$186 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 8/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
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 - Mon, Sep 7
Alaska Airlines Logo
10:28 pm - 7:40 am
ANC
-
ORD
6h 12mnonstop
Alaska Airlines Logo
7:20 am - 11:12 am
ORD
-
ANC
6h 52mnonstop
$373Alaska Airlines
Wed, Aug 26 - Mon, Aug 31
United Airlines Logo
8:00 pm - 5:12 am
ANC
-
ORD
6h 12mnonstop
United Airlines Logo
6:00 am - 2:13 pm
ORD
-
ANC
11h 13m
1 stop
$383United Airlines
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
9:56 pm - 7:25 am
ANC
-
ORD
6h 29mnonstop
American Airlines Logo
4:57 pm - 8:51 pm
ORD
-
ANC
6h 54mnonstop
$386American Airlines
Thu, Sep 24 - Sat, Sep 26
Delta Logo
6:00 am - 4:59 pm
ANC
-
ORD
7h 59m
1 stop
Delta Logo
6:24 pm - 12:45 am
ORD
-
ANC
9h 21m
1 stop
$393Delta
Wed, Sep 2 - Thu, Sep 10
Delta Logo
6:00 am - 6:01 pm
ANC
-
MDW
9h 01m
1 stop
Delta Logo
9:59 am - 5:14 pm
MDW
-
ANC
10h 15m
1 stop
$393Delta
Wed, Sep 2 - Fri, Sep 11
Alaska Airlines Logo
10:28 pm - 7:40 am
ANC
-
ORD
6h 12mnonstop
Alaska Airlines Logo
7:00 pm - 11:15 am
ORD
-
ANC
19h 15m
1 stop
$396Alaska Airlines
Wed, Aug 26 - Mon, Aug 31
Delta Logo
10:30 pm - 4:17 pm
ANC
-
ORD
14h 47m
1 stop
Delta Logo
6:00 am - 4:26 pm
ORD
-
ANC
13h 26m
2 stops
$398Delta
Fri, Sep 25 - Mon, Sep 28
Delta Logo
2:28 pm - 8:48 am
ANC
-
MDW
15h 20m
2 stops
Delta Logo
7:13 pm - 12:45 am
MDW
-
ANC
8h 32m
1 stop
$398Delta
Mon, Aug 17 - Thu, Aug 27
American Airlines Logo
8:00 am - 6:05 am
FAI
-
ORD
19h 05m
1 stop
American Airlines Logo
12:00 pm - 10:54 pm
ORD
-
FAI
13h 54m
1 stop
$444American Airlines
Thu, Oct 22 - Mon, Oct 26
Multiple Airlines Logo
11:15 am - 7:25 am
SIT
-
ORD
17h 10m
2 stops
Multiple Airlines Logo
12:30 pm - 10:58 pm
ORD
-
SIT
13h 28m
2 stops
$642Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$186
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly with an average 28% 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
Schererville
Munster
Chesterton
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 $1,825
Business Class flights to Chicagofrom $809
Premium Economy Class flights to Chicagofrom $1,532
Economy Class flights to Chicagofrom $453