$159 Cheap Flights from Anchorage (ANC) to Chicago (ORD)

View $159 flight on Tue, Aug 19, 2025Opens 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 $159 for one-way flights and $313 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, Sep 11 - Fri, Sep 12
ANC
Anchorage
ORD
Chicago
$313 Roundtrip, just found
$313
Roundtrip
just found
Select United flight, departing Thu, Sep 11 from Anchorage to Chicago, returning Fri, Sep 12, priced at $313 just found
Alaska Airlines
Tue, Aug 19 - Wed, Aug 20
ANC
Anchorage
ORD
Chicago
$313 Roundtrip, found 1 day ago
$313
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Aug 19 from Anchorage to Chicago, returning Wed, Aug 20, priced at $313 found 1 day ago
American Airlines
Thu, Sep 18 - Fri, Sep 19
ANC
Anchorage
ORD
Chicago
$313 Roundtrip, just found
$313
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Anchorage to Chicago, returning Fri, Sep 19, priced at $313 just found
United
Mon, Sep 22 - Wed, Oct 1
ANC
Anchorage
ORD
Chicago
$318 Roundtrip, just found
$318
Roundtrip
just found
Select United flight, departing Mon, Sep 22 from Anchorage to Chicago, returning Wed, Oct 1, priced at $318 just found
United
Sun, Oct 12 - Sun, Oct 19
ANC
Anchorage
ORD
Chicago
$321 Roundtrip, found 20 hours ago
$321
Roundtrip
found 20 hours ago
Select United flight, departing Sun, Oct 12 from Anchorage to Chicago, returning Sun, Oct 19, priced at $321 found 20 hours ago
United
Thu, Sep 11 - Fri, Sep 12
ANC
Anchorage
ORD
Chicago
$322 Roundtrip, just found
$322
Roundtrip
just found
Select United flight, departing Thu, Sep 11 from Anchorage to Chicago, returning Fri, Sep 12, priced at $322 just found
Alaska Airlines
Mon, Aug 25 - Mon, Sep 1
ANC
Anchorage
ORD
Chicago
$324 Roundtrip, just found
$324
Roundtrip
just found
Select Alaska Airlines flight, departing Mon, Aug 25 from Anchorage to Chicago, returning Mon, Sep 1, priced at $324 just found
United
Sun, Aug 24 - Mon, Aug 25
ANC
Anchorage
ORD
Chicago
$325 Roundtrip, found 18 hours ago
$325
Roundtrip
found 18 hours ago
Select United flight, departing Sun, Aug 24 from Anchorage to Chicago, returning Mon, Aug 25, priced at $325 found 18 hours ago
Delta
Mon, Sep 22 - Wed, Oct 1
ANC
Anchorage
ORD
Chicago
$333 Roundtrip, just found
$333
Roundtrip
just found
Select Delta flight, departing Mon, Sep 22 from Anchorage to Chicago, returning Wed, Oct 1, priced at $333 just found
Hawaiian Airlines
Fri, Aug 15 - Sat, Aug 30
ANC
Anchorage
ORD
Chicago
$348 Roundtrip, found 4 days ago
$348
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Fri, Aug 15 from Anchorage to Chicago, returning Sat, Aug 30, priced at $348 found 4 days ago

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

April is typically the cheapest month to fly

From $319 - $630 per traveler.

Graph displaying average flight prices per month

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 $538
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $538
Flights from Anchorage (ANC) to Chicago (ORD)
Origin airport
Ted Stevens Anchorage Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Hawaiian Airlines, United
Roundtrip price
$312
Distance
2838 mi
Average flight time
9 hours 17 mins

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 September. 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 $159 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.

 

Frequently asked questions

How much does a flight from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD) cost?
Grab cheap return fares starting at $315 from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ANC on August 15 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from ANC to ORD?
The cheapest flights from ANC to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ANC to ORD?
With fares starting at $159 for a one-way journey from ANC to ORD, United is currently the cheapest carrier on this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ANC on October 18 2025. Prices were last updated on July 23 2025 and have not changed since.
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.

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*Available to One Key members.