| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Boston Chicago | Outbound 05/16/26 direct AA2815 03h 17min | Return 05/29/26 direct AA2968 02h 26min |  American Airlines |  | ? | $196 | |
| Boston Chicago | Outbound 05/16/26 1 Stopover (FLL) NK1740, NK0001 19h 01min | Return 05/29/26 2 Stopovers (EWR, MYR) NK0107, NK1412, NK1413 23h 47min |  Spirit Airlines |  | $246 | ||
| Boston Chicago | Outbound 06/25/26 direct B60311 02h 56min | Return 06/30/26 direct B60312 02h 27min |  JetBlue Airways |  | $209 | ||
| Boston Chicago | Outbound 06/25/26 direct UA1015 03h 00min | Return 06/30/26 direct B61012 02h 31min |  United Airlines | | ? | $209 | |
| Boston Chicago | Outbound 07/26/26 direct B60311 02h 56min | Return 08/05/26 1 Stopover (JFK) B60906, B60618 06h 56min | JetBlue Airways |  | ? | $256 | |
| Boston Chicago | Outbound 06/25/26 direct UA2631 02h 58min | Return 06/30/26 direct UA2466 02h 35min | United Airlines |  | $262 | ||
| Boston Chicago | Outbound 05/16/26 1 Stopover (ATL) F93511, F93397 11h 04min | Return 05/29/26 1 Stopover (JFK) B60906, B60618 05h 24min |  Frontier Airlines | | ? | $264 | |
| Boston Chicago | Outbound 05/16/26 direct UA2040 03h 00min | Return 05/29/26 direct UA1800 02h 36min | United Airlines | | ? | $271 | |
| Boston Chicago | Outbound 05/16/26 direct AA2815 03h 17min | Return 05/29/26 direct AA2303 02h 35min | American Airlines |  | $278 | ||
| Boston Chicago | Outbound 05/16/26 1 Stopover (ATL) F93085, F92291 14h 31min | Return 05/29/26 1 Stopover (VPS) G43109, G43100 11h 26min | Frontier Airlines |  | ? | $297 |
Stops
- Direct flight
Airline
- United Airlines
- Sun Country Airlines
- Frontier Airlines
- American 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 | 196,00 $ |
|---|---|
| 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 174 $
- Flight Boston - Los Angeles from 256 $
- Flight Boston - San Francisco from 258 $
- Flight Boston - Miami from 210 $
- Flight Boston - Fort Myers from 209 $
- Flight Boston - Orlando from 119 $
- Flight Boston - Washington-DC from 181 $
- Flight Boston - Dallas from 211 $
- Flight Boston - New York from 185 $
- Flight Boston - Seattle-Tacoma from 299 $
Alternative flights to Chicago
- Flight New York - Chicago from 119 $
- Flight Los Angeles - Chicago from 220 $
- Flight Washington-DC - Chicago from 177 $
- Flight Atlanta - Chicago from 79 $
- Flight Denver - Chicago from 143 $
- Flight Philadelphia - Chicago from 215 $
- Flight Minneapolis - Chicago from 148 $
- Flight Phoenix - Sky Harbor - Chicago from 185 $
- Flight Dallas - Chicago from 131 $
- Flight Fort Lauderdale - Chicago from 144 $
Flight destinations with a similar price
- Flight Chicago - Mumbai from 713 $
- Flight Chicago - Lahore from 1.051 $
- Flight Chicago - Lagos from 1.132 $
- Flight Chicago - Guadalajara from 267 $
- Flight Chicago - Hyderabad from 816 $
- Flight Chicago - Istanbul from 901 $
- Flight Chicago - Santiago de Chile from 569 $
- Flight Chicago - San Jose, Costa Rica from 357 $
- Flight Chicago - San Juan (Puerto Rico) from 213 $
- Flight Chicago - Toronto from 219 $
Flight destinations with a similar price
- Flight Boston - Miami from 210 $
- Flight Boston - Fort Myers from 209 $
- Flight Boston - Washington-DC from 181 $
- Flight Boston - Dallas from 211 $
- Flight Boston - New York from 185 $
- Flight Boston - Chicago O'Hare from 196 $
- Flight Boston - Nashville from 199 $
- Flight Boston - Washington DC from 181 $
- Flight Boston - New York from 200 $
- Flight Boston - Houston - Metro from 202 $