| 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 09/23/25 direct AA1509 03h 05min | Return 09/30/25 direct AA2682 02h 44min |  American Airlines |  | ? | $165 | |
| 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 |
Stops
- Direct flight
Airline
- United Airlines
- American Airlines
- Frontier Airlines
- Spirit 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 $18.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
02h 59min
05h 45min
199 US$
217 US$
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 US$
33 %
Direct flights
02h 59min, from 199 US$
32 %
1 stopover Orlando International Airport, FL
10h 02min, from 298 US$
13 %
Important flight information
Flight information: Boston - Chicago
| Roundtrip from | 92,34 US$ |
|---|---|
| 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 US$
- Flight Boston - Los Angeles from 181 US$
- Flight Boston - San Francisco from 203 US$
- Flight Boston - Miami from 147 US$
- Flight Boston - Orlando from 126 US$
- Flight Boston - Fort Myers from 146 US$
- Flight Boston - Washington-DC from 130 US$
- Flight Boston - Dallas from 160 US$
- Flight Boston - New York from 159 US$
- Flight Boston - Seattle-Tacoma from 178 US$
Alternative flights to Chicago
- Flight New York - Chicago from 93 US$
- Flight Los Angeles - Chicago from 103 US$
- Flight Las Vegas - Chicago from 143 US$
- Flight Washington-DC - Chicago from 187 US$
- Flight Atlanta - Chicago from 36 US$
- Flight Denver - Chicago from 170 US$
- Flight Fort Myers - Chicago from 141 US$
- Flight Tampa - Chicago from 162 US$
- Flight San Francisco - Chicago from 201 US$
- Flight Philadelphia - Chicago from 162 US$
Flight destinations with a similar price
- Flight Chicago - Berlin from 425 US$
- Flight Chicago - Frankfurt from 456 US$
- Flight Chicago - Hannover from 442 US$
- Flight Chicago - Amsterdam from 353 US$
- Flight Chicago - Havana from 390 US$
- Flight Chicago - Mexico City from 246 US$
- Flight Chicago - Dusseldorf from 454 US$
- Flight Chicago - Dublin from 345 US$
- Flight Chicago - Munich from 445 US$
- Flight Chicago - Hamburg from 426 US$
Flight destinations with a similar price
- Flight Boston - Chicago O'Hare from 93 US$
- Flight Boston - Knoxville from 91 US$
- Flight Boston - Baltimore from 92 US$
- Flight Boston - Presque Isle from 101 US$