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.

$221 CHEAP FLIGHTS from Alaska to Chicago

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Cheap Flights from Alaska to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Alaska to Chicago

Mon, Sep 28 - Thu, Oct 1

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$443American Airlines

Tue, Sep 29 - Wed, Oct 14

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

9:40 am - 7:17 pmORD Chicago O'Hare Intl-ANC Anchorage

12h 37m1 stop Dallas/Fort Worth

$453American Airlines

Mon, Oct 12 - Mon, Oct 19

11:45 pm - 11:28 amANC Anchorage-ORD Chicago O'Hare Intl

8h 43m1 stop Denver Intl

4:05 pm - 7:57 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 52mnonstop

$453United Airlines

Tue, Sep 29 - Tue, Oct 6

8:59 pm - 6:10 amANC Anchorage-ORD Chicago O'Hare Intl

6h 11mnonstop

2:30 pm - 10:43 pmORD Chicago O'Hare Intl-ANC Anchorage

11h 13m1 stop Denver Intl

$453United Airlines

Fri, Oct 16 - Sun, Oct 18

6:30 am - 11:34 pmANC Anchorage-ORD Chicago O'Hare Intl

14h 04m1 stop Seattle/Tacoma Intl

6:35 am - 1:28 pmORD Chicago O'Hare Intl-ANC Anchorage

9h 53m1 stop Seattle/Tacoma Intl

$463Delta

Fri, Oct 2 - Sat, Oct 3

1:32 am - 1:29 pmANC Anchorage-ORD Chicago O'Hare Intl

8h 57m1 stop Seattle/Tacoma Intl

5:44 pm - 12:27 amORD Chicago O'Hare Intl-ANC Anchorage

9h 43m1 stop Seattle/Tacoma Intl

$463Delta

Sun, Oct 18 - Wed, Oct 21

1:31 am - 6:20 pmANC Anchorage-ORD Chicago O'Hare Intl

13h 49m1 stop Seattle/Tacoma Intl

9:00 am - 11:39 pmORD Chicago O'Hare Intl-ANC Anchorage

17h 39m1 stop Seattle/Tacoma Intl

$463Alaska Airlines

Sun, Sep 27 - Wed, Oct 14

12:29 am - 12:07 pmANC Anchorage-ORD Chicago O'Hare Intl

8h 38m1 stop Seattle/Tacoma Intl

7:00 am - 2:45 pmORD Chicago O'Hare Intl-ANC Anchorage

10h 45m1 stop Seattle/Tacoma Intl

$463Alaska Airlines

Sat, Sep 19 - Mon, Sep 21

6:17 pm - 6:20 amANC Anchorage-ORD Chicago O'Hare Intl

9h 03m1 stop Seattle/Tacoma Intl

5:30 pm - 12:28 pmORD Chicago O'Hare Intl-ANC Anchorage

21h 58m2 stops Calgary Seattle/Tacoma Intl

$987Multiple Airlines

Sat, Sep 19 - Sun, Sep 20

6:17 pm - 6:20 amANC Anchorage-ORD Chicago O'Hare Intl

9h 03m1 stop Seattle/Tacoma Intl

5:30 pm - 11:15 amORD Chicago O'Hare Intl-ANC Anchorage

20h 45m2 stops Calgary Seattle/Tacoma Intl

$987Multiple Airlines

Recent last minute flight deals from Alaska to Chicago

Wed, Sep 2 - Sat, Oct 3

9:56 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 29mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$499American Airlines

