$211 Find Cheap Flights from Alaska to Chicago - Compare and Save

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 10/1. 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

Thu, Sep 3 - Wed, Sep 9
Alaska Airlines Logo
10:28 pm - 7:40 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 12mnonstop
Alaska Airlines Logo
8:00 am - 6:38 pmORD  Chicago O'Hare Intl-ANC Anchorage
13h 38m1 stop Seattle/Tacoma Intl
$411Alaska Airlines
Thu, Sep 3 - Wed, Sep 9
Alaska Airlines Logo
10:28 pm - 7:40 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 12mnonstop
Alaska Airlines Logo
6:00 am - 12:59 pmORD  Chicago O'Hare Intl-ANC Anchorage
9h 59m1 stop Seattle/Tacoma Intl
$420Alaska Airlines
Tue, Sep 22 - Thu, Oct 1
American Airlines Logo
9:54 pm - 7:25 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 31mnonstop
American Airlines Logo
4:53 pm - 8:49 pmORD  Chicago O'Hare Intl-ANC Anchorage
6h 56mnonstop
$423American Airlines
Thu, Oct 1 - Mon, Oct 5
United Airlines Logo
8:59 pm - 6:10 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 11mnonstop
United Airlines Logo
4:05 pm - 7:57 pmORD  Chicago O'Hare Intl-ANC Anchorage
6h 52mnonstop
$423United Airlines
Thu, Oct 1 - Tue, Oct 6
United Airlines Logo
8:59 pm - 6:10 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 11mnonstop
United Airlines Logo
4:05 pm - 7:57 pmORD  Chicago O'Hare Intl-ANC Anchorage
6h 52mnonstop
$423United Airlines
Thu, Sep 17 - Wed, Sep 23
American Airlines Logo
9:54 pm - 7:25 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 31mnonstop
American Airlines Logo
4:53 pm - 8:49 pmORD  Chicago O'Hare Intl-ANC Anchorage
6h 56mnonstop
$424American Airlines
Thu, Sep 3 - Wed, Sep 9
Delta Logo
6:00 am - 6:01 pmANC  Anchorage-MDW Chicago Midway
9h 01m1 stop Minneapolis St Paul
Delta Logo
2:00 pm - 9:00 pmMDW  Chicago Midway-ANC Anchorage
10h 00m1 stop Minneapolis St Paul
$443Delta
Tue, Oct 13 - Tue, Oct 27
Delta Logo
11:29 am - 11:34 pmANC  Anchorage-ORD Chicago O'Hare Intl
9h 05m1 stop Seattle/Tacoma Intl
Delta Logo
9:59 am - 8:59 pmORD  Chicago O'Hare Intl-ANC Anchorage
14h 00m1 stop Minneapolis St Paul
$443Delta
Thu, Sep 3 - Wed, Sep 9
Southwest Logo
11:55 pm - 5:00 pmANC  Anchorage-MDW Chicago Midway
14h 05m2 stops Las Vegas Harry Reid Intl Wichita Eisenhower National
Southwest Logo
10:30 am - 10:45 pmMDW  Chicago Midway-ANC Anchorage
15h 15m2 stops Des Moines Las Vegas Harry Reid Intl
$453Southwest
Thu, Sep 3 - Wed, Sep 9
Southwest Logo
11:55 pm - 5:00 pmANC  Anchorage-MDW Chicago Midway
14h 05m2 stops Las Vegas Harry Reid Intl Wichita Eisenhower National
Southwest Logo
10:30 am - 10:45 pmMDW  Chicago Midway-ANC Anchorage
15h 15m2 stops Des Moines Las Vegas Harry Reid Intl
$483Southwest
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Good to know

Low season

January

Cheapest flight

$211
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 7% 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
Munster
Chesterton
Schererville
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.
First Class flights to Chicagofrom $1,806
Business Class flights to Chicagofrom $809
Premium Economy Class flights to Chicagofrom $1,314
Economy Class flights to Chicagofrom $281