| 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 07/25/25 1 Stopover (AVL) G41846, G40269 22h 15min | Return 08/17/25 1 Stopover (TYS) G41426, G43027 26h 30min |  Allegiant Air |  | $271 | ||
| 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 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 10/18/25 1 Stopover (FLL) NK0867, NK0616 08h 10min | Return 10/24/25 direct B60311 02h 54min | Spirit Airlines | | ? | $135 | |
| Chicago Boston | Outbound 10/18/25 direct AA4537 02h 38min | Return 11/17/25 direct AA3477 03h 02min |  American Airlines | | ? | $152 | |
| Chicago Boston | Outbound 07/02/25 direct B61012 02h 36min | Return 07/25/25 direct UA2229 02h 52min | JetBlue Airways |  | ? | $155 |
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 $154
- Flight Chicago - Atlanta from $82
Alternative flights to Boston
- Flight New York - Boston from $95
- Flight Miami - Boston from $140
- Flight New York - Boston from $181
- Flight Tampa - Boston from $146
- Flight Washington-DC - Boston from $127
- Flight Orlando - Boston from $146
- Flight Los Angeles - Boston from $174
- 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 - 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