What airlines fly to Chicago?

United Airlines, Alaska Airlines and Delta are the top three most popular airlines that fly to Chicago from Alaska according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Alaska to Chicago?

Alaska Airlines, Delta, and United Airlines are the most popular carriers operating from Alaska to Chicago

How long does it take to fly to Chicago?

Average flight duration from Alaska to Chicago depends on which airport you fly into and out of. Flying from Fairbanks to Chicago O'Hare Intl Airport is 6h 04m on average, while flying from Anchorage to Chicago O'Hare Intl Airport is 6h 07m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

When did momondo last update prices for flights from Alaska to Chicago?

Prices for flights from Alaska to Chicago were last updated today.

How many operators does momondo search for flights from Alaska to Chicago?

There are 5 operators available for flights from Alaska to Chicago as of January 2026.

How old do you have to be to fly from Alaska to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Alaska to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$160 Cheap Flights from Alaska to Chicago in 2026

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Find the cheapest flights from Alaska to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:24 pm - 8:40 am

ANC

ORD

6h 16mnonstop

7:20 am - 10:09 am

ORD

ANC

29h 49m

1 stop

$352Alaska Airlines

Thu, Jun 11 - Sat, Jun 13

6:00 am - 11:58 pm

ANC

ORD

14h 58m

1 stop

6:25 am - 6:46 pm

ORD

ANC

15h 21m

1 stop

$359Delta

Tue, Apr 14 - Sun, Apr 19

9:15 pm - 8:50 am

ANC

MDW

8h 35m

1 stop

9:30 am - 6:51 pm

MDW

ANC

12h 21m

1 stop

$359Delta

Wed, Mar 18 - Wed, Mar 25

1:34 am - 6:05 pm

ANC

ORD

13h 31m

2 stops

7:25 am - 2:45 pm

ORD

ANC

10h 20m

1 stop

$364Delta

Wed, Mar 18 - Mon, Mar 23

9:15 pm - 12:43 pm

ANC

MDW

12h 28m

2 stops

9:31 am - 6:46 pm

MDW

ANC

12h 15m

1 stop

$364Delta

Tue, Apr 14 - Mon, Apr 20

3:50 pm - 12:01 pm

ANC

ORD

17h 11m

2 stops

2:07 pm - 5:35 pm

ORD

ANC

30h 28m

1 stop

$367Alaska Airlines

Wed, Feb 18 - Mon, Feb 23

12:22 pm - 6:40 am

ANC

ORD

15h 18m

1 stop

8:20 am - 12:08 pm

ORD

ANC

6h 48mnonstop

$368Alaska Airlines

Thu, May 7 - Wed, May 13

1:34 am - 6:05 pm

ANC

ORD

13h 31m

2 stops

3:59 pm - 12:29 am

ORD

ANC

11h 30m

2 stops

$369Delta

Wed, Mar 18 - Mon, Mar 23

1:49 am - 7:03 pm

ANC

ORD

14h 14m

2 stops

8:20 am - 12:08 pm

ORD

ANC

6h 48mnonstop

$378Alaska Airlines

Wed, May 6 - Wed, May 13

12:55 am - 5:30 pm

ANC

ORD

13h 35m

1 stop

7:15 am - 8:07 pm

ORD

ANC

15h 52m

2 stops

$396Delta

Wed, Jun 10 - Sat, Jun 13

Delta flights from Alaska to Chicago

Our best Delta deals on Alaska to Chicago flight tickets

Delta

Apr 14

ANC9:15 pmAnchorage

8h 23m

1 stop

ORD8:38 amChicago O'Hare Intl

Apr 20

ORD8:50 amChicago O'Hare Intl

12h 56m

1 stop

ANC6:46 pmAnchorage

$359

Delta

Mar 18

ANC1:34 amAnchorage

13h 31m

2 stops

ORD6:05 pmChicago O'Hare Intl

Mar 23

ORD7:25 amChicago O'Hare Intl

10h 20m

1 stop

ANC2:45 pmAnchorage

$364

Delta

Mar 18

ANC1:34 amAnchorage

13h 31m

2 stops

ORD6:05 pmChicago O'Hare Intl

Mar 23

ORD3:59 pmChicago O'Hare Intl

11h 30m

2 stops

ANC12:29 amAnchorage

$369

Alaska Airlines flights from Alaska to Chicago

Our best Alaska Airlines deals on Alaska to Chicago flight tickets

Alaska Airlines

Jun 18

ANC11:24 pmAnchorage

6h 16m

ORD8:40 amChicago O'Hare Intl

Jun 24

ORD6:53 pmChicago O'Hare Intl

17h 54m

1 stop

ANC9:47 amAnchorage

$349

Alaska Airlines

Jun 11

ANC11:24 pmAnchorage

6h 16m

ORD8:40 amChicago O'Hare Intl

Jun 13

ORD7:20 amChicago O'Hare Intl

29h 49m

1 stop

ANC10:09 amAnchorage

$352

Alaska Airlines

Feb 18

ANC3:50 pmAnchorage

17h 11m

2 stops

ORD12:01 pmChicago O'Hare Intl

Feb 23

ORD2:07 pmChicago O'Hare Intl

30h 28m

1 stop

ANC5:35 pmAnchorage

$367

Fly from

Fly to

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 6/11

11:24 pm-8:40 am

Nonstop6h 16m

Chicago O'Hare Intl

Sat 6/13

7:20 am-10:09 am

1 stop29h 49m

$352

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/14

6:00 am-11:58 pm

1 stop14h 58m

Chicago O'Hare Intl

Sun 4/19

6:25 am-6:46 pm

1 stop15h 21m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 3/18

9:15 pm-8:50 am

1 stop8h 35m

Chicago Midway

Wed 3/25

9:30 am-6:51 pm

1 stop12h 21m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 3/18

1:34 am-6:05 pm

2 stops13h 31m

Chicago O'Hare Intl

Mon 3/23

7:25 am-2:45 pm

1 stop10h 20m

$364

