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Cheap flights from Anchorage to Chicago from $211

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 9/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Anchorage to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
10:28 pm - 7:40 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 12mnonstop
Alaska Airlines Logo
7:20 am - 11:12 amORD  Chicago O'Hare Intl-ANC Anchorage
6h 52mnonstop
$423Alaska Airlines
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
9:54 pm - 7:25 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 31mnonstop
American Airlines Logo
4:53 pm - 8:49 pmORD  Chicago O'Hare Intl-ANC Anchorage
6h 56mnonstop
$423American Airlines
Thu, Sep 17 - Wed, Sep 23
United Airlines Logo
8:59 pm - 6:10 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 11mnonstop
United Airlines Logo
4:05 pm - 7:57 pmORD  Chicago O'Hare Intl-ANC Anchorage
6h 52mnonstop
$423United Airlines
Thu, Oct 1 - Mon, Oct 5
United Airlines Logo
8:59 pm - 6:10 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 11mnonstop
United Airlines Logo
4:05 pm - 7:57 pmORD  Chicago O'Hare Intl-ANC Anchorage
6h 52mnonstop
$423United Airlines
Thu, Oct 1 - Tue, Oct 6
American Airlines Logo
9:54 pm - 7:25 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 31mnonstop
American Airlines Logo
4:53 pm - 8:49 pmORD  Chicago O'Hare Intl-ANC Anchorage
6h 56mnonstop
$424American Airlines
Thu, Sep 17 - Wed, Sep 23
Alaska Airlines Logo
10:28 pm - 7:40 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 12mnonstop
Alaska Airlines Logo
8:00 am - 12:47 amORD  Chicago O'Hare Intl-ANC Anchorage
19h 47m1 stop Seattle/Tacoma Intl
$428Alaska Airlines
Thu, Sep 3 - Wed, Sep 9
Alaska Airlines Logo
10:28 pm - 7:40 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 12mnonstop
Alaska Airlines Logo
7:20 am - 11:12 amORD  Chicago O'Hare Intl-ANC Anchorage
6h 52mnonstop
$441Alaska Airlines
Tue, Sep 1 - Mon, Sep 7
Delta Logo
6:00 am - 6:19 pmANC  Anchorage-MDW Chicago Midway
9h 19m1 stop Minneapolis St Paul
Delta Logo
10:01 am - 8:59 pmMDW  Chicago Midway-ANC Anchorage
13h 58m1 stop Minneapolis St Paul
$443Delta
Thu, Oct 1 - Wed, Oct 7
Delta Logo
10:10 pm - 1:20 pmANC  Anchorage-MDW Chicago Midway
12h 10m1 stop Minneapolis St Paul
Delta Logo
7:13 pm - 12:45 amMDW  Chicago Midway-ANC Anchorage
8h 32m1 stop Minneapolis St Paul
$443Delta
Fri, Oct 2 - Mon, Oct 5
Multiple Airlines Logo
12:55 pm - 11:05 amANC  Anchorage-ORD Chicago O'Hare Intl
43h 10m2 stops Seattle/Tacoma Intl Toronto Pearson Intl
Multiple Airlines Logo
8:52 pm - 11:08 amORD  Chicago O'Hare Intl-ANC Anchorage
17h 16m1 stop Seattle/Tacoma Intl
$2,642Multiple Airlines
Thu, Nov 26 - Sat, Nov 28

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Alaska Airlines flights from Anchorage to Chicago

Our best Alaska Airlines deals on Anchorage to Chicago flight tickets
Alaska Airlines
Sep 3
ANC10:28 pmAnchorage
6h 12m
ORD7:40 amChicago O'Hare Intl
Sep 9
ORD8:00 amChicago O'Hare Intl
19h 47m
1 stop
ANC12:47 amAnchorage
$428
Alaska Airlines
Feb 2
ANC7:15 amAnchorage
9h 40m
1 stop
ORD7:55 pmChicago O'Hare Intl
Feb 6
ORD8:00 amChicago O'Hare Intl
14h 10m
1 stop
ANC7:10 pmAnchorage
$463
Alaska Airlines
Feb 2
ANC6:00 amAnchorage
10h 55m
1 stop
ORD7:55 pmChicago O'Hare Intl
Feb 6
ORD2:03 pmChicago O'Hare Intl
13h 07m
2 stops
ANC12:10 amAnchorage
$468

United Airlines flights from Anchorage to Chicago

Our best United Airlines deals on Anchorage to Chicago flight tickets
United Airlines
Oct 1
ANC8:59 pmAnchorage
6h 11m
ORD6:10 amChicago O'Hare Intl
Oct 5
ORD4:05 pmChicago O'Hare Intl
6h 52m
ANC7:57 pmAnchorage
$423
United Airlines
Oct 1
ANC8:59 pmAnchorage
6h 11m
ORD6:10 amChicago O'Hare Intl
Oct 5
ORD1:30 pmChicago O'Hare Intl
12h 13m
1 stop
ANC10:43 pmAnchorage
$433
United Airlines
Sep 3
ANC9:20 pmAnchorage
6h 12m
ORD6:32 amChicago O'Hare Intl
Sep 7
ORD4:05 pmChicago O'Hare Intl
6h 54m
ANC7:59 pmAnchorage
$441

momondo Fare Finder

 
Customize your flight search to find flights from Anchorage to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 9, 2026.
Use the filters below to find and compare flights from Anchorage to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AnchorageChicago

