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 $202 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 january: one-way - $202, two-way – $346.

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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 $202. There’re no direct flights. The fastest connecting flight – 12h 18m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $202 Find flight	7:00 am Boston Logan	6:18 pm Chicago O'Hare International	12h 18m layover 1h 34m - Seattle	Alaska Airlines	AS459 AS410
from $272 Find flight	7:19 pm Boston Logan	11:59 pm+1 день Chicago O'Hare International	29h 40m layover 19h 27m - Seattle	Alaska Airlines	AS537 AS538
from $380 Find flight	6:30 pm Boston Logan	4:48 pm+1 день Chicago O'Hare International	23h 18m layover 12h 19m - San Francisco	Alaska Airlines	AS357 AS598
from $380 Find flight	7:59 pm Boston Logan	1:02 pm+1 день Chicago O'Hare International	18h 3m layover 7h 47m - Portland	Alaska Airlines	AS311 AS324
from $399 Find flight	5:25 pm Boston Logan	11:59 pm+1 день Chicago O'Hare International	31h 34m layover 21h 22m - Seattle	Alaska Airlines	AS364 AS538
from $399 Find flight	5:25 pm Boston Logan	12:09 pm+1 день Chicago O'Hare International	19h 44m layover 9h 16m - Seattle	Alaska Airlines	AS364 AS408
from $600 Find flight	5:25 pm Boston Logan	4:58 pm+1 день Chicago O'Hare International	24h 33m layover 14h 6m - Seattle	Alaska Airlines	AS364 AS352

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 01/21/2025

Alaska Airlines Flight Schedule Boston to Chicago

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	Flight Details	Flight Time	Price
5:25 pm — 11:59 pm +1 day	5:25 pm — 8:44 pm AS364 Alaska Airlines Boston — Seattle 21h 22m stop 6:06 pm — 11:59 pm AS538 Alaska Airlines Seattle — Chicago	31h 34m including layover	Find flight from$399
5:25 pm — 12:09 pm +1 day	5:25 pm — 8:44 pm AS364 Alaska Airlines Boston — Seattle 9h 16m stop 6:00 am — 12:09 pm AS408 Alaska Airlines Seattle — Chicago	19h 44m including layover	Find flight from$399
5:25 pm — 4:58 pm +1 day	5:25 pm — 8:44 pm AS364 Alaska Airlines Boston — Seattle 14h 6m stop 10:50 am — 4:58 pm AS352 Alaska Airlines Seattle — Chicago	24h 33m including layover	Find flight from$600
6:30 pm — 4:48 pm +1 day	6:30 pm — 10:08 pm AS357 Alaska Airlines Boston — San Francisco 12h 19m stop 10:27 am — 4:48 pm AS598 Alaska Airlines San Francisco — Chicago	23h 18m including layover	Find flight from$380
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$202
7:00 am — 12:09 pm +1 day	7:00 am — 10:21 am AS459 Alaska Airlines Boston — Seattle 19h 39m stop 6:00 am — 12:09 pm AS408 Alaska Airlines Seattle — Chicago	30h 9m including layover	Find flight from$351
7:00 am — 11:59 pm	7:00 am — 10:21 am AS459 Alaska Airlines Boston — Seattle 7h 45m stop 6:06 pm — 11:59 pm AS538 Alaska Airlines Seattle — Chicago	17h 59m including layover	Find flight from$370
7:19 pm — 11:59 pm +1 day	7:19 pm — 10:39 pm AS537 Alaska Airlines Boston — Seattle 19h 27m stop 6:06 pm — 11:59 pm AS538 Alaska Airlines Seattle — Chicago	29h 40m including layover	Find flight from$272
7:19 pm — 12:09 pm +1 day	7:19 pm — 10:39 pm AS537 Alaska Airlines Boston — Seattle 7h 21m stop 6:00 am — 12:09 pm AS408 Alaska Airlines Seattle — Chicago	17h 50m including layover	Find flight from$272
7:19 pm — 4:58 pm +1 day	7:19 pm — 10:39 pm AS537 Alaska Airlines Boston — Seattle 12h 11m stop 10:50 am — 4:58 pm AS352 Alaska Airlines Seattle — Chicago	22h 39m including layover	Find flight from$473
7:59 pm — 1:02 pm +1 day	7:59 pm — 11:13 pm AS311 Alaska Airlines Boston — Portland 7h 47m stop 7:00 am — 1:02 pm AS324 Alaska Airlines Portland — Chicago	18h 3m including layover	Find flight from$380

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

*Departure and arrival times are local. Last updated on 01/21/2025

Flight Information

There are 12 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 5:25 pm to 7:59 pm. Nonstop flight is 12h 18m. The time difference between Boston and Chicago is 1h.

The fastest flight 12h 18m
Average flight time 22h 39m
The earliest flight 5:25 pm
The latest flight 7:59 pm
Distance 852 ml

The cheapest months for traveling to Chicago are december (from 202 $), november (from 272 $).

The cheapest flight by Alaska Airlines that our users were able to find is $202. 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 6 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 6 direct flights every day from Boston. Airlines and fares are below:

UA - United Airlines

from $115

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Connecting Flights

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

PD - Porter Airlines

from $297

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UA - United Airlines

from $124

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NK - Spirit Airlines

from $59

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F9 - Frontier Airlines

from $63

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LX - SWISS International Air Lines

from $5648

Find
TS - Air Transat

from $318

Find

See more connecting flights

How to book an air ticket yourself?

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