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Cheap flights from Anchorage to Chicago from $177

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 1/13. 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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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
4:54 pm - 2:38 pm
ANC
-
ORD
18h 44m1 stop
Alaska Airlines Logo
5:29 pm - 1:09 am
ORD
-
ANC
10h 40m1 stop
$356Alaska Airlines
Fri, Feb 6 - Sun, Feb 15
Alaska Airlines Logo
12:49 am - 1:10 pm
ANC
-
ORD
9h 21m1 stop
Alaska Airlines Logo
7:00 am - 9:49 pm
ORD
-
ANC
17h 49m1 stop
$357Alaska Airlines
Mon, Feb 2 - Mon, Feb 16
Delta Logo
9:15 pm - 1:06 pm
ANC
-
MDW
12h 51m1 stop
Delta Logo
9:50 am - 6:57 pm
MDW
-
ANC
12h 07m1 stop
$358Delta
Tue, Feb 3 - Tue, Feb 17
Alaska Airlines Logo
12:49 am - 1:10 pm
ANC
-
ORD
9h 21m1 stop
Alaska Airlines Logo
3:54 pm - 1:11 am
ORD
-
ANC
12h 17m1 stop
$358Alaska Airlines
Sun, Feb 8 - Mon, Feb 16
Delta Logo
6:10 am - 8:40 am
ANC
-
ORD
23h 30m1 stop
Delta Logo
7:30 am - 12:09 am
ORD
-
ANC
19h 39m1 stop
$359Delta
Thu, Jan 15 - Mon, Jan 19
Delta Logo
6:10 am - 9:05 pm
ANC
-
ORD
11h 55m2 stops
Delta Logo
8:50 am - 6:56 pm
ORD
-
ANC
13h 06m1 stop
$363Delta
Tue, Jan 13 - Sun, Feb 8
Delta Logo
6:10 am - 6:32 pm
ANC
-
MDW
9h 22m1 stop
Delta Logo
9:32 am - 6:56 pm
MDW
-
ANC
12h 24m2 stops
$363Delta
Wed, Jan 14 - Wed, Jan 21
Delta Logo
6:10 am - 9:05 pm
ANC
-
ORD
11h 55m2 stops
Delta Logo
8:50 am - 10:18 pm
ORD
-
ANC
16h 28m2 stops
$368Delta
Tue, Jan 13 - Sun, Feb 8
Delta Logo
1:30 pm - 8:52 am
ANC
-
MDW
16h 22m2 stops
Delta Logo
9:32 am - 6:56 pm
MDW
-
ANC
12h 24m2 stops
$368Delta
Wed, Jan 14 - Wed, Jan 21
Delta Logo
6:10 am - 9:43 pm
ANC
-
ORD
12h 33m1 stop
Delta Logo
8:50 am - 6:56 pm
ORD
-
ANC
13h 06m1 stop
$390Delta
Thu, Jan 15 - Thu, Jan 22

Delta flights from Anchorage to Chicago

Our best Delta deals on Anchorage to Chicago flight tickets
Delta
Feb 3
ANC9:15 pmAnchorage
8h 53m
1 stop
MDW9:08 amChicago Midway
Feb 12
MDW9:50 amChicago Midway
12h 07m
1 stop
ANC6:57 pmAnchorage
$358
Find similar
Delta
Jan 15
ANC6:10 amAnchorage
23h 30m
1 stop
ORD8:40 amChicago O'Hare Intl
Jan 19
ORD7:30 amChicago O'Hare Intl
19h 39m
1 stop
ANC12:09 amAnchorage
$359
Find similar
Delta
Jan 13
ANC6:10 amAnchorage
11h 55m
2 stops
ORD9:05 pmChicago O'Hare Intl
Feb 8
ORD8:50 amChicago O'Hare Intl
13h 06m
1 stop
ANC6:56 pmAnchorage
$363
Find similar

United Airlines flights from Anchorage to Chicago

Our best United Airlines deals on Anchorage to Chicago flight tickets
United Airlines
Dec 25
ANC9:00 pmAnchorage
6h 24m
ORD6:24 amChicago O'Hare Intl
Dec 31
ORD8:50 amChicago O'Hare Intl
18h 35m
2 stops
ANC12:25 amAnchorage
$730
Find similar
United Airlines
Dec 24
ANC9:00 pmAnchorage
6h 24m
ORD6:24 amChicago O'Hare Intl
Dec 27
ORD3:58 pmChicago O'Hare Intl
6h 47m
ANC7:45 pmAnchorage
$770
Find similar
United Airlines
Dec 24
ANC9:00 pmAnchorage
6h 24m
ORD6:24 amChicago O'Hare Intl
Dec 31
ORD2:31 pmChicago O'Hare Intl
11h 25m
1 stop
ANC10:56 pmAnchorage
$780
Find similar

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 December 18, 2025.
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

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 2/6

4:54 pm-2:38 pm

1 stop18h 44m

Chicago O'Hare Intl

Sun 2/15

5:29 pm-1:09 am

1 stop10h 40m

$356

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 2/2

12:49 am-1:10 pm

1 stop9h 21m

Chicago O'Hare Intl

Mon 2/16

7:00 am-9:49 pm

1 stop17h 49m

$357

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 2/3

9:15 pm-1:06 pm

1 stop12h 51m

Chicago Midway

Tue 2/17

9:50 am-6:57 pm

1 stop12h 07m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 2/8

12:49 am-1:10 pm

1 stop9h 21m

Chicago O'Hare Intl

Mon 2/16

3:54 pm-1:11 am

1 stop12h 17m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 1/15

6:10 am-8:40 am

1 stop23h 30m

Chicago O'Hare Intl

Mon 1/19

7:30 am-12:09 am

1 stop19h 39m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 1/13

6:10 am-9:05 pm

2 stops11h 55m

Chicago O'Hare Intl

Sun 2/8

8:50 am-6:56 pm

1 stop13h 06m

$363

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 1/14

6:10 am-6:32 pm

1 stop9h 22m

Chicago Midway

Wed 1/21

9:32 am-6:56 pm

2 stops12h 24m

$363

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 1/13

6:10 am-9:05 pm

2 stops11h 55m

Chicago O'Hare Intl

Sun 2/8

8:50 am-10:18 pm

2 stops16h 28m

$368

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 1/14

1:30 pm-8:52 am

2 stops16h 22m

Chicago Midway

Wed 1/21

9:32 am-6:56 pm

2 stops12h 24m

$368

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 1/15

6:10 am-9:43 pm

1 stop12h 33m

Chicago O'Hare Intl

Thu 1/22

8:50 am-6:56 pm

1 stop13h 06m

$390

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 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 $318. If you’re not able to fly to Chicago in October, then November is your next best option. Flight prices from Anchorage to Chicago during November average around $395.

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 $646. 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 $806.

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 $701.

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 $496 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

$298

Fastest flight time

6h 07m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Anchorage in the past 72 hours is $298. The best round-trip flight deal from Anchorage to Chicago found on momondo in the last 72 hours is $776.
The fastest flight from Anchorage to Chicago takes 6h 07m
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

  • 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 07m.

  • 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
Hawaiian AirlinesPriceFrom $187Free CancellationRating
7.8
2,820 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $259Free CancellationRating
7.9
8,005 reviews
Search Delta flights
United AirlinesPriceFrom $314Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $318Free CancellationRating
8.0
11,477 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $338Free CancellationRating
7.2
11,054 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 7 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 $496. Our users have rated United Airlines at 7.4/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
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

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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