| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Boston Chicago | Outbound 08/28/25 direct AA3233 02h 59min | Return 09/19/25 direct AA2682 02h 44min |  American Airlines |  | ? | $111 | |
| Boston Chicago | Outbound 09/19/25 1 Stopover (AVL) G40226, G40513 08h 44min | Return 09/29/25 1 Stopover (TYS) G43021, G41397 13h 27min |  Allegiant Air |  | $297 | ||
| Boston Chicago | Outbound 06/18/25 direct B60311 02h 55min | Return 07/15/25 1 Stopover (JFK) B60906, B60618 04h 53min |  JetBlue Airways |  | ? | $120 | |
| 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 08/19/25 direct B60311 02h 55min | Return 09/02/25 direct AA2837 02h 24min | JetBlue Airways | | ? | $137 | |
| 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 09/19/25 direct B60311 02h 54min | Return 09/29/25 direct B61012 02h 30min | JetBlue Airways | | ? | $141 | |
| 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 UA0721 02h 35min |  United Airlines |  | ? | $146 | |
| Boston Chicago | Outbound 06/18/25 direct UA1414 02h 58min | Return 07/15/25 direct UA1129 02h 27min | United Airlines |  | ? | $147 |
Stops
- Direct flight
Airline
- American Airlines
- United 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 | 110,69 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 (ORD, MDW, RFD) (CHI) |
| Destination country | Flights to United States |
Alternative routes to United States
- Flight Boston - New York from 77 US$
- Flight Boston - Los Angeles from 181 US$
- Flight Boston - San Francisco from 226 US$
- Flight Boston - Miami from 138 US$
- Flight Boston - Orlando from 130 US$
- Flight Boston - Fort Myers from 183 US$
- Flight Boston - Washington-DC from 116 US$
- Flight Boston - Dallas from 156 US$
- Flight Boston - New York from 136 US$
- Flight Boston - Seattle-Tacoma from 279 US$
Alternative flights to Chicago
- Flight New York - Chicago from 55 US$
- Flight Los Angeles - Chicago from 182 US$
- Flight Las Vegas - Chicago from 158 US$
- Flight Washington-DC - Chicago from 105 US$
- Flight Atlanta - Chicago from 57 US$
- Flight Denver - Chicago from 108 US$
- Flight Minneapolis - Chicago from 186 US$
- Flight Dallas - Chicago from 101 US$
- Flight Honolulu - Chicago from 650 US$
- Flight Fort Lauderdale - Chicago from 129 US$
Flight destinations with a similar price
- Flight Chicago - Istanbul from 769 US$
- Flight Chicago - Vienna from 562 US$
- Flight Chicago - London from 534 US$
- Flight Chicago - Toronto from 203 US$
- Flight Chicago - Santiago de Chile from 586 US$
- Flight Chicago - San Jose, Costa Rica from 302 US$
- Flight Chicago - Havana from 405 US$
- Flight Chicago - Berlin from 502 US$
- Flight Chicago - Frankfurt from 525 US$
- Flight Chicago - Hannover from 623 US$
Flight destinations with a similar price
- Flight Boston - Washington-DC from 116 US$
- Flight Boston - Chicago O'Hare from 111 US$
- Flight Boston - Fort Lauderdale from 120 US$
- Flight Boston - Nashville from 118 US$
- Flight Boston - Washington DC from 116 US$
- Flight Boston - Jacksonville, Florida from 117 US$
- Flight Boston - Raleigh-Durham from 110 US$