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

United Airlines, Alaska Airlines, and Delta 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 Anchorage to Chicago O'Hare Intl Airport is 6h 02m on average, while flying from Fairbanks to Chicago O'Hare Intl Airport is 11h 25m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What airlines fly to Chicago?

Alaska Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Alaska according to our data. Alaska 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.

How many flights depart from Alaska to Chicago on average per week?

As of October 2025, 11 flights take off from Alaska and land in Chicago each week. The most common flight departure day for this route is Thu, with 45% of weekly flights taking off on this day.

How many flights depart from Alaska to Chicago on average per day?

As of October 2025, there are 1 flights per day flying from Alaska to Chicago. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.

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 October 2025.

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.

$173 Cheap Flights from Alaska to Chicago in 2025/26

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Find the cheapest flights from Alaska to Chicago

Round-trip

One-way

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Cheap round-trip flights

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7:05 am - 9:40 pmANC-ORD

11h 35m1 stop

8:00 am - 4:35 pmORD-ANC

11h 35m1 stop

$338Alaska Airlines

Find Deal

Thu, Nov 13 - Wed, Nov 19

5:24 pm - 6:21 amANC-ORD

9h 57m1 stop

8:00 am - 5:26 pmORD-ANC

12h 26m2 stops

$343Alaska Airlines

Find Deal

Wed, Dec 3 - Sat, Dec 6

2:35 pm - 5:00 amANC-ORD

11h 25m1 stop

7:00 am - 1:20 pmORD-ANC

9h 20m1 stop

$352Hawaiian Airlines

Find Deal

Tue, Apr 7 - Wed, Apr 8

6:05 am - 4:52 pmANC-ORD

7h 47m1 stop

7:47 am - 4:42 pmORD-ANC

11h 55m1 stop

$358Delta

Find Deal

Tue, Nov 18 - Fri, Nov 28

9:45 pm - 9:19 amANC-MDW

8h 34m1 stop

7:02 pm - 12:57 amMDW-ANC

8h 55m1 stop

$358Delta

Find Deal

Wed, Dec 3 - Fri, Dec 12

9:05 am - 9:40 pmANC-ORD

9h 35m1 stop

8:00 am - 5:32 pmORD-ANC

12h 32m2 stops

$360Multiple Airlines

Find Deal

Thu, Nov 13 - Wed, Nov 19

12:30 am - 3:02 pmANC-ORD

11h 32m2 stops

7:47 am - 4:42 pmORD-ANC

11h 55m1 stop

$363Delta

Find Deal

Mon, Nov 17 - Fri, Nov 28

12:30 am - 6:08 pmANC-MDW

14h 38m2 stops

9:41 am - 6:46 pmMDW-ANC

12h 05m1 stop

$363Delta

Find Deal

Wed, Nov 19 - Thu, Nov 27

9:07 pm - 6:09 amANC-ORD

6h 02mnonstop

4:05 pm - 7:59 pmORD-ANC

6h 54mnonstop

$392United Airlines

Find Deal

Tue, Nov 11 - Sun, Nov 16

9:07 pm - 6:09 amANC-ORD

6h 02mnonstop

4:05 pm - 7:59 pmORD-ANC

6h 54mnonstop

$472United Airlines

Find Deal

Thu, Nov 13 - Wed, Nov 19

United Airlines flights from Alaska to Chicago

Our best United Airlines deals on Alaska to Chicago flight tickets

United Airlines

Nov 11

ANC9:07 pmAnchorage

6h 02m

ORD6:09 amChicago O'Hare Intl

Nov 16

ORD4:05 pmChicago O'Hare Intl

6h 54m

ANC7:59 pmAnchorage

$392

Find similar

United Airlines

Nov 13

ANC9:07 pmAnchorage

6h 02m

ORD6:09 amChicago O'Hare Intl

Nov 19

ORD4:05 pmChicago O'Hare Intl

6h 54m

ANC7:59 pmAnchorage

$472

Find similar

United Airlines

Nov 13

ANC9:07 pmAnchorage

6h 02m

ORD6:09 amChicago O'Hare Intl

Nov 19

ORD1:55 pmChicago O'Hare Intl

12h 01m

1 stop

ANC10:56 pmAnchorage

$482

Find similar

Delta flights from Alaska to Chicago

Our best Delta deals on Alaska to Chicago flight tickets

Delta

Nov 18

ANC6:05 amAnchorage

7h 47m

1 stop

ORD4:52 pmChicago O'Hare Intl

Nov 28

ORD7:47 amChicago O'Hare Intl

11h 55m

1 stop

ANC4:42 pmAnchorage

$358

Find similar

Delta

Nov 17

ANC12:30 amAnchorage

11h 32m

2 stops

ORD3:02 pmChicago O'Hare Intl

Nov 28

ORD7:47 amChicago O'Hare Intl

11h 55m

1 stop

ANC4:42 pmAnchorage

$363

Find similar

Delta

Dec 6

ANC12:30 amAnchorage

12h 52m

2 stops

ORD4:22 pmChicago O'Hare Intl

Dec 14

ORD6:00 amChicago O'Hare Intl

13h 34m

2 stops

ANC4:34 pmAnchorage

$368

Find similar

Fly from

Fly to

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 11/13

7:05 am-9:40 pm

1 stop11h 35m

Chicago O'Hare Intl

Wed 11/19

8:00 am-4:35 pm

1 stop11h 35m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 12/3

5:24 pm-6:21 am

1 stop9h 57m

Chicago O'Hare Intl

Sat 12/6

8:00 am-5:26 pm

2 stops12h 26m

$343

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/7

2:35 pm-5:00 am

1 stop11h 25m

Chicago O'Hare Intl

Wed 4/8

7:00 am-1:20 pm

1 stop9h 20m

$352

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 11/18

6:05 am-4:52 pm

1 stop7h 47m

Chicago O'Hare Intl

Fri 11/28

7:47 am-4:42 pm

1 stop11h 55m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 12/3

9:45 pm-9:19 am

1 stop8h 34m

Chicago Midway

Fri 12/12

7:02 pm-12:57 am

1 stop8h 55m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 11/13

9:05 am-9:40 pm

1 stop9h 35m

Chicago O'Hare Intl

Wed 11/19

8:00 am-5:32 pm

2 stops12h 32m

$360

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 11/17

12:30 am-3:02 pm

2 stops11h 32m