ANC Anchorage - ORD Chicago O'Hare Intl

ANCORD

Anchorage

Thu 9/3

10:28 pm-7:40 am

Nonstop6h 12m

Chicago O'Hare Intl

Mon 9/7

7:20 am-11:12 am

Nonstop6h 52m

$423

AnchorageChicago

ANC Anchorage - ORD Chicago O'Hare Intl

ANCORD

Anchorage

Thu 9/17

9:54 pm-7:25 am

Nonstop6h 31m

Chicago O'Hare Intl

Wed 9/23

4:53 pm-8:49 pm

Nonstop6h 56m

$423
Quickest round-trip

AnchorageChicago

ANC Anchorage - ORD Chicago O'Hare Intl

ANCORD

Anchorage

Thu 10/1

8:59 pm-6:10 am

Nonstop6h 11m

Chicago O'Hare Intl

Mon 10/5

4:05 pm-7:57 pm

Nonstop6h 52m

$423

AnchorageChicago

ANC Anchorage - ORD Chicago O'Hare Intl

ANCORD

Anchorage

Thu 10/1

8:59 pm-6:10 am

Nonstop6h 11m

Chicago O'Hare Intl

Tue 10/6

4:05 pm-7:57 pm

Nonstop6h 52m

$423

AnchorageChicago

ANC Anchorage - ORD Chicago O'Hare Intl

ANCORD

Anchorage

Thu 9/17

9:54 pm-7:25 am

Nonstop6h 31m

Chicago O'Hare Intl

Wed 9/23

4:53 pm-8:49 pm

Nonstop6h 56m

$424

AnchorageChicago

ANC Anchorage - ORD Chicago O'Hare Intl

ANCORD

Anchorage

Thu 9/3

10:28 pm-7:40 am

Nonstop6h 12m

Chicago O'Hare Intl

Wed 9/9

8:00 am-12:47 am

1 stop19h 47m

$428

AnchorageChicago

ANC Anchorage - ORD Chicago O'Hare Intl

ANCORD

Anchorage

Tue 9/1

10:28 pm-7:40 am

Nonstop6h 12m

Chicago O'Hare Intl

Mon 9/7

7:20 am-11:12 am

Nonstop6h 52m

$441

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Thu 10/1

6:00 am-6:19 pm

1 stop9h 19m

Chicago Midway

Wed 10/7

10:01 am-8:59 pm

1 stop13h 58m

$443

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Fri 10/2

10:10 pm-1:20 pm

1 stop12h 10m

Chicago Midway

Mon 10/5

7:13 pm-12:45 am

1 stop8h 32m

$443

AnchorageChicago

ANC Anchorage - ORD Chicago O'Hare Intl

ANCORD

Anchorage

Thu 11/26

12:55 pm-11:05 am

2 stops43h 10m

Chicago O'Hare Intl

Sat 11/28

8:52 pm-11:08 am

1 stop17h 16m

$2,642

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Anchorage, with most prices found around $358. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Anchorage to Chicago during November average around $387.

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 Thursday when prices can be found for as low as $646. 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 Anchorage to Chicago for around $778.

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 $520 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 $348 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.

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

$292

Fastest flight time

6h 11m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Anchorage in the past 72 hours is $292. The best round-trip flight deal from Anchorage to Chicago found on momondo in the last 72 hours is $503.
The fastest flight from Anchorage to Chicago takes 6h 11m
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).
Search flight deals

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 11m.

  • 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $204Free CancellationRating
7.9
12,786 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $314Free CancellationRating
7.4
10,089 reviews
Search United Airlines flights
American AirlinesPriceFrom $318Free CancellationRating
7.1
11,892 reviews
Search American Airlines flights
DeltaPriceFrom $337Free CancellationRating
7.8
8,499 reviews
Search Delta flights

  • Alaska Airlines Flights From Anchorage to Chicago

    Alaska Airlines is one of the most popular airlines flying from Anchorage to Chicago, operating 12 flights/week on average for this route. A good Alaska Airlines flight deal for Anchorage to Chicago starts from $204 round-trip, up to an average price of $529. Our users have rated Alaska Airlines at 7.9/10.

  • United Airlines Flights From Anchorage to Chicago

    $314 is the best United Airlines flight deal from Anchorage to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $537, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 10,089 user reviews) flies into Chicago from Anchorage 7 times in an average week so prices can vary.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport