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 | | ![]() | ? | $143 | |
Chicago Boston | Outbound 11/09/25 direct UA0618 02h 24min | Return 12/07/25 direct UA2040 03h 00min | | ![]() | ? | $195 | |
Chicago Boston | Outbound 11/09/25 direct UA0618 02h 24min | Return 12/07/25 direct UA1015 03h 00min | | ![]() | $204 | ||
Chicago Boston | Outbound 02/13/26 direct B61012 02h 25min | Return 02/26/26 direct B60811 02h 52min | | ![]() | ? | $217 | |
Chicago Boston | Outbound 11/09/25 direct UA0618 02h 24min | Return 12/07/25 direct UA1015 03h 00min | | ![]() | ? | $224 | |
Chicago Boston | Outbound 11/09/25 1 Stopover (JFK) B62106, B60618 08h 53min | Return 12/07/25 direct B60311 02h 58min | | ![]() | ? | $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 | | ![]() | $243 | ||
Chicago Boston | Outbound 02/13/26 direct AA1033 02h 24min | Return 02/26/26 direct AA3477 03h 01min | | ![]() | ? | $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 | | ![]() | $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 | | ![]() | $379 |
Stops
- Direct flight
Airline
- Spirit Airlines
- United 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 | $ 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 $ 78
- Flight Chicago - Las Vegas from $ 110
- Flight Chicago - Los Angeles from $ 172
- Flight Chicago - Miami from $ 98
- Flight Chicago - San Francisco from $ 157
- 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 Washington-DC - Boston from $ 141
- Flight Orlando - Boston from $ 56
- Flight Buffalo - Boston from $ 110
- Flight Las Vegas - Boston from $ 146
- Flight Austin - Boston from $ 179
- Flight Washington DC - Boston from $ 203
- Flight Fort Lauderdale - Boston from $ 119
- Flight Atlanta - Boston from $ 90
Flight destinations with a similar price
- Flight Boston - Vienna from $ 489
- Flight Boston - Sydney from $ 994
- Flight Boston - Aruba from $ 354
- Flight Boston - Sarajevo from $ 389
- Flight Boston - Bermuda from $ 379
- Flight Boston - Vancouver from $ 322
- Flight Boston - Toronto from $ 213
- Flight Boston - Toronto from $ 213
- Flight Boston - Toronto - City Centre from $ 217
- Flight Boston - Zurich from $ 448
Flight destinations with a similar price
- Flight Chicago - San Francisco from $ 157
- Flight Chicago - Orlando from $ 130
- Flight Chicago - Philadelphia from $ 136
- Flight Chicago - Owensboro from $ 138