Alaska Airlines Boston to Chicago Flights

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

Cheapflightsplus.com will find cheap Alaska Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $215 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 Boston (MA) — Chicago (IL) 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 december: one-way - $215, two-way – $369.
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Cheap Flights from Boston to Chicago by Alaska Airlines

Look at the list of plane tickets for the most connecting flights by Alaska Airlines, their prices start from $215. There’re no direct flights. The fastest connecting flight – 12h 18m.
Price Departure Arrival Flight Time Airline Flight
from $215
Find flight
7:00 am
Boston
Logan
 6:18 pm
Chicago
O'Hare International
 12h 18m
layover
1h 34m - Seattle
 Alaska Airlines
AS459
AS410
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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 12/03/2024
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
7:00 am — 6:18 pm
7:00 am — 10:37 am AS459 Alaska Airlines
Boston — Seattle
1h 34m stop
12:11 pm — 6:18 pm AS410 Alaska Airlines
Seattle — Chicago
12h 18m
including layover
Find flight
from$215
*Departure and arrival times are local. Last updated on 12/03/2024

Flight Information

There are 2 flights by Alaska Airlines from Boston to Chicago every week with departures from Logan, Boston City Heliport, Boston RT128 Rail, Boston South Rail. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 7:00 am to 7:00 am. Nonstop flight is 12h 18m. The time difference between Boston and Chicago is 1h.

  • The fastest flight 12h 18m
  • Average flight time 12h 18m
  • The earliest flight 7:00 am
  • The latest flight 7:00 am
  • Distance 852 ml

The cheapest months for traveling to Chicago are december (from 215 $).

The cheapest flight by Alaska Airlines that our users were able to find is $215. This airfare is economy class on one-way AS459 flight for December 10, 2024 leaving Logan in Boston at 7:00 am, it includes all taxes and additional fees.

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Alaska Airlines Airplanes on the Route

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

Other Popular Airlines on the Route

Besides Alaska Airlines there are other 9 airline carriers between Boston and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Boston to Chicago.

Nonstop flights

There are 13 direct flights every day from Boston. Airlines and fares are below:

See more direct flights

Connecting Flights

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

  • PD - Porter Airlines
    from $277
    Find
  • UA - United Airlines
    from $132
    Find
  • NK - Spirit Airlines
    from $56
    Find
  • F9 - Frontier Airlines
    from $59
    Find
  • OS - Austrian Airlines
    from $6303
    Find
  • TK - Turkish Airlines
    from $1910
    Find
  • TP - TAP Portugal
    from $1058
    Find
  • LX - SWISS International Air Lines
    from $5946
    Find
  • TS - Air Transat
    from $329
    Find
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.

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