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

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

What airlines fly to Chicago?

Alaska Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Anchorage according to our data. Alaska Airlines is the first choice among our users, with 35% 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 Anchorage to Chicago on average per week?

The number of flights available between Anchorage and Chicago is 2 per week as of November 2025. The most frequent departure day is Sat, with 100% of weekly flights leaving on this day.

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

Prices for flights from Anchorage Airport to Chicago refresh daily.

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

The number of operators available for flights from Anchorage Airport to Chicago is 5 as of November 2025.

How old do you have to be to fly from Anchorage Airport 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 Anchorage Airport to Chicago.

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

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$176 Cheap Flights from Anchorage to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Anchorage and Chicago?

Prices are currently typical for flights on this route. Typical prices usually range from $318 to $569. The lowest price recently found on this route was $338.

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Find the cheapest flights from Anchorage to Chicago

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

2:10 am - 2:38 pmANC-ORD

9h 28m1 stop

8:00 am - 4:33 pmORD-ANC

11h 33m1 stop

$338Alaska Airlines

Find Deal

Mon, Jan 26 - Fri, Jan 30

12:38 am - 2:39 pmANC-ORD

11h 01m1 stop

8:00 am - 5:26 pmORD-ANC

12h 26m2 stops

$343Alaska Airlines

Find Deal

Thu, Dec 4 - Sun, Dec 7

4:00 pm - 5:00 amANC-ORD

10h 00m1 stop

7:00 am - 2:14 pmORD-ANC

10h 14m1 stop

$352Hawaiian Airlines

Find Deal

Tue, Apr 7 - Wed, Apr 8

8:55 am - 5:01 amANC-ORD

17h 06m1 stop

8:00 am - 11:44 pmORD-ANC

18h 44m1 stop

$353Alaska Airlines

Find Deal

Fri, Nov 28 - Sat, Dec 13

1:15 am - 1:20 pmANC-ORD

9h 05m1 stop

2:20 pm - 8:44 pmORD-ANC

9h 24m1 stop

$358Delta

Find Deal

Tue, Dec 23 - Wed, Jan 14

9:45 pm - 9:19 amANC-MDW

8h 34m1 stop

9:59 am - 7:04 pmMDW-ANC

12h 05m1 stop

$358Delta

Find Deal

Fri, Dec 5 - Sun, Dec 7

8:30 pm - 10:54 amANC-ORD

11h 24m1 stop

7:36 am - 6:58 pmORD-ANC

14h 22m1 stop

$448American Airlines

Find Deal

Fri, Dec 26 - Thu, Jan 1

1:04 am - 5:38 pmANC-ORD

13h 34m1 stop

7:36 am - 6:58 pmORD-ANC

14h 22m1 stop

$498American Airlines

Find Deal

Thu, Dec 25 - Thu, Jan 1

8:55 pm - 6:13 amANC-ORD

6h 18mnonstop

4:05 pm - 7:45 pmORD-ANC

6h 40mnonstop

$518United Airlines

Find Deal

Wed, Apr 8 - Tue, Apr 14

9:07 pm - 6:09 amANC-ORD

6h 02mnonstop

4:05 pm - 7:59 pmORD-ANC

6h 54mnonstop

$559United Airlines

Find Deal

Sat, Nov 22 - Fri, Nov 28

Alaska Airlines flights from Anchorage to Chicago

Our best Alaska Airlines deals on Anchorage to Chicago flight tickets

Alaska Airlines

Jan 26

ANC2:10 amAnchorage

9h 28m

1 stop

ORD2:38 pmChicago O'Hare Intl

Jan 30

ORD8:00 amChicago O'Hare Intl

11h 33m

1 stop

ANC4:33 pmAnchorage

$338

Find similar

Alaska Airlines

Dec 4

ANC12:38 amAnchorage

11h 01m

1 stop

ORD2:39 pmChicago O'Hare Intl

Dec 7

ORD8:00 amChicago O'Hare Intl

12h 26m

2 stops

ANC5:26 pmAnchorage

$343

Find similar

Alaska Airlines

Nov 28

ANC8:55 amAnchorage

17h 06m

1 stop

ORD5:01 amChicago O'Hare Intl

Dec 13

ORD8:00 amChicago O'Hare Intl

18h 44m

1 stop

ANC11:44 pmAnchorage

$353

Find similar

Delta flights from Anchorage to Chicago

Our best Delta deals on Anchorage to Chicago flight tickets

Delta

Dec 23

ANC1:15 amAnchorage

9h 05m

1 stop

ORD1:20 pmChicago O'Hare Intl

Jan 14

ORD2:20 pmChicago O'Hare Intl

9h 24m

1 stop

ANC8:44 pmAnchorage

$358

Find similar

Delta

Dec 24

ANC5:45 amAnchorage

12h 51m

2 stops

ORD9:36 pmChicago O'Hare Intl

Jan 15

ORD2:20 pmChicago O'Hare Intl

9h 24m

1 stop

ANC8:44 pmAnchorage

$363

Find similar

Delta

Jan 13

ANC9:15 pmAnchorage

12h 52m

2 stops

ORD1:07 pmChicago O'Hare Intl

Feb 8

ORD1:58 pmChicago O'Hare Intl

13h 52m

2 stops

ANC12:50 amAnchorage

$368

Find similar

Fly from

Fly to

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 1/26

2:10 am-2:38 pm

1 stop9h 28m

Chicago O'Hare Intl

Fri 1/30

8:00 am-4:33 pm

1 stop11h 33m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 12/4

12:38 am-2:39 pm

1 stop11h 01m

Chicago O'Hare Intl

Sun 12/7

8:00 am-5:26 pm

2 stops12h 26m

$343

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/7

4:00 pm-5:00 am

1 stop10h 00m

Chicago O'Hare Intl

Wed 4/8

7:00 am-2:14 pm

1 stop10h 14m

$352

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 11/28

8:55 am-5:01 am

1 stop17h 06m

Chicago O'Hare Intl

Sat 12/13

8:00 am-11:44 pm

1 stop18h 44m

$353

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 12/23

1:15 am-1:20 pm

1 stop9h 05m

Chicago O'Hare Intl

Wed 1/14

2:20 pm-8:44 pm

1 stop9h 24m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 12/5

9:45 pm-9:19 am

1 stop8h 34m

Chicago Midway

Sun 12/7

9:59 am-7:04 pm

1 stop12h 05m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 12/26

8:30 pm-10:54 am

1 stop11h 24m

Chicago O'Hare Intl

Thu 1/1

7:36 am-6:58 pm

1 stop14h 22m

$448

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 12/25

1:04 am-5:38 pm

1 stop13h 34m

Chicago O'Hare Intl

Thu 1/1

7:36 am-6:58 pm

1 stop14h 22m

$498

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 4/8

8:55 pm-6:13 am

Nonstop6h 18m

Chicago O'Hare Intl

Tue 4/14

4:05 pm-7:45 pm

Nonstop6h 40m

$518

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 11/22

9:07 pm-6:09 am

Nonstop6h 02m

Chicago O'Hare Intl

Fri 11/28

4:05 pm-7:59 pm

Nonstop6h 54m

$559

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 Anchorage 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 typical price of a round-trip flight between Anchorage and Chicago?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Anchorage, with most prices found around $395. If you’re not able to fly to Chicago in November, then September is your next best option. Flight prices from Anchorage to Chicago during September average around $396.

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 Sunday, the most expensive travel day of the week, you can expect to see flight prices from Anchorage to Chicago for around $833.

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 Anchorage 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 $705.

What is the cheapest Anchorage to Chicago flight route?

Fly from Anchorage to Chicago O'Hare Intl for the best Anchorage - 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 Anchorage when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $488 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Anchorage for as low as $225 on momondo.

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

There are 4 cabin classes available to choose from on Anchorage 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 Anchorage to Chicago flights?

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

How have Anchorage to Chicago flight prices changed over time?

When to book flights from Anchorage to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Anchorage to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Anchorage to Chicago (ANC to CHI) flight deals and tips

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

Best Price Found	$279
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 Anchorage in the past 72 hours is $279. The best round-trip flight deal from Anchorage to Chicago found on momondo in the last 72 hours is $442.

