| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Boston Chicago | Outbound 11/03/25 direct B60811 02h 52min | Return 11/12/25 1 Stopover (FLL) NK0867, NK0616 08h 10min |  JetBlue Airways |  | ? | $156 | |
| Best option Boston Chicago | Outbound 11/03/25 direct UA1414 02h 50min | Return 11/12/25 direct UA0399 02h 27min |  United Airlines |  | ? | $185 | |
| Boston Chicago | Outbound 11/03/25 1 Stopover (ATL) F93511, F91595 06h 15min | Return 11/12/25 1 Stopover (FLL) NK0867, NK0616 08h 10min |  Frontier Airlines | | ? | $168 | |
| Boston Chicago | Outbound 11/03/25 1 Stopover (BNA) NK3921, NK2028 05h 44min | Return 11/12/25 1 Stopover (FLL) NK0867, NK0616 08h 10min |  Spirit Airlines |  | $170 | ||
| Boston Chicago | Outbound 10/10/25 1 Stopover (RDU) F93057, F93351 09h 36min | Return 11/04/25 direct B61012 02h 25min | Frontier Airlines | | ? | $171 | |
| Boston Chicago | Outbound 11/03/25 1 Stopover (RDU) F93057, F93351 15h 00min | Return 11/12/25 1 Stopover (ATL) NK1195, NK1208 10h 34min | Frontier Airlines |  | $173 | ||
| Boston Chicago | Outbound 11/03/25 1 Stopover (RDU) F93057, F93351 15h 00min | Return 11/12/25 1 Stopover (ATL) NK1195, NK1208 10h 34min | Frontier Airlines |  | $186 | ||
| Boston Chicago | Outbound 11/03/25 direct UA1414 02h 50min | Return 11/12/25 direct UA1989 02h 33min | United Airlines |  | ? | $193 | |
| Boston Chicago | Outbound 11/03/25 direct UA2229 02h 44min | Return 11/12/25 direct UA1677 02h 33min | United Airlines |  | $201 | ||
| Boston Chicago | Outbound 11/03/25 direct AA1443 02h 57min | Return 11/12/25 direct AA4650 02h 32min |  American Airlines |  | ? | $230 |
Stops
- Direct flight
Airline
- United Airlines
- Frontier Airlines
- American Airlines
- Sun Country Airlines
- JetBlue Airways
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 | 155,53 $ |
|---|---|
| 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 111 $
- Flight Boston - Los Angeles from 181 $
- Flight Boston - San Francisco from 221 $
- Flight Boston - Miami from 155 $
- Flight Boston - Orlando from 146 $
- Flight Boston - Fort Myers from 146 $
- Flight Boston - Washington-DC from 145 $
- Flight Boston - Dallas from 169 $
- Flight Boston - New York from 178 $
- Flight Boston - Seattle-Tacoma from 219 $
Alternative flights to Chicago
- Flight New York - Chicago from 99 $
- Flight Los Angeles - Chicago from 103 $
- Flight Las Vegas - Chicago from 143 $
- Flight Washington-DC - Chicago from 190 $
- Flight Atlanta - Chicago from 36 $
- Flight Denver - Chicago from 170 $
- Flight Fort Myers - Chicago from 141 $
- Flight Tampa - Chicago from 112 $
- Flight San Francisco - Chicago from 201 $
- Flight Philadelphia - Chicago from 175 $
Flight destinations with a similar price
- Flight Chicago - Vienna from 390 $
- Flight Chicago - Toronto from 138 $
- Flight Chicago - Santiago de Chile from 615 $
- Flight Chicago - London from 413 $
- Flight Chicago - San Jose, Costa Rica from 305 $
- Flight Chicago - Havana from 419 $
- Flight Chicago - Berlin from 425 $
- Flight Chicago - Frankfurt from 456 $
- Flight Chicago - Hannover from 442 $
- Flight Chicago - Dusseldorf from 454 $
Flight destinations with a similar price
- Flight Boston - Miami from 155 $
- Flight Boston - Orlando from 146 $
- Flight Boston - Fort Myers from 146 $
- Flight Boston - Washington-DC from 145 $
- Flight Boston - Dallas from 169 $
- Flight Boston - Chicago O'Hare from 156 $
- Flight Boston - Tampa from 146 $
- Flight Boston - Buffalo from 170 $
- Flight Boston - Washington DC from 145 $
- Flight Boston - Detroit from 156 $