| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Chicago Boston | Outbound 11/09/25 direct UA0618 02h 24min | Return 12/07/25 direct UA2040 03h 00min |  United Airlines |  | ? | $195 | |
| Chicago Boston | Outbound 11/09/25 direct UA0618 02h 24min | Return 12/07/25 direct UA1015 03h 00min | United Airlines |  | $204 | ||
| Chicago Boston | Outbound 09/25/25 1 Stopover (FLL) NK1380, NK0449 11h 00min | Return 10/05/25 1 Stopover (BNA) NK2301, NK1765 28h 07min |  Spirit Airlines |  | $213 | ||
| Chicago Boston | Outbound 11/09/25 direct UA0618 02h 24min | Return 12/07/25 direct UA1015 03h 00min | United Airlines |  | ? | $224 | |
| Chicago Boston | Outbound 11/09/25 1 Stopover (JFK) B62106, B60618 08h 53min | Return 12/07/25 direct B60311 02h 58min |  JetBlue Airways |  | ? | $234 | |
| Chicago Boston | Outbound 11/09/25 2 Stopovers (BNA, CLT) NK0416, NK2480, NK0507 26h 30min | Return 12/07/25 1 Stopover (FLL) NK2068, NK0001 13h 23min | Spirit Airlines |  | $243 | ||
| Chicago Boston | Outbound 09/25/25 1 Stopover (FLL) NK1380, NK0449 11h 00min | Return 10/05/25 direct B60311 02h 57min | Spirit Airlines | | ? | $246 | |
| Chicago Boston | Outbound 09/25/25 direct AA3710 02h 27min | Return 10/05/25 1 Stopover (PHL) AA1540, AA2095 05h 38min |  American Airlines | | ? | $316 | |
| Chicago Boston | Outbound 09/25/25 direct B60312 02h 29min | Return 10/05/25 direct B60311 02h 57min | JetBlue Airways | | ? | $349 | |
| Chicago Boston | Outbound 09/25/25 1 Stopover (PHL) AA2098, AA1257 04h 26min | Return 10/05/25 direct AA3324 02h 51min | American Airlines | | ? | $357 |
Stops
- Direct flight
Airline
- American Airlines
- United Airlines
- Spirit Airlines
- JetBlue Airways
- Alaska 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 | $ 194,20 |
|---|---|
| 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 $ 106
- Flight Chicago - Las Vegas from $ 110
- Flight Chicago - Los Angeles from $ 91
- Flight Chicago - Miami from $ 98
- Flight Chicago - San Francisco from $ 156
- Flight Chicago - Tampa from $ 56
- Flight Chicago - Denver from $ 101
- Flight Chicago - Orlando from $ 130
- Flight Chicago - New Orleans from $ 103
- Flight Chicago - Atlanta from $ 57
Alternative flights to Boston
- Flight New York - Boston from $ 127
- Flight New York - Boston from $ 127
- Flight Washington-DC - Boston from $ 141
- Flight Orlando - Boston from $ 56
- Flight Buffalo - Boston from $ 110
- Flight Austin - Boston from $ 215
- Flight Washington DC - Boston from $ 203
- Flight Fort Lauderdale - Boston from $ 119
- Flight Atlanta - Boston from $ 90
- Flight Chicago O'Hare - Boston from $ 195
Flight destinations with a similar price
- Flight Boston - Vienna from $ 489
- Flight Boston - London from $ 436
- Flight Boston - Sydney from $ 973
- Flight Boston - Aruba from $ 354
- Flight Boston - Bermuda from $ 379
- Flight Boston - Vancouver from $ 322
- Flight Boston - Toronto from $ 196
- Flight Boston - Toronto - City Centre from $ 202
- Flight Boston - Zurich from $ 448
- Flight Boston - Shanghai Pudong from $ 932
Flight destinations with a similar price
- Flight Chicago - Portland-Oregon from $ 195
- Flight Chicago - Louisville from $ 192
- Flight Chicago - Santa Ana, CA from $ 191
- Flight Chicago - Jacksonville, Florida from $ 204
- Flight Chicago - Appleton from $ 187
- Flight Chicago - Toronto from $ 197