Chicago O'Hare Intl

Fri 11/28

7:47 am-4:42 pm

1 stop11h 55m

$363

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 11/19

12:30 am-6:08 pm

2 stops14h 38m

Chicago Midway

Thu 11/27

9:41 am-6:46 pm

1 stop12h 05m

$363

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 11/11

9:07 pm-6:09 am

Nonstop6h 02m

Chicago O'Hare Intl

Sun 11/16

4:05 pm-7:59 pm

Nonstop6h 54m

$392

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 11/13

9:07 pm-6:09 am

Nonstop6h 02m

Chicago O'Hare Intl

Wed 11/19

4:05 pm-7:59 pm

Nonstop6h 54m

$472

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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 $358. If you’re not able to fly to Chicago in October, then November is your next best option. Flight prices from Alaska to Chicago during November average around $368.

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 $645. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Alaska to Chicago for around $830.

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Alaska to Chicago during this time can be as low as $331. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $712.

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 $486 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	$293
Fastest flight time	6h 02m
Direct flights	Mon, Wed, Thu, Fri, Sat and Sun
Airports in Chicago	1 airport

The best one-way flight to Chicago from Alaska in the past 72 hours is $293. The best round-trip flight deal from Alaska to Chicago found on momondo in the last 72 hours is $396.

The fastest flight from Alaska to Chicago takes 6h 02m

Direct flights go from Alaska to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.

There is 1 airport near Chicago: 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 October 2025.
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 40.74% of all bookings. The subsequent popular models are Airbus A321neo at 19.58%, Boeing 737-900 Passenger/BBJ3 (winglets) at 13.76%, and Boeing 737 MAX 9 at 8.47%.

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 $187	Free Cancellation	Rating 7.8 2,789 reviews	Search Hawaiian Airlines flights
United Airlines	PriceFrom $254	Free Cancellation	Rating 7.4 8,995 reviews	Search United Airlines flights
Delta	PriceFrom $259	Free Cancellation	Rating 7.9 7,982 reviews	Search Delta flights
Alaska Airlines	PriceFrom $318	Free Cancellation	Rating 8.0 11,161 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $338	Free Cancellation	Rating 7.2 11,033 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Sat 11/29

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Cheap flights from Alaska to Chicago from $173

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Alaska to Chicago departing on 11/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Alaska to Chicago

Cheap round-trip flights

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Cheap last minute flights

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United Airlines flights from Alaska to Chicago

Our best United Airlines deals on Alaska to Chicago flight tickets

Delta flights from Alaska to Chicago

Our best Delta deals on Alaska to Chicago flight tickets

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Use the filters below to find and compare flights from Alaska to Chicago that are best for you.

See travel insights to Chicago from

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

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 $358. If you’re not able to fly to Chicago in October, then November is your next best option. Flight prices from Alaska to Chicago during November average around $368.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Alaska to Chicago during this time can be as low as $331. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $712.

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?

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.

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

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

What airlines fly to Chicago?

How many flights depart from Alaska to Chicago on average per day?

As of October 2025, there are 1 flights per day flying from Alaska to Chicago. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.

How many flights depart from Alaska to Chicago on average per week?

As of October 2025, 11 flights take off from Alaska and land in Chicago each week. The most common flight departure day for this route is Thu, with 45% of weekly flights taking off on this day.

How long does it take to fly 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

Fastest flight time

Direct flights

Airports in Chicago

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

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

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

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

What is the most popular plane model from Alaska to Chicago?

Best airlines flying from Alaska to Chicago

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

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago