$169 Cheap Flights from Anchorage (ANC) to Chicago (ORD)

View $169 flight on Mon, May 25, 2026Opens in a new window

Popular airlines from Ted Stevens Anchorage Intl. Airport (ANC) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Anchorage to Chicago (ANC-ORD)

Prices were available within the past 7 days and start at $169 for one-way flights and $338 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, Nov 19 - Tue, Nov 25
ANC
Anchorage
ORD
Chicago
$338 Roundtrip, found 3 days ago
$338
Roundtrip
found 3 days ago
Select United flight, departing Wed, Nov 19 from Anchorage to Chicago, returning Tue, Nov 25, priced at $338 found 3 days ago
Alaska Airlines
Sat, Apr 25 - Sun, May 3
ANC
Anchorage
ORD
Chicago
$341 Roundtrip, found 5 days ago
$341
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sat, Apr 25 from Anchorage to Chicago, returning Sun, May 3, priced at $341 found 5 days ago
Alaska Airlines
Tue, Jun 30 - Wed, Jul 1
ANC
Anchorage
ORD
Chicago
$342 Roundtrip, found 3 hours ago
$342
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Tue, Jun 30 from Anchorage to Chicago, returning Wed, Jul 1, priced at $342 found 3 hours ago
Alaska Airlines
Tue, Jun 30 - Wed, Jul 1
ANC
Anchorage
ORD
Chicago
$348 Roundtrip, found 3 hours ago
$348
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Tue, Jun 30 from Anchorage to Chicago, returning Wed, Jul 1, priced at $348 found 3 hours ago
Alaska Airlines
Mon, May 18 - Tue, May 26
ANC
Anchorage
ORD
Chicago
$351 Roundtrip, found 14 hours ago
$351
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Mon, May 18 from Anchorage to Chicago, returning Tue, May 26, priced at $351 found 14 hours ago
Alaska Airlines
Tue, Nov 18 - Tue, Nov 25
ANC
Anchorage
ORD
Chicago
$353 Roundtrip, found 3 days ago
$353
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Nov 18 from Anchorage to Chicago, returning Tue, Nov 25, priced at $353 found 3 days ago
United
Fri, Feb 20 - Mon, Feb 23
ANC
Anchorage
ORD
Chicago
$357 Roundtrip, found 3 days ago
$357
Roundtrip
found 3 days ago
Select United flight, departing Fri, Feb 20 from Anchorage to Chicago, returning Mon, Feb 23, priced at $357 found 3 days ago
Delta
Tue, Dec 16 - Wed, Dec 24
ANC
Anchorage
ORD
Chicago
$358 Roundtrip, just found
$358
Roundtrip
just found
Select Delta flight, departing Tue, Dec 16 from Anchorage to Chicago, returning Wed, Dec 24, priced at $358 just found
American Airlines
Thu, Aug 20 - Fri, Aug 21
ANC
Anchorage
ORD
Chicago
$413 Roundtrip, found 14 hours ago
$413
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Thu, Aug 20 from Anchorage to Chicago, returning Fri, Aug 21, priced at $413 found 14 hours ago
Southwest Airlines
Sat, Jul 25 - Sat, Aug 1
ANC
Anchorage
ORD
Chicago
$891 Roundtrip, found 5 hours ago
$891
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Jul 25 from Anchorage to Chicago, returning Sat, Aug 1, priced at $891 found 5 hours ago

Find the cheapest month to fly from Anchorage (ANC) to Chicago (ORD)

September is typically the cheapest month to fly

From $312 - $462 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $544
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $544

Frequently asked questions

How much does a flight from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $169 or cheap return flight from $338 from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD)?
November is the cheapest month to fly from ANC to ORD. Traveling during an off-peak travel window is often the key to finding a great deal.
What is the cheapest airline that flies from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline that'll fly you from ANC to ORD, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD)?
There aren't any daily direct flights available from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD). But you can book flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from ANC to ORD?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can vary depending on various factors, including the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from ANC to ORD?
With 80% of flights generally landing on schedule, United Airlines has the best on-time performance for nonstop flights from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD). To check your flight status and get notifications about any changes, use the Expedia App.
What is the best time to fly from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Departures after this hour have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from ANC to ORD are usually more expensive. For the lowest rates, start searching for flights as early as possible. That being said, if your travel plans are flexible, it's possible to land a cheap ticket right before your journey.
Is it cheaper to book an ANC to ORD flight and hotel package?
You'll typically save money by booking an ANC to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After selecting your preferred accommodations and flights, consider adding extras such as tours, activities and car rentals.
Can I cancel or change the date of my flight from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD)?
If you booked your ANC to ORD flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Ted Stevens Anchorage Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Hawaiian Airlines, Southwest Airlines, United
Roundtrip price
$338
Distance
2838 mi
Average flight time
8 hours 32 mins

Book with confidence

Anchorage to Chicago Flights

The cheapest times to fly from Anchorage to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Anchorage to Chicago are during the month of November. You can find some of the cheapest flights from Anchorage to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Anchorage to Chicago

Sunday is one of the best days to book for cheap flights from Anchorage to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Anchorage to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Anchorage to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $169 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Anchorage to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Anchorage to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Anchorage to Chicago Flights

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