| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Chicago Boston | Outbound 09/23/25 direct B60312 02h 34min | Return 09/30/25 direct AA4470 03h 04min |  JetBlue Airways |  | ? | $93 | |
| Chicago Boston | Outbound 06/18/25 1 Stopover (ATL) NK1195, NK1180 15h 12min | Return 07/15/25 2 Stopovers (DTW, DFW) NK2328, NK1020, NK0828 28h 55min |  Spirit Airlines |  | $254 | ||
| Chicago Boston | Outbound 09/23/25 direct B61012 02h 30min | Return 09/30/25 direct B60811 02h 50min | JetBlue Airways |  | ? | $99 | |
| Chicago Boston | Outbound 09/23/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | Return 09/30/25 1 Stopover (FLL) NK2887, NK0003 09h 44min | Spirit Airlines |  | $109 | ||
| Chicago Boston | Outbound 09/23/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | Return 09/30/25 1 Stopover (FLL) NK0296, NK1026 12h 27min | Spirit Airlines | | $113 | ||
| Chicago Boston | Outbound 06/18/25 1 Stopover (JFK) B60906, B60618 04h 53min | Return 07/15/25 direct B60811 02h 56min | JetBlue Airways | | ? | $120 | |
| Chicago Boston | Outbound 09/04/25 direct B60312 02h 34min | Return 09/28/25 direct AA3324 02h 58min | JetBlue Airways | | ? | $121 | |
| Chicago Boston | Outbound 09/23/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | Return 09/30/25 1 Stopover (FLL) NK0296, NK1026 12h 27min | Spirit Airlines |  | $122 | ||
| Chicago Boston | Outbound 06/18/25 1 Stopover (JFK) B60906, B60618 04h 53min | Return 07/15/25 direct AA0598 02h 52min | JetBlue Airways | | ? | $128 | |
| Chicago Boston | Outbound 10/18/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | Return 10/24/25 direct B60311 02h 54min | Spirit Airlines | | ? | $135 |
Stops
- Direct flight
Airline
- Spirit Airlines
- JetBlue Airways
- American Airlines
- United Airlines
- 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 | $ 92,34 |
|---|---|
| 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 (ORD, MDW, RFD) (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 $ 86
- Flight Chicago - Las Vegas from $ 128
- Flight Chicago - Los Angeles from $ 103
- Flight Chicago - Miami from $ 98
- Flight Chicago - San Francisco from $ 200
- Flight Chicago - Tampa from $ 117
- Flight Chicago - Denver from $ 146
- Flight Chicago - Orlando from $ 86
- Flight Chicago - New Orleans from $ 139
- Flight Chicago - Atlanta from $ 67
Alternative flights to Boston
- Flight New York - Boston from $ 95
- Flight Miami - Boston from $ 140
- Flight New York - Boston from $ 164
- Flight Tampa - Boston from $ 146
- Flight Washington-DC - Boston from $ 116
- Flight Orlando - Boston from $ 136
- Flight Los Angeles - Boston from $ 172
- Flight Buffalo - Boston from $ 140
- Flight San Francisco - Boston from $ 213
- Flight Las Vegas - Boston from $ 194
Flight destinations with a similar price
- Flight Boston - Amsterdam from $ 320
- Flight Boston - Aruba from $ 353
- Flight Boston - Bermuda from $ 297
- Flight Boston - Paris - Charles de Gaulle from $ 340
- Flight Boston - Cancun from $ 248
- Flight Boston - Dublin from $ 300
- Flight Boston - Rome-Fiumicino from $ 400
- Flight Boston - Frankfurt from $ 445
- Flight Boston - London Heathrow from $ 437
- Flight Boston - Mexico City from $ 368
Flight destinations with a similar price
- Flight Chicago - New York from $ 86
- Flight Chicago - Miami from $ 98
- Flight Chicago - Orlando from $ 86
- Flight Chicago - Dallas from $ 100