Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Boston Chicago | Outbound 10/09/25 1 Stopover (BNA) NK2301, NK1765 28h 07min | Return 11/05/25 1 Stopover (FLL) NK0411, NK2304 12h 51min | | ![]() | $183 | ||
Best option Boston Chicago | Outbound 09/26/25 direct UA2229 02h 48min | Return 09/28/25 direct UA1779 02h 30min | | ![]() | ? | $192 | |
Boston Chicago | Outbound 09/26/25 direct B60811 03h 15min | Return 09/28/25 direct UA1779 02h 30min | | ![]() | ? | $203 | |
Boston Chicago | Outbound 09/26/25 1 Stopover (FLL) NK0448, NK1225 12h 29min | Return 09/28/25 1 Stopover (FLL) NK1380, NK0449 11h 00min | | ![]() | $205 | ||
Boston Chicago | Outbound 10/09/25 1 Stopover (FLL) NK0448, NK1777 10h 45min | Return 11/05/25 direct B61012 02h 32min | | ![]() | ? | $206 | |
Boston Chicago | Outbound 09/26/25 direct B60811 03h 15min | Return 09/28/25 1 Stopover (FLL) NK1380, NK0449 11h 00min | | ![]() | ? | $206 | |
Boston Chicago | Outbound 09/26/25 direct UA1015 02h 55min | Return 09/28/25 direct UA1779 02h 30min | | ![]() | ? | $212 | |
Boston Chicago | Outbound 10/09/25 1 Stopover (FLL) NK0448, NK1225 13h 25min | Return 11/05/25 direct B61012 02h 32min | | ![]() | ? | $221 | |
Boston Chicago | Outbound 09/26/25 direct UA1015 02h 55min | Return 09/28/25 direct UA1779 02h 30min | | ![]() | $240 | ||
Boston Chicago | Outbound 10/09/25 1 Stopover (LGA) AA4424, AA3165 05h 09min | Return 11/05/25 direct AA3710 02h 25min | | ![]() | ? | $269 |
Stops
- Direct flight
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 | $ 182,84 |
---|---|
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 $ 152
- Flight Boston - Los Angeles from $ 210
- Flight Boston - San Francisco from $ 207
- Flight Boston - Miami from $ 130
- Flight Boston - Orlando from $ 145
- Flight Boston - Fort Myers from $ 122
- Flight Boston - Washington-DC from $ 164
- Flight Boston - Dallas from $ 202
- Flight Boston - New York from $ 152
- Flight Boston - Seattle-Tacoma from $ 262
Alternative flights to Chicago
- Flight New York - Chicago from $ 104
- Flight Washington-DC - Chicago from $ 144
- Flight Atlanta - Chicago from $ 104
- Flight Denver - Chicago from $ 143
- Flight Tampa - Chicago from $ 112
- Flight San Francisco - Chicago from $ 244
- Flight Phoenix - Sky Harbor - Chicago from $ 142
- Flight Dallas - Chicago from $ 151
- Flight Nashville - Chicago from $ 134
- Flight Birmingham-Alabama - Chicago from $ 252
Flight destinations with a similar price
- Flight Chicago - Vienna from $ 746
- Flight Chicago - Toronto from $ 197
- Flight Chicago - Santiago de Chile from $ 682
- Flight Chicago - London from $ 509
- Flight Chicago - San Jose, Costa Rica from $ 710
- Flight Chicago - Havana from $ 586
- Flight Chicago - Berlin from $ 750
- Flight Chicago - Frankfurt from $ 584
- Flight Chicago - Hannover from $ 878
- Flight Chicago - Dusseldorf from $ 710
Flight destinations with a similar price
- Flight Boston - Chicago O'Hare from $ 183
- Flight Boston - Phoenix - Sky Harbor from $ 184
- Flight Boston - New York from $ 201
- Flight Boston - Pittsburgh from $ 179
- Flight Boston - Houston - George Bush from $ 175
- Flight Boston - Knoxville from $ 201
- Flight Boston - Houston - Metro from $ 175
- Flight Boston - Toronto from $ 196
- Flight Boston - Toronto from $ 196
- Flight Boston - Baltimore from $ 192