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 | | ![]() | ? | $130 | |
Boston Chicago | Outbound 11/09/25 1 Stopover (BNA) NK0774, NK0417 26h 34min | Return 12/07/25 1 Stopover (FLL) NK1932, NK2304 29h 41min | | ![]() | $225 | ||
Boston Chicago | Outbound 11/09/25 direct UA1314 03h 00min | Return 12/07/25 direct UA1693 02h 20min | | ![]() | ? | $195 | |
Boston Chicago | Outbound 11/09/25 direct UA1314 03h 00min | Return 12/07/25 direct UA1989 02h 28min | | ![]() | $205 | ||
Boston Chicago | Outbound 11/09/25 direct B60311 03h 05min | Return 12/07/25 direct B61012 02h 16min | | ![]() | ? | $207 | |
Boston Chicago | Outbound 02/13/26 1 Stopover (JFK) B60817, B61305 09h 48min | Return 02/26/26 direct B61012 02h 25min | | ![]() | ? | $245 | |
Boston Chicago | Outbound 02/13/26 1 Stopover (JFK) B60817, B61305 09h 48min | Return 02/26/26 direct B61012 02h 25min | | ![]() | ? | $251 | |
Boston Chicago | Outbound 11/09/25 direct UA1414 03h 00min | Return 12/07/25 1 Stopover (ATL) F91596, F93086 18h 34min | | ![]() | ? | $265 | |
Boston Chicago | Outbound 11/09/25 direct AA0488 03h 07min | Return 12/07/25 direct AA3710 02h 25min | | ![]() | ? | $370 | |
Boston Chicago | Outbound 02/13/26 direct AA1328 03h 05min | Return 02/26/26 direct AA3710 02h 20min | | ![]() | ? | $384 |
Stops
- Direct flight
Airline
- American Airlines
- United Airlines
- JetBlue Airways
- Spirit Airlines
- Frontier Airlines
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
- Flight Boston - New York from $ 142
- Flight Boston - Los Angeles from $ 260
- Flight Boston - San Francisco from $ 267
- Flight Boston - Miami from $ 98
- Flight Boston - Orlando from $ 133
- Flight Boston - Fort Myers from $ 180
- Flight Boston - Washington-DC from $ 152
- Flight Boston - Dallas from $ 202
- Flight Boston - New York from $ 142
- Flight Boston - Seattle-Tacoma from $ 215
Alternative flights to Chicago
- Flight New York - Chicago from $ 122
- Flight Washington-DC - Chicago from $ 189
- Flight Atlanta - Chicago from $ 61
- Flight Denver - Chicago from $ 135
- Flight Tampa - Chicago from $ 106
- Flight San Francisco - Chicago from $ 202
- Flight Phoenix - Sky Harbor - Chicago from $ 197
- Flight Dallas - Chicago from $ 115
- Flight Nashville - Chicago from $ 117
- Flight Birmingham-Alabama - Chicago from $ 201
Flight destinations with a similar price
- Flight Chicago - London from $ 438
- Flight Chicago - Vienna from $ 496
- Flight Chicago - Toronto from $ 283
- Flight Chicago - Santiago de Chile from $ 654
- Flight Chicago - San Jose, Costa Rica from $ 302
- Flight Chicago - Havana from $ 482
- Flight Chicago - Berlin from $ 447
- Flight Chicago - Frankfurt from $ 444
- Flight Chicago - Hannover from $ 575
- Flight Chicago - Dusseldorf from $ 531
Flight destinations with a similar price
- Flight Boston - New York from $ 142
- Flight Boston - Orlando from $ 133
- Flight Boston - New York from $ 142
- Flight Boston - Chicago O'Hare from $ 130
- Flight Boston - Fort Lauderdale from $ 123
- Flight Boston - Nashville from $ 134
- Flight Boston - Knoxville from $ 119