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

4 flights are operational daily from Anchorage to Chicago as of May 2026. The most popular departure time for this route is 8:00PM, with 100% of flights per day taking off in the evening.

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

The number of flights available between Anchorage and Chicago is 28 per week as of May 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

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

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

What airlines fly to Chicago?

United Airlines, Alaska Airlines and Delta are the top three most popular airlines that fly to Chicago from Anchorage according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 4 as of May 2026.

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.

$199 Cheap Flights from Anchorage to Chicago in 2026

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

Prices are currently low for flights on this route. Typical prices usually range from $597 to $414. The lowest price recently found on this route was $399.

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Find the cheapest flights from Anchorage to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:50 pm - 7:23 am

ANC

ORD

6h 33mnonstop

5:02 pm - 8:41 pm

ORD

ANC

6h 39mnonstop

$399American Airlines

Thu, Jun 4 - Mon, Jun 8

11:08 pm - 8:25 am

ANC

ORD

6h 17mnonstop

7:49 pm - 9:51 am

ORD

ANC

17h 02m

1 stop

$408Alaska Airlines

Fri, May 22 - Thu, May 28

11:08 pm - 8:25 am

ANC

ORD

6h 17mnonstop

3:28 pm - 9:36 pm

ORD

ANC

9h 08m

1 stop

$409Alaska Airlines

Mon, Jun 1 - Sat, Jun 6

11:08 pm - 8:25 am

ANC

ORD

6h 17mnonstop

8:05 am - 11:53 am

ORD

ANC

6h 48mnonstop

$418Alaska Airlines

Sat, May 23 - Tue, May 26

6:00 am - 6:01 pm

ANC

MDW

9h 01m

1 stop

1:27 pm - 8:56 pm

MDW

ANC

10h 29m

1 stop

$419Delta

Wed, Aug 26 - Sun, Aug 30

9:00 am - 10:59 pm

ANC

ORD

10h 59m

1 stop

5:52 pm - 12:46 am

ORD

ANC

9h 54m

1 stop

$419Alaska Airlines

Mon, Jun 1 - Sat, Jun 6

6:00 am - 6:01 pm

ANC

MDW

9h 01m

1 stop

1:27 pm - 11:24 pm

MDW

ANC

12h 57m

2 stops

$424Delta

Wed, Aug 26 - Sun, Aug 30

10:25 pm - 2:40 pm

ANC

MDW

13h 15m

2 stops

12:35 pm - 10:45 pm

MDW

ANC

13h 10m

2 stops

$429Southwest

Fri, May 22 - Thu, May 28

9:59 pm - 8:42 am

ANC

MDW

7h 43m

1 stop

9:23 am - 8:49 pm

MDW

ANC

14h 26m

1 stop

$448Delta

Fri, May 29 - Fri, Jun 5

12:55 am - 4:15 pm

ANC

MDW

12h 20m

2 stops

11:10 am - 11:45 pm

MDW

ANC

15h 35m

1 stop

$469Southwest

Thu, Sep 10 - Mon, Sep 14

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American Airlines flights from Anchorage to Chicago

