| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Chicago Boston | Outbound 02/13/26 direct AA1033 02h 24min | Return 02/26/26 direct B60811 02h 52min |  American Airlines |  | ? | $143 | |
| 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 02/13/26 direct B61012 02h 25min | Return 02/26/26 direct B60811 02h 52min |  JetBlue Airways |  | ? | $217 | |
| 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 02/13/26 direct AA1033 02h 24min | Return 02/26/26 direct AA3477 03h 01min | American Airlines |  | ? | $283 | |
| Chicago Boston | Outbound 02/13/26 1 Stopover (FLL) NK0002, NK3061 12h 06min | Return 02/26/26 1 Stopover (FLL) NK1097, NK1986 12h 35min | Spirit Airlines | | $361 | ||
| Chicago Boston | Outbound 02/13/26 1 Stopover (FLL) NK0002, NK3061 12h 06min | Return 02/26/26 1 Stopover (FLL) NK1097, NK1986 12h 35min | Spirit Airlines |  | $379 |
Stops
- Direct flight
Airline
- Spirit Airlines
- United Airlines
- American 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 | $142.61 |
|---|---|
| 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 $67
- Flight Chicago - Las Vegas from $110
- Flight Chicago - Los Angeles from $172
- Flight Chicago - Miami from $98
- Flight Chicago - San Francisco from $208
- Flight Chicago - Tampa from $69
- Flight Chicago - Denver from $101
- Flight Chicago - Orlando from $130
- Flight Chicago - New Orleans from $103
- Flight Chicago - Atlanta from $181
Alternative flights to Boston
- Flight New York - Boston from $127
- Flight New York - Boston from $127
- Flight Tampa - Boston from $117
- Flight Washington-DC - Boston from $141
- Flight Orlando - Boston from $287
- Flight Buffalo - Boston from $110
- Flight Las Vegas - Boston from $146
- Flight Austin - Boston from $214
- Flight Washington DC - Boston from $203
- Flight Fort Lauderdale - Boston from $119
Flight destinations with a similar price
- Flight Boston - Amsterdam from $433
- Flight Boston - Aruba from $354
- Flight Boston - Bermuda from $393
- Flight Boston - Cancun from $332
- Flight Boston - Dublin from $330
- Flight Boston - Rome-Fiumicino from $385
- Flight Boston - Frankfurt from $373
- Flight Boston - London Heathrow from $436
- Flight Boston - Mexico City from $480
Flight destinations with a similar price
- Flight Chicago - Orlando from $130
- Flight Chicago - Philadelphia from $145
- Flight Chicago - Owensboro from $138