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

Direct flights go from Anchorage to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Anchorage to Chicago by plane?
The straight-line distance from Anchorage to Chicago is 2848.0 mi. By plane, this route typically takes 6h 02m.
When did momondo last update prices for flights from Anchorage Airport to Chicago?
Prices for flights from Anchorage Airport to Chicago refresh daily.
How many operators does momondo search for flights from Anchorage Airport to Chicago?
The number of operators available for flights from Anchorage Airport to Chicago is 5 as of November 2025.
How old do you have to be to fly from Anchorage Airport 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 Anchorage Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Anchorage to Chicago?
Based on momondo bookings for flights between Anchorage and Chicago, the leading plane model is Boeing 737 MAX 8, making up 45.05% of the total bookings. Other popular models include Airbus A321neo with 17.58%, Boeing 737-900 Passenger/BBJ3 (winglets) with 13.74%, and Boeing 737 MAX 9 with 6.59%.
What is the most popular airline from Anchorage to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Anchorage to Chicago is Alaska Airlines (42% of total bookings). The next most popular airlines are United Airlines (30%), Delta (22%), and Hawaiian Airlines (6%).

Best airlines flying from Anchorage to Chicago

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

Airline	Rating	Free Cancellation	Price
Hawaiian Airlines	PriceFrom $187	Free Cancellation	Rating 7.8 2,799 reviews	Search Hawaiian Airlines flights
United Airlines	PriceFrom $254	Free Cancellation	Rating 7.4 8,994 reviews	Search United Airlines flights
Delta	PriceFrom $259	Free Cancellation	Rating 7.9 7,997 reviews	Search Delta flights
Alaska Airlines	PriceFrom $318	Free Cancellation	Rating 8.0 11,232 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $338	Free Cancellation	Rating 7.2 11,033 reviews	Search American Airlines flights

United Airlines Flights From Anchorage to Chicago
United Airlines is one of the most popular airlines flying from Anchorage to Chicago, operating 1 flight/week on average for this route. A good United Airlines flight deal for Anchorage to Chicago starts from $254 round-trip, up to an average price of $482. Our users have rated United Airlines at 7.4/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

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 Anchorage to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Anchorage.

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

momondo does allow users to show only those flights to Chicago from Anchorage which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Anchorage.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Anchorage and alert you when they 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.

Start using Trips

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Mon 12/1

Mon 12/8

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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

Popular cities in the United States

Flights to New Yorkfrom $49

Flights to Los Angelesfrom $47

Flights to Miamifrom $47

Flights to Orlandofrom $47

Flights to Las Vegasfrom $39

Flights to San Franciscofrom $39

Flights to Washington, D.C.from $40

Flights to Bostonfrom $60

Flights to Atlantafrom $47

Flights to Dallasfrom $49

Flights to Seattlefrom $53

Flights to Denverfrom $47

Cheap flights from Anchorage to Chicago from $176

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Anchorage to Chicago departing on 11/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Anchorage to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

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Alaska Airlines flights from Anchorage to Chicago

Our best Alaska Airlines deals on Anchorage to Chicago flight tickets

Delta flights from Anchorage to Chicago

Our best Delta deals on Anchorage to Chicago flight tickets

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Anchorage 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 typical price of a round-trip flight between Anchorage and Chicago?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Anchorage, with most prices found around $395. If you’re not able to fly to Chicago in November, then September is your next best option. Flight prices from Anchorage to Chicago during September average around $396.

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 Anchorage 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 $705.

What is the cheapest Anchorage to Chicago flight route?

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

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

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

There are 4 cabin classes available to choose from on Anchorage 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 Anchorage to Chicago flights?

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

How have Anchorage to Chicago flight prices changed over time?

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

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

What airlines fly to Chicago?

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

The number of flights available between Anchorage and Chicago is 2 per week as of November 2025. The most frequent departure day is Sat, with 100% of weekly flights leaving on this day.

When to book flights from Anchorage to Chicago

Cheap Anchorage to Chicago (ANC to CHI) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Anchorage to Chicago by plane?

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

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

How old do you have to be to fly from Anchorage Airport to Chicago?

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

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

What is the most popular airline from Anchorage to Chicago?

Best airlines flying from Anchorage to Chicago

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

United Airlines Flights From Anchorage to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

I’m not ready to book a flight from Anchorage 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