| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Chicago Boston | Outbound 12/01/25 2 Stopovers (MCO, DTW) NK0703, NK0750, NK2328 26h 51min | Return - |  Spirit Airlines |  | $137 | ||
| Best option Chicago Boston | Outbound 02/13/26 direct AA1033 02h 24min | Return 02/26/26 direct B60811 02h 52min |  American Airlines |  | ? | $143 | |
| Chicago Boston | Outbound 12/02/25 1 Stopover (JFK) B62106, B62918 05h 16min | Return 12/15/25 direct AA3691 03h 15min |  JetBlue Airways | | ? | $156 | |
| Chicago Boston | Outbound 12/02/25 1 Stopover (JFK) B62106, B62918 05h 16min | Return 12/15/25 direct B60811 03h 14min | JetBlue Airways |  | ? | $160 | |
| Chicago Boston | Outbound 12/02/25 1 Stopover (FLL) NK2413, NK0850 12h 41min | Return 12/15/25 1 Stopover (ATL) F93511, F91441 07h 04min | Spirit Airlines |  | $176 | ||
| Chicago Boston | Outbound 12/02/25 1 Stopover (FLL) NK2413, NK0850 12h 41min | Return 12/15/25 1 Stopover (ATL) F93511, F91441 07h 04min | Spirit Airlines | | $177 | ||
| Chicago Boston | Outbound 02/13/26 direct UA1989 02h 28min | Return 02/26/26 direct UA0398 03h 05min |  United Airlines |  | ? | $211 | |
| Chicago Boston | Outbound 12/02/25 direct AA1927 02h 24min | Return 12/15/25 direct AA2500 03h 13min | American Airlines |  | ? | $216 | |
| Chicago Boston | Outbound 02/13/26 direct B61012 02h 25min | Return 02/26/26 direct B60811 02h 52min | JetBlue Airways | | ? | $217 | |
| Chicago Boston | Outbound 12/02/25 direct AA0469 02h 22min | Return 12/15/25 direct AA2500 03h 13min | American Airlines | | ? | $230 |
Stops
- Direct flight
Airline
- American Airlines
- United Airlines
- Spirit Airlines
- JetBlue Airways
- Frontier Airlines
Tips and tricks to help you find cheap flights from Chicago to Boston
Favorite airline: Spirit Airlines
Flight tickets on the route Chicago – Boston are most frequently booked with Spirit Airlines.
Spirit Airlines
33 %
United Airlines
20 %
Delta
15 %
Direct flights are more expensive
On this route, direct flights are $13.00 more expensive than flights with a stopover.
non stop flight
1 stop
02h 30min
09h 23min
$ 160
$ 147
The favorite connection is non-stop
Flights from Chicago to Boston are most often booked as a direct flight.
Route
bookings
Direct flights
02h 30min, from $ 160
44 %
1 stopover Orlando International Airport, FL
09h 23min, from $ 147
15 %
1 stopover Minneapolis - St. Paul International Airport, MN
13h 44min, from $ 335
12 %
Important flight information
Flight information: Chicago - Boston
| Cheapest outbound flight from | $ 136,90 |
|---|---|
| Roundtrip from | $ 142,61 |
| Flight duration | min. 02:08 / max. 11:15 |
| Return flight duration | min. 02:45/ max. 06:55 |
| Distance | 1371 km |
| Flights per week | 153 |
| Departure airport | Airport Chicago-IL, all airports (CHI) |
| Arrival airport | Airport Boston Logan International Airport, MA (BOS) |
| Destination country | Flights to United States |
Alternative routes to United States
- Flight Chicago - New York from $ 67
- Flight Chicago - Las Vegas from $ 166
- Flight Chicago - Los Angeles from $ 143
- Flight Chicago - Miami from $ 141
- Flight Chicago - San Francisco from $ 339
- Flight Chicago - Tampa from $ 278
- Flight Chicago - Denver from $ 230
- Flight Chicago - Orlando from $ 250
- Flight Chicago - New Orleans from $ 251
- Flight Chicago - Atlanta from $ 230
Alternative flights to Boston
- Flight New York - Boston from $ 177
- Flight New York - Boston from $ 177
- Flight Washington-DC - Boston from $ 172
- Flight Orlando - Boston from $ 287
- Flight Buffalo - Boston from $ 229
- Flight Las Vegas - Boston from $ 146
- Flight Austin - Boston from $ 214
- Flight Fort Lauderdale - Boston from $ 119
- Flight Atlanta - Boston from $ 149
- Flight Chicago O'Hare - Boston from $ 137
Flight destinations with a similar price
- Flight Boston - Amsterdam from $ 457
- Flight Boston - Aruba from $ 655
- Flight Boston - Bermuda from $ 637
- Flight Boston - Paris - Charles de Gaulle from $ 548
- Flight Boston - Cancun from $ 323
- Flight Boston - Dublin from $ 338
- Flight Boston - Rome-Fiumicino from $ 447
- Flight Boston - Frankfurt from $ 373
- Flight Boston - London Heathrow from $ 477
- Flight Boston - Mexico City from $ 621
Flight destinations with a similar price
- Flight Chicago - Los Angeles from $ 143
- Flight Chicago - Miami from $ 141
- Flight Chicago - Owensboro from $ 138