| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Boston Chicago | Outbound 07/02/25 direct AA3324 02h 54min | Return 07/25/25 direct B61012 02h 35min |  American Airlines |  | ? | $106 found 3 days ago | |
| 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 08/28/25 direct AA3233 02h 59min | Return 09/19/25 direct AA2682 02h 44min | American Airlines | | ? | $111 | |
| 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 10/18/25 1 Stopover (FLL) NK0296, NK0866 09h 24min | Return 10/24/25 direct B61012 02h 30min |  Spirit Airlines | | ? | $135 | |
| Boston Chicago | Outbound 08/19/25 direct B60311 02h 55min | Return 09/02/25 direct AA2837 02h 24min | JetBlue Airways | | ? | $137 | |
| Boston Chicago | Outbound 09/19/25 direct B60311 02h 54min | Return 09/29/25 direct B61012 02h 30min | JetBlue Airways | | ? | $141 | |
| 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
- Spirit Airlines
- JetBlue Airways
- Frontier Airlines
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 | $105.32 |
|---|---|
| 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 $113
- Flight Boston - Los Angeles from $181
- Flight Boston - San Francisco from $226
- Flight Boston - Miami from $133
- Flight Boston - Orlando from $135
- Flight Boston - Fort Myers from $182
- Flight Boston - Washington-DC from $116
- Flight Boston - Dallas from $158
- Flight Boston - New York from $136
- Flight Boston - Seattle-Tacoma from $229
Alternative flights to Chicago
- Flight New York - Chicago from $55
- Flight Los Angeles - Chicago from $182
- Flight Las Vegas - Chicago from $158
- Flight Washington-DC - Chicago from $105
- Flight Atlanta - Chicago from $66
- Flight Denver - Chicago from $134
- Flight Fort Myers - Chicago from $154
- Flight Tampa - Chicago from $124
- Flight San Francisco - Chicago from $220
- Flight Philadelphia - Chicago from $180
Flight destinations with a similar price
- Flight Chicago - Berlin from $578
- Flight Chicago - Frankfurt from $611
- Flight Chicago - Hannover from $644
- Flight Chicago - Amsterdam from $525
- Flight Chicago - Havana from $386
- Flight Chicago - Mexico City from $250
- Flight Chicago - Dusseldorf from $627
- Flight Chicago - Dublin from $464
- Flight Chicago - Munich from $608
- Flight Chicago - Hamburg from $592
Flight destinations with a similar price
- Flight Boston - New York from $113
- Flight Boston - Washington-DC from $116
- Flight Boston - Chicago O'Hare from $111
- Flight Boston - Washington DC from $116
- Flight Boston - Atlanta from $110
- Flight Boston - Charleston from $97
- Flight Boston - Newark from $113
- Flight Boston - Presque Isle from $108