$195 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 5/19. 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

Sat, Apr 18 - Wed, Apr 22
United Airlines Logo
8:50 pm - 6:05 am
ANC
-
ORD
6h 15mnonstop
United Airlines Logo
4:03 pm - 7:48 pm
ORD
-
ANC
6h 45mnonstop
$397United Airlines
Tue, Apr 21 - Tue, Apr 28
Alaska Airlines Logo
7:05 am - 4:56 pm
ANC
-
ORD
30h 51m
1 stop
Alaska Airlines Logo
8:48 pm - 12:03 pm
ORD
-
ANC
18h 15m
1 stop
$406Alaska Airlines
Tue, Apr 14 - Tue, Apr 21
United Airlines Logo
8:50 pm - 6:05 am
ANC
-
ORD
6h 15mnonstop
United Airlines Logo
2:35 pm - 10:45 pm
ORD
-
ANC
11h 10m
1 stop
$407United Airlines
Sun, Jun 7 - Sun, Jun 14
Alaska Airlines Logo
11:08 pm - 8:25 am
ANC
-
ORD
6h 17mnonstop
Alaska Airlines Logo
12:59 am - 4:44 am
ORD
-
ANC
6h 45mnonstop
$409Alaska Airlines
Thu, May 21 - Tue, May 26
American Airlines Logo
9:53 pm - 7:21 am
ANC
-
ORD
6h 28mnonstop
American Airlines Logo
3:22 pm - 11:52 pm
ORD
-
ANC
11h 30m
1 stop
$413American Airlines
Wed, Apr 22 - Sun, Apr 26
Delta Logo
1:30 am - 1:23 pm
ANC
-
ORD
8h 53m
1 stop
Delta Logo
7:15 am - 12:25 am
ORD
-
ANC
20h 10m
1 stop
$417Delta
Tue, Apr 21 - Fri, Apr 24
Delta Logo
9:15 pm - 8:46 am
ANC
-
MDW
8h 31m
1 stop
Delta Logo
9:29 am - 6:46 pm
MDW
-
ANC
12h 17m
1 stop
$417Delta
Fri, Sep 11 - Sun, Sep 13
Alaska Airlines Logo
6:00 am - 11:59 pm
ANC
-
ORD
14h 59m
1 stop
Alaska Airlines Logo
9:30 am - 1:18 pm
ORD
-
ANC
6h 48mnonstop
$419Alaska Airlines
Sat, Apr 18 - Tue, Apr 21
Alaska Airlines Logo
3:53 pm - 6:39 am
FAI
-
ORD
11h 46m
1 stop
Alaska Airlines Logo
6:00 am - 10:35 pm
ORD
-
FAI
19h 35m
1 stop
$420Alaska Airlines
Sun, Jul 26 - Wed, Jul 29
American Airlines Logo
5:30 am - 8:18 pm
FAI
-
ORD
11h 48m
1 stop
American Airlines Logo
11:40 am - 2:15 am
ORD
-
FAI
17h 35m
1 stop
$480American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$195
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 33% increase in price.
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
Griffith
Saint John

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.