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Cheap flights from Anchorage to Chicago from $159

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 10/11. 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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Cheap round-trip flights

United Airlines Logo
9:04 pm - 6:13 amANC-ORD
6h 09mnonstop
United Airlines Logo
4:10 pm - 7:57 pmORD-ANC
6h 47mnonstop
$318United Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 20
United Airlines Logo
9:04 pm - 6:13 amANC-ORD
6h 09mnonstop
United Airlines Logo
2:53 pm - 10:42 pmORD-ANC
10h 49m1 stop
$328United Airlines
Find Deal
Thu, Oct 9 - Tue, Oct 14
Alaska Airlines Logo
11:11 pm - 8:40 amANC-ORD
6h 29mnonstop
Alaska Airlines Logo
6:00 am - 5:27 pmORD-ANC
14h 27m1 stop
$337Alaska Airlines
Find Deal
Sat, Oct 11 - Tue, Oct 14
Hawaiian Airlines Logo
1:15 am - 1:04 pmANC-ORD
8h 49m1 stop
Hawaiian Airlines Logo
7:45 am - 4:17 pmORD-ANC
11h 32m1 stop
$338Hawaiian Airlines
Find Deal
Mon, Jan 12 - Sun, Feb 8
Alaska Airlines Logo
1:47 am - 5:01 amANC-ORD
24h 14m1 stop
Alaska Airlines Logo
8:20 am - 12:18 pmORD-ANC
6h 58mnonstop
$340Alaska Airlines
Find Deal
Thu, Oct 9 - Sat, Oct 18
Alaska Airlines Logo
7:05 am - 12:24 amANC-ORD
14h 19m1 stop
Alaska Airlines Logo
2:05 pm - 10:48 pmORD-ANC
11h 43m2 stops
$343Alaska Airlines
Find Deal
Wed, Nov 5 - Mon, Nov 17
Alaska Airlines Logo
5:35 pm - 12:24 amANC-ORD
27h 49m1 stop
Alaska Airlines Logo
7:00 am - 12:49 amORD-ANC
20h 49m2 stops
$346Alaska Airlines
Find Deal
Tue, Nov 4 - Mon, Nov 10
Alaska Airlines Logo
1:04 am - 4:30 pmANC-ORD
12h 26m1 stop
Alaska Airlines Logo
6:00 am - 7:32 pmORD-ANC
16h 32m1 stop
$347Alaska Airlines
Find Deal
Mon, Nov 17 - Fri, Nov 28
Delta Logo
12:30 am - 1:30 pmANC-ORD
10h 00m1 stop
Delta Logo
7:37 am - 4:22 pmORD-ANC
11h 45m1 stop
$356Delta
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Tue, Oct 21 - Sun, Oct 26
Delta Logo
6:05 am - 5:43 pmANC-MDW
8h 38m1 stop
Delta Logo
7:10 pm - 12:51 amMDW-ANC
8h 41m1 stop
$356Delta
Find Deal
Thu, Oct 9 - Mon, Oct 13

Alaska Airlines flights from Anchorage to Chicago

Our best Alaska Airlines deals on Anchorage to Chicago flight tickets
Alaska Airlines
Oct 11
ANC11:11 pmAnchorage
6h 29m
ORD8:40 amChicago O'Hare Intl
Oct 14
ORD6:00 amChicago O'Hare Intl
14h 27m
1 stop
ANC5:27 pmAnchorage
$337
Find similar
Alaska Airlines
Oct 9
ANC1:47 amAnchorage
24h 14m
1 stop
ORD5:01 amChicago O'Hare Intl
Oct 18
ORD8:20 amChicago O'Hare Intl
6h 58m
ANC12:18 pmAnchorage
$340
Find similar
Alaska Airlines
Nov 5
ANC7:05 amAnchorage
14h 19m
1 stop
ORD12:24 amChicago O'Hare Intl
Nov 17
ORD2:05 pmChicago O'Hare Intl
11h 43m
2 stops
ANC10:48 pmAnchorage
$343
Find similar