Our best American Airlines deals on Anchorage to Chicago flight tickets

American Airlines

Jun 4

ANC9:50 pmAnchorage

6h 33m

ORD7:23 amChicago O'Hare Intl

Jun 8

ORD5:02 pmChicago O'Hare Intl

6h 39m

ANC8:41 pmAnchorage

$399

American Airlines

Jun 6

ANC9:50 pmAnchorage

6h 33m

ORD7:23 amChicago O'Hare Intl

Jun 8

ORD5:02 pmChicago O'Hare Intl

6h 39m

ANC8:41 pmAnchorage

$408

American Airlines

Jun 5

ANC11:42 pmAnchorage

10h 01m

1 stop

ORD12:43 pmChicago O'Hare Intl

Jun 8

ORD3:00 pmChicago O'Hare Intl

10h 35m

1 stop

ANC10:35 pmAnchorage

$464

Alaska Airlines flights from Anchorage to Chicago

Our best Alaska Airlines deals on Anchorage to Chicago flight tickets

Alaska Airlines

Jun 2

ANC11:08 pmAnchorage

6h 17m

ORD8:25 amChicago O'Hare Intl

Jun 6

ORD3:28 pmChicago O'Hare Intl

9h 08m

1 stop

ANC9:36 pmAnchorage

$409

Alaska Airlines

May 23

ANC11:08 pmAnchorage

6h 17m

ORD8:25 amChicago O'Hare Intl

May 26

ORD8:05 amChicago O'Hare Intl

6h 48m

ANC11:53 amAnchorage

$418

Alaska Airlines

May 26

ANC1:50 amAnchorage

19h 09m

1 stop

ORD11:59 pmChicago O'Hare Intl

Jun 6

ORD5:52 pmChicago O'Hare Intl

9h 54m

1 stop

ANC12:46 amAnchorage

$419

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 6/4

9:50 pm-7:23 am

Nonstop6h 33m

Chicago O'Hare Intl

Mon 6/8

5:02 pm-8:41 pm

Nonstop6h 39m

$399

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 5/22

11:08 pm-8:25 am

Nonstop6h 17m

Chicago O'Hare Intl

Thu 5/28

7:49 pm-9:51 am

1 stop17h 02m

$408

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 6/1

11:08 pm-8:25 am

Nonstop6h 17m

Chicago O'Hare Intl

Sat 6/6

3:28 pm-9:36 pm

1 stop9h 08m

$409

Quickest round-trip

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 5/23

11:08 pm-8:25 am

Nonstop6h 17m

Chicago O'Hare Intl

Tue 5/26

8:05 am-11:53 am

Nonstop6h 48m

$418

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 8/26

6:00 am-6:01 pm

1 stop9h 01m

Chicago Midway

Sun 8/30

1:27 pm-8:56 pm

1 stop10h 29m

$419

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 6/1

9:00 am-10:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Sat 6/6

5:52 pm-12:46 am

1 stop9h 54m

$419

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 8/26

6:00 am-6:01 pm

1 stop9h 01m

Chicago Midway

Sun 8/30

1:27 pm-11:24 pm

2 stops12h 57m

$424

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 5/22

10:25 pm-2:40 pm

2 stops13h 15m

Chicago Midway

Thu 5/28

12:35 pm-10:45 pm

2 stops13h 10m

$429

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 5/29

9:59 pm-8:42 am

1 stop7h 43m

Chicago Midway

Fri 6/5

9:23 am-8:49 pm

1 stop14h 26m

$448

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 9/10

12:55 am-4:15 pm

2 stops12h 20m

Chicago Midway

Mon 9/14

11:10 am-11:45 pm

1 stop15h 35m

$469

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

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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 October is, on average, the cheapest month to fly to Chicago from Anchorage, with most prices found around $158. If you’re not able to fly to Chicago in October, then August is your next best option. Flight prices from Anchorage to Chicago during August average around $158.

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 $653. 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 $794.

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 from Anchorage 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 $495 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 $313 on momondo.

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	$328
Fastest flight time	6h 10m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Anchorage in the past 72 hours is $328. The best round-trip flight deal from Anchorage to Chicago found on momondo in the last 72 hours is $573.

The fastest flight from Anchorage to Chicago takes 6h 10m

Direct flights go from Anchorage to Chicago every day.

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

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Frequently asked questions about flying from Anchorage to Chicago

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 10m.
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 4 as of May 2026.
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 69.60% of the total bookings. Other popular models include Airbus A321neo with 5.60%, Boeing 737 MAX 9 with 4.80%, and Boeing 737 with 4.80%.
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 (47% of total bookings). The next most popular airlines are United Airlines (36%) and Delta (16%).

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
United Airlines	PriceFrom $314	Free Cancellation	Rating 7.4 9,683 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $314	Free Cancellation	Rating 7.9 12,330 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $331	Free Cancellation	Rating 7.1 11,669 reviews	Search American Airlines flights
Delta	PriceFrom $337	Free Cancellation	Rating 7.9 8,460 reviews	Search Delta flights

United Airlines Flights From Anchorage to Chicago
United Airlines is one of the most popular airlines flying from Anchorage to Chicago, operating 14 flights/week on average for this route. A good United Airlines flight deal for Anchorage to Chicago starts from $314 round-trip, up to an average price of $542. Our users have rated United Airlines at 7.4/10.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

Monticello

Chesterton

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

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Cheap flights from Anchorage to Chicago from $199

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 6/28. 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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American Airlines flights from Anchorage to Chicago

Our best American Airlines deals on Anchorage to Chicago flight tickets

Alaska Airlines flights from Anchorage to Chicago

Our best Alaska Airlines deals on Anchorage to Chicago flight tickets

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How to get the cheapest flight ticket from Anchorage to Chicago

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

What is the cheapest month to fly to Chicago?

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

What is the cheapest Anchorage to Chicago flight route?

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

How have Anchorage to Chicago flight prices changed over time?

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

What airlines fly to Chicago?

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

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

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

Frequently asked questions about flying 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?

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

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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

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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