Flights from Chicago to Boston with Alaska Airlines

Our cheapest offers for flights from Chicago to Boston

Here you can compare cheap flights from Chicago (CHI) to Boston (BOS) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Boston. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
Boston
Outbound
09/25/25
1 Stopover (SEA)
AS0942, AS0460
17h 07min
Return
10/05/25
1 Stopover (SEA)
AS0459, AS0384
24h 04min
Alaska Airlines ?
$729
Prices based on recent searches, subject to last-minute changes
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Important flight information

Flight information: Chicago - Boston

Roundtrip from 212,45 USD
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
Alternative flights to Boston
Flight destinations with a similar price
Flight destinations with a similar price