| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Boston Chicago | Outbound 06/18/25 direct B60311 02h 55min | Return 07/15/25 1 Stopover (JFK) B60906, B60618 04h 53min |  JetBlue Airways |  | ? | $120 | |
| Best option Boston Chicago | Outbound 06/18/25 direct UA1414 02h 58min | Return 07/15/25 direct UA0721 02h 35min |  United Airlines |  | ? | $146 | |
| Boston Chicago | Outbound 06/18/25 direct AA0598 02h 52min | Return 07/15/25 1 Stopover (JFK) B60406, B60418 04h 51min |  American Airlines |  | ? | $131 | |
| Boston Chicago | Outbound 04/21/25 1 Stopover (MCO) NK1338, NK0568 12h 52min | Return 05/19/25 1 Stopover (ATL) NK1195, NK3380 08h 30min |  Spirit Airlines |  | $138 | ||
| Boston Chicago | Outbound 04/21/25 1 Stopover (MCO) NK0997, NK0568 11h 45min | Return 05/19/25 1 Stopover (ATL) NK1195, NK3380 08h 30min | Spirit Airlines |  | $146 | ||
| Boston Chicago | Outbound 06/18/25 direct UA1414 02h 58min | Return 07/15/25 direct UA1129 02h 27min | United Airlines |  | ? | $147 | |
| Boston Chicago | Outbound 04/21/25 1 Stopover (MCO) NK0997, NK0568 11h 45min | Return 05/19/25 1 Stopover (MCO) F93044, F93348 07h 29min | Spirit Airlines | | ? | $173 | |
| Boston Chicago | Outbound 04/12/25 direct B60611 03h 08min | Return 04/27/25 1 Stopover (ATL) F91596, F93512 28h 18min | JetBlue Airways | | ? | $199 | |
| Boston Chicago | Outbound 06/20/25 direct B60311 02h 55min | Return 07/19/25 direct B60312 02h 25min | JetBlue Airways | | ? | $220 | |
| Boston Chicago | Outbound 04/12/25 1 Stopover (MCO) NK0997, NK0568 11h 33min | Return 04/27/25 2 Stopovers (FLL, BWI) NK0267, NK0845, NK0612 34h 34min | Spirit Airlines | | $236 |
Airline
- United Airlines
- Spirit Airlines
- American 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 | 119,46 $ |
|---|---|
| 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 (ORD, MDW, RFD) (CHI) |
| Destination country | Flights to United States |
Alternative routes to United States
- Flight Boston - New York from 77 $
- Flight Boston - Los Angeles from 181 $
- Flight Boston - San Francisco from 235 $
- Flight Boston - Miami from 138 $
- Flight Boston - Orlando from 130 $
- Flight Boston - Fort Myers from 176 $
- Flight Boston - Washington-DC from 116 $
- Flight Boston - Dallas from 156 $
- Flight Boston - New York from 161 $
- Flight Boston - Seattle-Tacoma from 307 $
Alternative flights to Chicago
- Flight New York - Chicago from 55 $
- Flight Los Angeles - Chicago from 144 $
- Flight Las Vegas - Chicago from 97 $
- Flight Washington-DC - Chicago from 105 $
- Flight Atlanta - Chicago from 57 $
- Flight Denver - Chicago from 101 $
- Flight Fort Myers - Chicago from 172 $
- Flight Tampa - Chicago from 87 $
- Flight San Francisco - Chicago from 156 $
- Flight Philadelphia - Chicago from 248 $
Flight destinations with a similar price
- Flight Chicago - Montego Bay from 403 $
- Flight Chicago - Toronto from 189 $
- Flight Chicago - Delhi from 622 $
- Flight Chicago - Cancun from 266 $
- Flight Chicago - San Jose, Costa Rica from 310 $
- Flight Chicago - Mumbai from 632 $
- Flight Chicago - Guadalajara from 243 $
- Flight Chicago - Hyderabad from 709 $
- Flight Chicago - Morelia from 245 $
- Flight Chicago - Vienna from 562 $
Flight destinations with a similar price
- Flight Boston - Orlando from 130 $
- Flight Boston - Washington-DC from 116 $
- Flight Boston - Chicago O'Hare from 120 $
- Flight Boston - Fort Lauderdale from 126 $
- Flight Boston - Nashville from 118 $
- Flight Boston - Washington DC from 116 $
- Flight Boston - Philadelphia from 124 $
- Flight Boston - New York from 111 $
- Flight Boston - Charlotte from 131 $
- Flight Boston - Jacksonville, Florida from 117 $