| 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 |  American Airlines |  | ? | $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 |  Spirit Airlines |  | $225 | ||
| Boston Chicago | Outbound 10/09/25 1 Stopover (BNA) NK2301, NK1765 28h 07min | Return 11/05/25 1 Stopover (FLL) NK0411, NK2304 12h 51min | Spirit Airlines |  | $183 | ||
| Boston Chicago | Outbound 11/09/25 direct UA1314 03h 00min | Return 12/07/25 direct UA1693 02h 20min |  United Airlines |  | ? | $195 | |
| Boston Chicago | Outbound 11/09/25 direct UA1314 03h 00min | Return 12/07/25 direct UA1989 02h 28min | United Airlines |  | $205 | ||
| Boston Chicago | Outbound 10/09/25 1 Stopover (FLL) NK0448, NK1777 10h 45min | Return 11/05/25 direct B61012 02h 32min | Spirit Airlines |  | ? | $206 | |
| Boston Chicago | Outbound 11/09/25 direct B60311 03h 05min | Return 12/07/25 direct B61012 02h 16min |  JetBlue Airways | | ? | $207 | |
| Boston Chicago | Outbound 10/09/25 1 Stopover (FLL) NK0448, NK1225 13h 25min | Return 11/05/25 direct B61012 02h 32min | Spirit Airlines | | ? | $221 | |
| Boston Chicago | Outbound 02/13/26 1 Stopover (JFK) B60817, B61305 09h 48min | Return 02/26/26 direct B61012 02h 25min | JetBlue Airways | | ? | $245 | |
| Boston Chicago | Outbound 02/13/26 1 Stopover (JFK) B60817, B61305 09h 48min | Return 02/26/26 direct B61012 02h 25min | JetBlue Airways | | ? | $251 |
Stops
- Direct flight
Airline
- American Airlines
- United Airlines
- Spirit Airlines
- JetBlue Airways
- 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 Los Angeles - Chicago from 194 $
- Flight Washington-DC - Chicago from 189 $
- Flight Atlanta - Chicago from 61 $
- Flight Denver - Chicago from 135 $
- Flight Tampa - Chicago from 112 $
- Flight San Francisco - Chicago from 202 $
- Flight Phoenix - Sky Harbor - Chicago from 197 $
- Flight Dallas - Chicago from 115 $
- Flight Nashville - Chicago from 117 $
Flight destinations with a similar price
- Flight Chicago - Vienna from 496 $
- Flight Chicago - Toronto from 283 $
- Flight Chicago - Santiago de Chile from 654 $
- Flight Chicago - London from 438 $
- 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 $