| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Chicago Boston | Outbound 04/03/26 direct UA1693 02h 33min | Return 04/16/26 direct UA1921 02h 44min |  United Airlines |  | ? | $311 | |
| Best option Chicago Boston | Outbound 04/03/26 direct UA2395 02h 31min | Return 04/16/26 direct UA1921 02h 44min | United Airlines | | ? | $312 | |
| Chicago Boston | Outbound 04/03/26 direct UA1117 02h 27min | Return 04/16/26 direct UA1921 02h 44min | United Airlines |  | ? | $328 | |
| Chicago Boston | Outbound 04/03/26 direct B61012 02h 25min | Return 04/16/26 direct B60811 02h 52min |  JetBlue Airways |  | ? | $342 | |
| Chicago Boston | Outbound 04/03/26 1 Stopover (FLL) NK1986, NK2230 09h 44min | Return 04/16/26 1 Stopover (MSP) SY0252, SY0261 08h 04min |  Spirit Airlines |  | $366 | ||
| Chicago Boston | Outbound 04/03/26 direct B61012 02h 25min | Return 04/16/26 direct B60811 02h 52min | JetBlue Airways | | ? | $377 | |
| Chicago Boston | Outbound 04/03/26 1 Stopover (FLL) NK1986, NK2230 09h 44min | Return 04/16/26 1 Stopover (MSP) SY0252, SY0261 08h 04min | Spirit Airlines |  | $381 | ||
| Chicago Boston | Outbound 04/03/26 1 Stopover (FLL) NK1986, NK2230 09h 44min | Return 04/16/26 1 Stopover (MSP) SY0252, SY0261 08h 04min | Spirit Airlines | | $383 | ||
| Chicago Boston | Outbound 04/03/26 1 Stopover (ATL) F91442, F93086 12h 25min | Return 04/16/26 1 Stopover (MSP) SY0252, SY0261 08h 04min |  Frontier Airlines |  | ? | $436 | |
| Chicago Boston | Outbound 04/03/26 direct AA4650 02h 31min | Return 04/16/26 1 Stopover (CVG) AA4760, AA3554 05h 10min |  American Airlines |  | ? | $486 |
Stops
- Direct flight
Airline
- United Airlines
- Spirit Airlines
- American 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
| Roundtrip from | $311.00 |
|---|---|
| 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 $100
- Flight Chicago - Las Vegas from $283
- Flight Chicago - Los Angeles from $358
- Flight Chicago - Miami from $51
- Flight Chicago - San Francisco from $333
- Flight Chicago - Tampa from $298
- Flight Chicago - Denver from $290
- Flight Chicago - Orlando from $264
- Flight Chicago - New Orleans from $232
- Flight Chicago - Atlanta from $243
Alternative flights to Boston
- Flight New York - Boston from $225
- Flight New York - Boston from $340
- Flight Washington-DC - Boston from $117
- Flight Orlando - Boston from $287
- Flight Buffalo - Boston from $387
- Flight Las Vegas - Boston from $352
- Flight Austin - Boston from $183
- Flight Washington DC - Boston from $247
- Flight Fort Lauderdale - Boston from $154
- Flight Atlanta - Boston from $74
Flight destinations with a similar price
- Flight Boston - Amsterdam from $531
- Flight Boston - Aruba from $464
- Flight Boston - Bermuda from $600
- Flight Boston - Cancun from $323
- Flight Boston - Dublin from $321
- Flight Boston - Rome-Fiumicino from $470
- Flight Boston - Frankfurt from $493
- Flight Boston - London Heathrow from $500
- Flight Boston - Mexico City from $570
Flight destinations with a similar price
- Flight Chicago - Las Vegas from $283
- Flight Chicago - San Francisco from $333
- Flight Chicago - Tampa from $298
- Flight Chicago - Denver from $290
- Flight Chicago - Seattle-Tacoma from $333
- Flight Chicago - Phoenix - Sky Harbor from $283
- Flight Chicago - Mexico City from $308
- Flight Chicago - Santa Ana, CA from $310
- Flight Chicago - Guadalajara from $294