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/14

9:15 pm-12:43 pm

2 stops12h 28m

Chicago Midway

Mon 4/20

9:31 am-6:46 pm

1 stop12h 15m

$364

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 2/18

3:50 pm-12:01 pm

2 stops17h 11m

Chicago O'Hare Intl

Mon 2/23

2:07 pm-5:35 pm

1 stop30h 28m

$367

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/7

12:22 pm-6:40 am

1 stop15h 18m

Chicago O'Hare Intl

Wed 5/13

8:20 am-12:08 pm

Nonstop6h 48m

$368

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 3/18

1:34 am-6:05 pm

2 stops13h 31m

Chicago O'Hare Intl

Mon 3/23

3:59 pm-12:29 am

2 stops11h 30m

$369

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 5/6

1:49 am-7:03 pm

2 stops14h 14m

Chicago O'Hare Intl

Wed 5/13

8:20 am-12:08 pm

Nonstop6h 48m

$378

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 6/10

12:55 am-5:30 pm

1 stop13h 35m

Chicago O'Hare Intl

Sat 6/13

7:15 am-8:07 pm

2 stops15h 52m

$396

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Alaska to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Alaska, with most prices found around $318. If you’re not able to fly to Chicago in October, then August is your next best option. Flight prices from Alaska to Chicago during August average around $367.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $637. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Alaska to Chicago for around $788.

What is the cheapest Alaska to Chicago flight route?

Fly from Anchorage to Chicago O'Hare Intl for the best Alaska - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Alaska when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $495 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Alaska for as low as $225 on momondo.

What cabin class options are available on Alaska to Chicago flights?

There are 4 cabin classes available to choose from on Alaska to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Alaska to Chicago flights?

No. A direct flight is the cheapest option for a flight between Alaska to Chicago.

Cheap Alaska to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Alaska to Chicago

Best Price Found	$299
Fastest flight time	6h 04m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Alaska in the past 72 hours is $299. The best round-trip flight deal from Alaska to Chicago found on momondo in the last 72 hours is $518.

The fastest flight from Alaska to Chicago takes 6h 04m

Direct flights go from Alaska to Chicago every day.

There are 3 airports in Chicago. From Alaska there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

When did momondo last update prices for flights from Alaska to Chicago?
Prices for flights from Alaska to Chicago were last updated today.
How many operators does momondo search for flights from Alaska to Chicago?
There are 5 operators available for flights from Alaska to Chicago as of January 2026.
How old do you have to be to fly from Alaska to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Alaska to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Alaska to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Alaska to Chicago is Boeing 737 MAX 8, representing 49.25% of all bookings. The subsequent popular models are Airbus A321neo at 14.93%, Boeing 737 MAX 9 at 7.46%, and Boeing 737 at 4.48%.

Best airlines flying from Alaska to Chicago

Compare and see reviews for airlines that fly from Alaska to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Hawaiian Airlines	PriceFrom $158	Free Cancellation	Rating 7.8 2,830 reviews	Search Hawaiian Airlines flights
Delta	PriceFrom $220	Free Cancellation	Rating 7.9 8,127 reviews	Search Delta flights
United Airlines	PriceFrom $254	Free Cancellation	Rating 7.4 9,215 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $318	Free Cancellation	Rating 8.0 11,808 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $338	Free Cancellation	Rating 7.2 11,206 reviews	Search American Airlines flights

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Hammond

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Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Alaska to Chicago?

Finding the right flight to Chicago from Alaska is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Alaska to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Alaska to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Alaska to Chicago?

Once all potential Alaska to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Alaska to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Alaska are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.