United Airlines flights from Anchorage to Chicago

Our best United Airlines deals on Anchorage to Chicago flight tickets
United Airlines
Oct 15
ANC9:04 pmAnchorage
6h 09m
ORD6:13 amChicago O'Hare Intl
Oct 20
ORD4:10 pmChicago O'Hare Intl
6h 47m
ANC7:57 pmAnchorage
$318
Find similar
United Airlines
Oct 9
ANC9:04 pmAnchorage
6h 09m
ORD6:13 amChicago O'Hare Intl
Oct 14
ORD2:53 pmChicago O'Hare Intl
10h 49m
1 stop
ANC10:42 pmAnchorage
$328
Find similar
United Airlines
Oct 10
ANC11:49 pmAnchorage
8h 39m
1 stop
ORD11:28 amChicago O'Hare Intl
Oct 18
ORD4:10 pmChicago O'Hare Intl
6h 47m
ANC7:57 pmAnchorage
$366
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 September 16, 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

Wed 10/15

9:04 pm-6:13 am

Nonstop6h 09m

Chicago O'Hare Intl

Mon 10/20

4:10 pm-7:57 pm

Nonstop6h 47m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/9

9:04 pm-6:13 am

Nonstop6h 09m

Chicago O'Hare Intl

Tue 10/14

2:53 pm-10:42 pm

1 stop10h 49m

$328

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 10/11

11:11 pm-8:40 am

Nonstop6h 29m

Chicago O'Hare Intl

Tue 10/14

6:00 am-5:27 pm

1 stop14h 27m

$337

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 1/12

1:15 am-1:04 pm

1 stop8h 49m

Chicago O'Hare Intl

Sun 2/8

7:45 am-4:17 pm

1 stop11h 32m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/9

1:47 am-5:01 am

1 stop24h 14m

Chicago O'Hare Intl

Sat 10/18

8:20 am-12:18 pm

Nonstop6h 58m

$340

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 11/5

7:05 am-12:24 am

1 stop14h 19m

Chicago O'Hare Intl

Mon 11/17

2:05 pm-10:48 pm

2 stops11h 43m

$343

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 11/4

5:35 pm-12:24 am

1 stop27h 49m

Chicago O'Hare Intl

Mon 11/10

7:00 am-12:49 am

2 stops20h 49m

$346

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 11/17

1:04 am-4:30 pm

1 stop12h 26m

Chicago O'Hare Intl

Fri 11/28

6:00 am-7:32 pm

1 stop16h 32m

$347

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 10/21

12:30 am-1:30 pm

1 stop10h 00m

Chicago O'Hare Intl

Sun 10/26

7:37 am-4:22 pm

1 stop11h 45m

$356

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 10/9

6:05 am-5:43 pm

1 stop8h 38m

Chicago Midway

Mon 10/13

7:10 pm-12:51 am

1 stop8h 41m

$356

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 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 $398.

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 $660. 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 $850.

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 $729.

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 $482 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 $377 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

$210

Fastest flight time

6h 02m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Anchorage in the past 72 hours is $210. The best round-trip flight deal from Anchorage to Chicago found on momondo in the last 72 hours is $405.
The fastest flight from Anchorage to Chicago takes 6h 02m
Direct flights go from Anchorage to Chicago every day.
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 09m.

  • 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
2,724 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $254Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $328Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
DeltaPriceFrom $337Free CancellationRating
7.9
7,957 reviews
Search Delta flights
American AirlinesPriceFrom $338Free CancellationRating
7.2
10,000 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 14 flights/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 $499. Our users have rated United Airlines at 7.4/10.

  • American Airlines Flights From Anchorage to Chicago

    $338 is the best American Airlines flight deal from Anchorage to Chicago found on momondo over the last 72 hours. The average American Airlines ticket price found was closer to $574, however, with flight time and availability significantly affecting the price. American Airlines (7.2/10 from 10,000 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
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 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