Alaska Airlines Chicago to Boston Flights

Return flight: Boston – Chicago
Page navigation
Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Alaska Airlines flights from Chicago to Boston. Compare airline ticket prices and book air tickets starting from $309 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Alaska Airlines, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — Boston (MA) by Alaska Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in march: one-way - $309, two-way – $530.
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights

Cheap Flights from Chicago to Boston by Alaska Airlines

Look at the list of plane tickets for the most connecting flights by Alaska Airlines, their prices start from $309. There’re no direct flights. The fastest connecting flight – 12h 50m.
Price Departure Arrival Flight Time Airline Flight
from $309
Find flight
10:00 am
Chicago
O'Hare International
 11:59 pm
Boston
Logan
 12h 59m
layover
3h 2m - Seattle
 Alaska Airlines
AS462
AS460
from $316
Find flight
5:54 pm
Chicago
O'Hare International
 7:44 am+1 день
Boston
Logan
 12h 50m
layover
2h 55m - Seattle
 Alaska Airlines
AS353
AS536
Show All Flights
*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 02/22/2025
Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
10:00 am — 11:59 pm
10:00 am — 12:43 pm AS462 Alaska Airlines
Chicago — Seattle
3h 2m stop
3:45 pm — 11:59 pm AS460 Alaska Airlines
Seattle — Boston
12h 59m
including layover
Find flight
from$309
5:54 pm — 7:44 am
+1 day
5:54 pm — 8:35 pm AS353 Alaska Airlines
Chicago — Seattle
2h 55m stop
11:30 pm — 7:44 am AS536 Alaska Airlines
Seattle — Boston
12h 50m
including layover
Find flight
from$316
*Departure and arrival times are local. Last updated on 02/22/2025

Flight Information

There are 3 flights by Alaska Airlines from Chicago to Boston every week with departures from Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee. All flights arrive at Logan, Boston City Heliport, Boston RT128 Rail, Boston South Rail.

Departures start from 10:00 am to 5:54 pm. Nonstop flight is 12h 50m. The time difference between Chicago and Boston is 1h.

  • The fastest flight 12h 50m
  • Average flight time 12h 55m
  • The earliest flight 10:00 am
  • The latest flight 5:54 pm
  • Distance 852 ml

The cheapest months for traveling to Boston are february (from 309 $).

The cheapest flight by Alaska Airlines that our users were able to find is $309. This airfare is economy class on one-way AS462 flight for February 21, 2025 leaving O'Hare International in Chicago at 10:00 am, it includes all taxes and additional fees.

Find same flight?

Alaska Airlines Airplanes on the Route

List of the most popular Alaska Airlines airplanes flying from Chicago to Boston:

Other Popular Airlines on the Route

Besides Alaska Airlines there are other 3 airline carriers between Chicago and Boston. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to Boston.

Nonstop flights

There are 4 direct flights every day from Chicago. Airlines and fares are below:

See more direct flights

Connecting Flights

List of flights with layovers (1 and more stops):

See more connecting flights

How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

Back