Alaska Airlines Boston to Chicago Flights

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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 $434 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 may: one-way - $434, two-way – $744.

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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 $434. There’re no direct flights. The fastest connecting flight – 12h 8m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $708 Find flight	7:10 am Boston Logan	6:18 pm Chicago O'Hare International	12h 8m layover 1h 5m - San Francisco	Alaska Airlines	AS547 AS332
from $714 Find flight	7:10 am Boston Logan	5:00 am+1 день Chicago O'Hare International	22h 50m layover 11h 50m - San Francisco	Alaska Airlines	AS547 AS470
from $993 Find flight	4:45 pm Boston Logan	5:03 am+1 день Chicago O'Hare International	13h 18m layover 3h 10m - Seattle	Alaska Airlines	AS304 AS328
from $434 Find flight	4:45 pm Boston Logan	6:56 am+1 день Chicago O'Hare International	15h 11m layover 1h 50m - Seattle 2h 23m - Portland	Alaska Airlines	AS304 AS1012 AS2014
from $434 Find flight	4:45 pm Boston Logan	6:56 am+1 день Chicago O'Hare International	15h 11m layover 2h 20m - Seattle 1h 54m - Portland	Alaska Airlines	AS304 AS1460 AS2014

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 04/25/2024

Alaska Airlines Flight Schedule Boston to Chicago

Below is a detailed 2024 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	Flight Details	Flight Time	Price
4:45 pm — 6:56 am +1 day	4:45 pm — 7:55 pm AS304 Alaska Airlines Boston — Seattle 1h 50m stop 9:45 pm — 10:38 pm AS1012 Alaska Airlines Seattle — Portland 2h 23m stop 1:01 am — 6:56 am AS2014 Alaska Airlines Portland — Chicago	15h 11m including layover	Find flight from$434
4:45 pm — 6:56 am +1 day	4:45 pm — 7:55 pm AS304 Alaska Airlines Boston — Seattle 2h 20m stop 10:15 pm — 11:07 pm AS1460 Alaska Airlines Seattle — Portland 1h 54m stop 1:01 am — 6:56 am AS2014 Alaska Airlines Portland — Chicago	15h 11m including layover	Find flight from$434
4:45 pm — 5:03 am +1 day	4:45 pm — 7:55 pm AS304 Alaska Airlines Boston — Seattle 3h 10m stop 11:05 pm — 5:03 am AS328 Alaska Airlines Seattle — Chicago	13h 18m including layover	Find flight from$993
7:10 am — 6:18 pm	7:10 am — 10:50 am AS547 Alaska Airlines Boston — San Francisco 1h 5m stop 11:55 am — 6:18 pm AS332 Alaska Airlines San Francisco — Chicago	12h 8m including layover	Find flight from$708
7:10 am — 5:00 am +1 day	7:10 am — 10:50 am AS547 Alaska Airlines Boston — San Francisco 11h 50m stop 10:40 pm — 5:00 am AS470 Alaska Airlines San Francisco — Chicago	22h 50m including layover	Find flight from$714

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 04/25/2024

Flight Information

There are 6 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 4:45 pm to 7:10 am. Nonstop flight is 12h 8m. The time difference between Boston and Chicago is 1h.

The fastest flight 12h 8m
Average flight time 15h 11m
The earliest flight 4:45 pm
The latest flight 7:10 am
Distance 852 ml

The cheapest months for traveling to Chicago are may (from 434 $).

The cheapest flight by Alaska Airlines that our users were able to find is $434. This airfare is economy class on one-way AS304 flight for May 31, 2023 leaving Logan in Boston at 4:45 pm, 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 1 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 2 direct flights every day from Boston. Airlines and fares are below:

B6 - JetBlue

from $76

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Connecting Flights

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

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How to book an air ticket yourself?

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