Wed, Sep 2 - Sat, Oct 3

10:10 pm - 11:37 amANC Anchorage-ORD Chicago O'Hare Intl

10h 27m1 stop Minneapolis St Paul

12:29 pm - 9:00 pmORD Chicago O'Hare Intl-ANC Anchorage

11h 31m1 stop Minneapolis St Paul

$501Delta

Wed, Sep 2 - Sat, Oct 3

7:00 am - 8:30 pmANC Anchorage-ORD Chicago O'Hare Intl

10h 30m1 stop Dallas/Fort Worth

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$509American Airlines

Thu, Sep 3 - Mon, Sep 7

10:28 pm - 7:40 amANC Anchorage-ORD Chicago O'Hare Intl

6h 12mnonstop

7:20 am - 11:12 amORD Chicago O'Hare Intl-ANC Anchorage

6h 52mnonstop

$519Alaska Airlines

Mon, Aug 31 - Wed, Sep 2

9:20 pm - 6:32 amANC Anchorage-ORD Chicago O'Hare Intl

6h 12mnonstop

4:05 pm - 7:59 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 54mnonstop

$519United Airlines

Mon, Aug 31 - Thu, Sep 3

8:00 pm - 5:12 amANC Anchorage-ORD Chicago O'Hare Intl

6h 12mnonstop

4:05 pm - 7:59 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 54mnonstop

$519United Airlines

Tue, Sep 1 - Sat, Oct 3

2:28 am - 7:21 pmANC Anchorage-ORD Chicago O'Hare Intl

13h 53m2 stops Seattle/Tacoma Intl San Diego

9:00 am - 9:48 pmORD Chicago O'Hare Intl-ANC Anchorage

15h 48m1 stop Seattle/Tacoma Intl

$524Alaska Airlines

Wed, Sep 2 - Fri, Sep 4

10:10 pm - 1:10 pmANC Anchorage-MDW Chicago Midway

12h 00m1 stop Minneapolis St Paul

9:24 am - 9:20 pmMDW Chicago Midway-ANC Anchorage

14h 56m1 stop Detroit Metropolitan Wayne County

$539Delta

Mon, Aug 31 - Wed, Sep 2

11:55 pm - 1:30 pmANC Anchorage-MDW Chicago Midway

10h 35m1 stop Las Vegas Harry Reid Intl

10:30 am - 10:45 pmMDW Chicago Midway-ANC Anchorage

15h 15m2 stops Des Moines Las Vegas Harry Reid Intl

$544Southwest

Mon, Aug 31 - Wed, Sep 2

10:25 pm - 1:55 pmANC Anchorage-MDW Chicago Midway

12h 30m2 stops Denver Intl Lambert-St Louis

10:30 am - 10:45 pmMDW Chicago Midway-ANC Anchorage

15h 15m2 stops Des Moines Las Vegas Harry Reid Intl

$642Southwest

Recent direct flight deals from Alaska to Chicago

Mon, Sep 28 - Thu, Oct 1

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$443American Airlines

Tue, Sep 22 - Tue, Sep 29

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$461American Airlines

Thu, Sep 24 - Thu, Oct 1

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$461American Airlines

Mon, Nov 2 - Tue, Nov 10

8:43 pm - 5:59 amANC Anchorage-ORD Chicago O'Hare Intl

6h 16mnonstop

3:35 pm - 7:39 pmORD Chicago O'Hare Intl-ANC Anchorage

7h 04mnonstop

$463United Airlines

Mon, Oct 12 - Sun, Nov 1

8:59 pm - 6:10 amANC Anchorage-ORD Chicago O'Hare Intl

6h 11mnonstop

3:35 pm - 7:39 pmORD Chicago O'Hare Intl-ANC Anchorage

7h 04mnonstop

$473United Airlines

Fri, Sep 25 - Fri, Oct 2

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$479American Airlines

Sun, Sep 27 - Sun, Oct 4

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$479American Airlines

Wed, Sep 23 - Sat, Sep 26

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$479American Airlines

Sat, Sep 26 - Sat, Oct 3

9:54 pm - 7:25 amANC Anchorage-ORD Chicago O'Hare Intl

6h 31mnonstop

4:53 pm - 8:49 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 56mnonstop

$479American Airlines

Fri, Oct 16 - Sun, Oct 18

8:59 pm - 6:10 amANC Anchorage-ORD Chicago O'Hare Intl

6h 11mnonstop

4:05 pm - 7:57 pmORD Chicago O'Hare Intl-ANC Anchorage

6h 52mnonstop

$479United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$221

Best time to beat the crowds but there is an average 17% increase in price.

Most popular time to fly with an average 20% increase in price.

Flight from Anchorage 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.

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

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Complete your trip

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Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Alaska

First Class flights to Chicagofrom $1,329

Business Class flights to Chicagofrom $809

Premium Economy Class flights to Chicagofrom $2,209

Economy Class flights to Chicagofrom $281

$221 Find Cheap Flights from Alaska to Chicago - Compare and Save

Cheap Flights from Alaska to Chicago

Recent round-trip flight deals from Alaska to Chicago

Recent one-way flight deals from Alaska to Chicago

Recent last minute flight deals from Alaska to Chicago

Recent direct flight deals from Alaska to Chicago

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Alaska to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Alaska

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight