| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Chicago Boston | Outbound 06/25/26 direct B60312 02h 27min | Return 06/30/26 direct B60811 03h 05min |  JetBlue Airways |  | ? | $212 | |
| Chicago Boston | Outbound 07/26/26 1 Stopover (MSP) SY0262, SY0251 14h 59min | Return 08/05/26 2 Stopovers (MSP, IWD) SY0252, KG5111, KG3914 28h 07min |  Sun Country Airlines |  | $567 | ||
| Chicago Boston | Outbound 07/26/26 direct UA1186 02h 24min | Return 08/05/26 direct UA2631 02h 58min |  United Airlines | | ? | $293 | |
| Chicago Boston | Outbound 07/26/26 direct UA1779 02h 33min | Return 08/05/26 direct UA2631 02h 58min | United Airlines |  | ? | $295 | |
| Chicago Boston | Outbound 07/26/26 1 Stopover (MCO) NK0392, NK0272 09h 52min | Return 08/05/26 direct B60311 02h 56min |  Spirit Airlines |  | ? | $346 | |
| Chicago Boston | Outbound 07/26/26 direct UA1186 02h 24min | Return 08/05/26 1 Stopover (MIA) AA2980, F93629 30h 09min | United Airlines |  | ? | $383 | |
| Chicago Boston | Outbound 07/26/26 direct AA2303 02h 35min | Return 08/05/26 direct AA3324 02h 56min |  American Airlines |  | ? | $440 | |
| Chicago Boston | Outbound 06/25/26 1 Stopover (ATL) F92198, F93086 06h 30min | Return 06/30/26 1 Stopover (ATL) F93085, F91441 07h 29min |  Frontier Airlines |  | $504 | ||
| Chicago Boston | Outbound 06/25/26 1 Stopover (ATL) F91596, F93086 16h 32min | Return 06/30/26 1 Stopover (ATL) F93085, F93397 17h 37min | Frontier Airlines | | ? | $520 | |
| Chicago Boston | Outbound 06/25/26 1 Stopover (IAD) UA2437, UA0755 07h 06min | Return 06/30/26 direct UA2631 02h 58min | United Airlines | | $612 |
Stops
- Direct flight
Airline
- United Airlines
- Sun Country Airlines
- Frontier Airlines
- American Airlines
- Delta Air Lines
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 | $ 211,80 |
|---|---|
| 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 $ 184
- Flight Chicago - Las Vegas from $ 127
- Flight Chicago - Los Angeles from $ 169
- Flight Chicago - Miami from $ 160
- Flight Chicago - San Francisco from $ 161
- Flight Chicago - Tampa from $ 168
- Flight Chicago - Denver from $ 123
- Flight Chicago - Orlando from $ 179
- Flight Chicago - New Orleans from $ 170
- Flight Chicago - Washington-DC from $ 321
Alternative flights to Boston
- Flight New York - Boston from $ 213
- Flight New York - Boston from $ 213
- Flight Washington-DC - Boston from $ 211
- Flight Orlando - Boston from $ 238
- Flight Buffalo - Boston from $ 186
- Flight Las Vegas - Boston from $ 383
- Flight Austin - Boston from $ 184
- Flight Washington DC - Boston from $ 317
- Flight Fort Lauderdale - Boston from $ 123
- Flight Atlanta - Boston from $ 214
Flight destinations with a similar price
- Flight Boston - Guadalajara from $ 620
- Flight Boston - Beijing from $ 1.356
- Flight Boston - Rabat from $ 389
- Flight Boston - Papeete from $ 1.659
- Flight Boston - Beirut from $ 937
- Flight Boston - Toronto - City Centre from $ 237
- Flight Boston - Amman from $ 911
- Flight Boston - Sarajevo from $ 617
- Flight Boston - Manila from $ 1.134
- Flight Boston - Riyadh from $ 851
Flight destinations with a similar price
- Flight Chicago - St. Louis from $ 210
- Flight Chicago - Philadelphia from $ 215
- Flight Chicago - Louisville from $ 212
- Flight Chicago - Jacksonville, Florida from $ 219
- Flight Chicago - Appleton from $ 229