$184 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 8/25. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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

Wed, Aug 26 - Mon, Aug 31
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
$393American Airlines
Thu, Sep 3 - Mon, Sep 7
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
$393American Airlines
Thu, Aug 27 - Thu, Sep 3
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
$405Alaska Airlines
Fri, Aug 21 - Mon, Aug 24
United Airlines Logo
10:19 pm - 2:50 pm
ANC
-
ORD
13h 31m
1 stop
United Airlines Logo
4:05 pm - 7:59 pm
ORD
-
ANC
6h 54mnonstop
$411United Airlines
Fri, Sep 4 - Sat, Sep 12
United Airlines Logo
8:00 pm - 5:12 am
ANC
-
ORD
6h 12mnonstop
United Airlines Logo
8:50 am - 7:02 pm
ORD
-
ANC
13h 12m
1 stop
$411United Airlines
Thu, Sep 3 - Sat, Sep 12
Delta Logo
12:39 am - 11:59 am
ANC
-
ORD
8h 20m
1 stop
Delta Logo
5:44 pm - 12:27 am
ORD
-
ANC
9h 43m
1 stop
$413Delta
Wed, Aug 26 - Mon, Aug 31
Delta Logo
10:30 pm - 4:17 pm
ANC
-
ORD
14h 47m
1 stop
Delta Logo
6:44 pm - 12:59 am
ORD
-
ANC
9h 15m
1 stop
$413Delta
Wed, Aug 26 - Thu, Sep 3
Alaska Airlines Logo
12:29 am - 12:07 pm
ANC
-
ORD
8h 38m
1 stop
Alaska Airlines Logo
7:20 am - 11:12 am
ORD
-
ANC
6h 52mnonstop
$415Alaska Airlines
Fri, Sep 4 - Mon, Sep 7
Multiple Airlines Logo
10:28 pm - 7:40 am
ANC
-
ORD
6h 12mnonstop
Multiple Airlines Logo
5:30 pm - 11:39 pm
ORD
-
ANC
33h 09m
3 stops
$736Multiple Airlines
Fri, Aug 21 - Tue, Aug 25
Multiple Airlines Logo
5:59 pm - 7:25 am
OME
-
ORD
10h 26m
1 stop
Multiple Airlines Logo
4:57 pm - 5:09 pm
ORD
-
OME
27h 12m
1 stop
$1,159Multiple Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$184
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
Schererville
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 $1,806
Business Class flights to Chicagofrom $809
Premium Economy Class flights to Chicagofrom $1,314
Economy Class flights to Chicagofrom $383