$183 Find Cheap Flights from Alaska to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 6/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Alaska to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Alaska to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Alaska to Chicago

Mon, May 18 - Sun, May 24
Alaska Airlines Logo
11:08 pm - 8:25 am
ANC
-
ORD
6h 17mnonstop
Alaska Airlines Logo
6:00 am - 12:04 pm
ORD
-
ANC
9h 04m
1 stop
$360Alaska Airlines
Mon, May 18 - Sun, May 24
Alaska Airlines Logo
7:40 am - 11:59 pm
ANC
-
ORD
13h 19m
1 stop
Alaska Airlines Logo
6:00 am - 12:04 pm
ORD
-
ANC
9h 04m
1 stop
$363Alaska Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
9:50 pm - 7:23 am
ANC
-
ORD
6h 33mnonstop
American Airlines Logo
5:02 pm - 8:41 pm
ORD
-
ANC
6h 39mnonstop
$367American Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
7:00 am - 8:11 pm
ANC
-
ORD
10h 11m
1 stop
American Airlines Logo
5:02 pm - 8:41 pm
ORD
-
ANC
6h 39mnonstop
$377American Airlines
Wed, May 27 - Wed, Jun 10
Alaska Airlines Logo
11:08 pm - 8:25 am
ANC
-
ORD
6h 17mnonstop
Alaska Airlines Logo
8:05 pm - 8:40 am
ORD
-
ANC
15h 35m
1 stop
$383Alaska Airlines
Wed, May 27 - Mon, Jun 8
Delta Logo
9:30 pm - 1:01 pm
ANC
-
ORD
12h 31m
1 stop
Delta Logo
7:01 am - 9:16 pm
ORD
-
ANC
17h 15m
1 stop
$387Delta
Mon, May 18 - Sun, May 24
Delta Logo
6:00 am - 5:56 pm
ANC
-
MDW
8h 56m
1 stop
Delta Logo
6:23 am - 6:38 pm
MDW
-
ANC
15h 15m
1 stop
$387Delta
Wed, Aug 26 - Sun, Aug 30
United Airlines Logo
11:59 pm - 9:09 am
ANC
-
ORD
6h 10mnonstop
United Airlines Logo
6:00 am - 2:05 pm
ORD
-
ANC
11h 05m
1 stop
$389United Airlines
Fri, May 29 - Tue, Jun 9
Delta Logo
1:55 am - 5:13 pm
ANC
-
ORD
12h 18m
1 stop
Delta Logo
7:45 am - 8:07 pm
ORD
-
ANC
15h 22m
2 stops
$392Delta
Sun, May 24 - Sun, May 31
Delta Logo
6:00 am - 9:09 pm
ANC
-
MDW
12h 09m
2 stops
Delta Logo
9:22 am - 8:16 pm
MDW
-
ANC
13h 54m
1 stop
$392Delta
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Good to know

Low seasonJanuary
Cheapest flight$183
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Anchorage to Chicago O'Hare Airport

FAQs for booking flights from Alaska to Chicago

  • How does KAYAK find such low prices on flights from Alaska to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Alaska to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Alaska to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Alaska is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Alaska to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Alaska with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Alaska to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Alaska up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Alaska

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.