| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Boston Chicago | Outbound 09/23/25 direct B60811 02h 50min | Return 09/30/25 direct AA1485 02h 24min |  JetBlue Airways |  | ? | $93 | |
| Boston Chicago | Outbound 10/18/25 3 Stopovers (FLL, PIT, PGD) NK2887, NK0228, G41110, G42478 25h 35min | Return 11/17/25 1 Stopover (TYS) G41432, G41397 16h 31min |   Spirit Airlines, Allegiant Air |  | $264 | ||
| Boston Chicago | Outbound 09/23/25 direct B60811 02h 50min | Return 09/30/25 direct B61012 02h 30min | JetBlue Airways |  | ? | $99 | |
| Boston Chicago | Outbound 09/04/25 direct B60811 02h 50min | Return 09/28/25 direct AA3710 02h 24min | JetBlue Airways | | ? | $102 | |
| Boston Chicago | Outbound 09/23/25 direct B60811 02h 50min | Return 09/30/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | JetBlue Airways | | ? | $105 | |
| Boston Chicago | Outbound 09/23/25 1 Stopover (FLL) NK2887, NK0003 09h 44min | Return 09/30/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | Spirit Airlines |  | $109 | ||
| Boston Chicago | Outbound 09/23/25 1 Stopover (FLL) NK0296, NK1026 12h 27min | Return 09/30/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | Spirit Airlines |  | $111 | ||
| Boston Chicago | Outbound 09/23/25 1 Stopover (FLL) NK0296, NK1026 12h 27min | Return 09/30/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | Spirit Airlines | | $121 | ||
| Boston Chicago | Outbound 10/18/25 1 Stopover (FLL) NK0296, NK0866 09h 24min | Return 10/24/25 direct B61012 02h 30min | Spirit Airlines | | ? | $135 | |
| Boston Chicago | Outbound 09/23/25 direct AA1509 03h 05min | Return 09/30/25 direct AA2682 02h 44min |  American Airlines |  | ? | $165 |
Stops
- Direct flight
Airline
- United Airlines
- American Airlines
- Spirit Airlines
- Frontier 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 | 92,34 $ |
|---|---|
| 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 80 $
- Flight Boston - Los Angeles from 181 $
- Flight Boston - San Francisco from 203 $
- Flight Boston - Miami from 147 $
- Flight Boston - Orlando from 126 $
- Flight Boston - Fort Myers from 146 $
- Flight Boston - Washington-DC from 130 $
- Flight Boston - Dallas from 158 $
- Flight Boston - New York from 159 $
- Flight Boston - Seattle-Tacoma from 178 $
Alternative flights to Chicago
- Flight New York - Chicago from 93 $
- Flight Los Angeles - Chicago from 103 $
- Flight Las Vegas - Chicago from 143 $
- Flight Washington-DC - Chicago from 187 $
- Flight Atlanta - Chicago from 79 $
- Flight Denver - Chicago from 170 $
- Flight Fort Myers - Chicago from 141 $
- Flight Tampa - Chicago from 124 $
- Flight San Francisco - Chicago from 201 $
- Flight Philadelphia - Chicago from 162 $
Flight destinations with a similar price
- Flight Chicago - Berlin from 425 $
- Flight Chicago - Frankfurt from 456 $
- Flight Chicago - Hannover from 442 $
- Flight Chicago - Amsterdam from 353 $
- Flight Chicago - Havana from 386 $
- Flight Chicago - Mexico City from 246 $
- Flight Chicago - Dusseldorf from 454 $
- Flight Chicago - Dublin from 345 $
- Flight Chicago - Munich from 445 $
- Flight Chicago - Hamburg from 426 $
Flight destinations with a similar price
- Flight Boston - Chicago O'Hare from 93 $
- Flight Boston - Detroit from 85 $
- Flight Boston - Charleston from 97 $
- Flight Boston - Savannah from 97 $
- Flight Boston - Knoxville from 91 $
- Flight Boston - Baltimore from 92 $
- Flight Boston - Presque Isle from 101 $