14min
Return
03/07/25
direct
AA3703
02h 29min
American Airlines ?
$319
Boston
Chicago
Outbound
03/02/25
direct
UA1732
03h 02min
Return
03/07/25
direct
UA1495
02h 20min
United Airlines
$346
Boston
Chicago
Outbound
03/02/25
1 Stopover (ATL)
F93511, F92779
15h 49min
Return
03/07/25
2 Stopovers (ATL, ORD)
F92144, UA1046, UA1495
13h 57min
Frontier Airlines ?
$400
Boston
Chicago
Outbound
03/02/25
1 Stopover (FLL)
NK2887, NK0003
09h 31min
Return
03/07/25
1 Stopover (FLL)
NK0001, NK0616
07h 19min
Spirit Airlines
$467
Boston
Chicago
Outbound
03/02/25
1 Stopover (FLL)
NK0637, NK0003
10h 50min
Return
03/07/25
1 Stopover (FLL)
NK0001, NK0616
07h 19min
Spirit Airlines
$475
Boston
Chicago
Outbound
03/02/25
1 Stopover (FLL)
NK0637, NK0003
10h 50min
Return
03/07/25
1 Stopover (FLL)
NK0001, NK0616
07h 19min
Spirit Airlines
$490
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 $ 240,64
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 (ORD, MDW, RFD) (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
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.