| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Chicago Boston | Outbound 03/28/26 direct UA1182 02h 20min | Return 04/25/26 direct AA1040 03h 15min |  United Airlines |  | ? | $193 | |
| Chicago Boston | Outbound 03/28/26 2 Stopovers (EWR, MCO) NK0107, NK1066, NK0272 21h 28min | Return 04/25/26 1 Stopover (FLL) NK1740, NK0001 19h 01min |  Spirit Airlines |  | $355 | ||
| Chicago Boston | Outbound 05/16/26 1 Stopover (MCO) NK1605, NK0272 06h 25min | Return 05/29/26 1 Stopover (FLL) NK1740, NK2204 30h 47min | Spirit Airlines |  | $219 | ||
| Chicago Boston | Outbound 05/16/26 direct AA2278 02h 34min | Return 05/29/26 1 Stopover (EWR) UA1693, UA1206 05h 30min |  American Airlines | | ? | $236 | |
| Chicago Boston | Outbound 03/28/26 direct UA1182 02h 20min | Return 04/25/26 direct UA1349 03h 00min | United Airlines |  | ? | $255 | |
| Chicago Boston | Outbound 03/28/26 direct B60312 02h 24min | Return 04/25/26 direct B60811 03h 01min |  JetBlue Airways |  | ? | $270 | |
| Chicago Boston | Outbound 03/28/26 1 Stopover (ATL) F92198, F93512 17h 50min | Return 04/25/26 1 Stopover (ATL) F93085, F93397 17h 39min |  Frontier Airlines |  | ? | $287 | |
| Chicago Boston | Outbound 07/26/26 direct UA1186 02h 24min | Return 08/05/26 direct UA2631 02h 58min | United Airlines | | ? | $293 | |
| Chicago Boston | Outbound 05/16/26 1 Stopover (MCO) NK1605, NK0272 06h 25min | Return 05/29/26 direct B60811 02h 56min | Spirit Airlines | | ? | $300 | |
| Chicago Boston | Outbound 05/16/26 direct UA2331 02h 36min | Return 05/29/26 1 Stopover (EWR) UA1693, UA1206 05h 30min | United Airlines | | ? | $310 |
Stops
- Direct flight
Airline
- United Airlines
- Spirit Airlines
- American Airlines
- Delta Air Lines
- 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
| Roundtrip from | $ 192,83 |
|---|---|
| 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 $ 69
- Flight Chicago - Las Vegas from $ 127
- Flight Chicago - Los Angeles from $ 169
- Flight Chicago - Miami from $ 135
- Flight Chicago - San Francisco from $ 161
- Flight Chicago - Tampa from $ 165
- Flight Chicago - Denver from $ 145
- Flight Chicago - Orlando from $ 179
- Flight Chicago - New Orleans from $ 160
- Flight Chicago - Atlanta from $ 134
Alternative flights to Boston
- Flight New York - Boston from $ 192
- Flight New York - Boston from $ 192
- Flight Washington-DC - Boston from $ 178
- Flight Buffalo - Boston from $ 161
- Flight Austin - Boston from $ 185
- Flight Las Vegas - Boston from $ 152
- Flight Washington DC - Boston from $ 237
- Flight Fort Lauderdale - Boston from $ 100
- Flight Atlanta - Boston from $ 95
- Flight Chicago O'Hare - Boston from $ 193
Flight destinations with a similar price
- Flight Boston - Aruba from $ 343
- Flight Boston - Bermuda from $ 380
- Flight Boston - Paris - Charles de Gaulle from $ 558
- Flight Boston - Cancun from $ 352
- Flight Boston - Dublin from $ 414
- Flight Boston - Frankfurt from $ 319
- Flight Boston - Mexico City from $ 447
- Flight Boston - Munich from $ 732
- Flight Boston - Santo Domingo from $ 268
- Flight Boston - San Jose, Costa Rica from $ 326
Flight destinations with a similar price
- Flight Chicago - Orlando from $ 179
- Flight Chicago - Phoenix - Sky Harbor from $ 177
- Flight Chicago - St. Louis from $ 183
- Flight Chicago - Louisville from $ 203
- Flight Chicago - Appleton from $ 207
- Flight Chicago - Toronto from $ 207