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
04/21/25
1 Stopover (MCO)
NK1338, NK0568
12h 52min
Return
05/19/25
1 Stopover (ATL)
NK1195, NK3380
08h 30min
Spirit Airlines
$138
Best option
Boston
Chicago
Outbound
06/20/25
direct
B60311
02h 55min
Return
07/19/25
direct
B60312
02h 25min
JetBlue Airways ?
$220
Boston
Chicago
Outbound
04/21/25
1 Stopover (MCO)
NK0997, NK0568
11h 45min
Return
05/19/25
1 Stopover (ATL)
NK1195, NK3380
08h 30min
Spirit Airlines
$146
Boston
Chicago
Outbound
04/21/25
1 Stopover (MCO)
NK0997, NK0568
11h 45min
Return
05/19/25
1 Stopover (MCO)
F93044, F93348
07h 29min
Spirit Airlines ?
$173
Boston
Chicago
Outbound
04/12/25
direct
B60611
03h 08min
Return
04/27/25
1 Stopover (ATL)
F91596, F93512
28h 18min
JetBlue Airways ?
$199
found yesterday
Boston
Chicago
Outbound
04/12/25
1 Stopover (MCO)
NK0997, NK0568
11h 33min
Return
04/27/25
2 Stopovers (FLL, BWI)
NK0267, NK0845, NK0612
34h 34min
Spirit Airlines
$236
found yesterday
Boston
Chicago
Outbound
04/12/25
1 Stopover (MCO)
NK0997, NK0568
11h 33min
Return
04/27/25
2 Stopovers (MCO, ATL)
NK0573, NK0211, NK0214
25h 35min
Spirit Airlines ?
$240
found yesterday
Boston
Chicago
Outbound
06/10/25
direct
B60811
03h 07min
Return
06/29/25
1 Stopover (JFK)
B60406, B60418
04h 51min
JetBlue Airways ?
$243
Boston
Chicago
Outbound
06/10/25
direct
UA2229
02h 52min
Return
06/29/25
direct
UA2067
02h 23min
United Airlines ?
$245
Boston
Chicago
Outbound
06/20/25
direct
AA3324
02h 55min
Return
07/19/25
direct
UA1495
02h 32min
American Airlines ?
$246
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 $137.88
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