$208 Cheap Flights from Anchorage (ANC) to Chicago (MDW)

View $208 flight on Sun, Jun 7, 2026Opens in a new window

Popular airlines from Ted Stevens Anchorage Intl. Airport (ANC) to Chicago Midway Airport (MDW)

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Cheap Flights from Anchorage to Chicago (ANC-MDW)

Prices were available within the past 7 days and start at $208 for one-way flights and $417 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Apr 25 - Tue, Apr 28
ANC
Anchorage
MDW
Chicago
$417 Roundtrip, found 2 days ago
$417
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Apr 25 from Anchorage to Chicago, returning Tue, Apr 28, priced at $417 found 2 days ago
Delta
Tue, Apr 21 - Sat, Apr 25
ANC
Anchorage
MDW
Chicago
$418 Roundtrip, found 4 days ago
$418
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Apr 21 from Anchorage to Chicago, returning Sat, Apr 25, priced at $418 found 4 days ago
Southwest Airlines
Fri, May 15 - Thu, Jun 4
ANC
Anchorage
MDW
Chicago
$423 Roundtrip, found 6 days ago
$423
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, May 15 from Anchorage to Chicago, returning Thu, Jun 4, priced at $423 found 6 days ago
Southwest Airlines
Fri, May 15 - Thu, Jun 4
ANC
Anchorage
MDW
Chicago
$428 Roundtrip, found 6 days ago
$428
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, May 15 from Anchorage to Chicago, returning Thu, Jun 4, priced at $428 found 6 days ago
Delta
Mon, May 25 - Tue, May 26
ANC
Anchorage
MDW
Chicago
$430 Roundtrip, found 1 day ago
$430
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, May 25 from Anchorage to Chicago, returning Tue, May 26, priced at $430 found 1 day ago
Delta
Mon, Jun 1 - Sat, Jun 6
ANC
Anchorage
MDW
Chicago
$434 Roundtrip, found 4 days ago
$434
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Jun 1 from Anchorage to Chicago, returning Sat, Jun 6, priced at $434 found 4 days ago
Delta
Tue, Jun 16 - Sun, Jun 28
ANC
Anchorage
MDW
Chicago
$456 Roundtrip, found 9 hours ago
$456
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jun 16 from Anchorage to Chicago, returning Sun, Jun 28, priced at $456 found 9 hours ago
Delta
Sat, May 23 - Sun, May 24
ANC
Anchorage
MDW
Chicago
$457 Roundtrip, found 1 day ago
$457
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 23 from Anchorage to Chicago, returning Sun, May 24, priced at $457 found 1 day ago
Delta
Tue, Jun 23 - Wed, Jun 24
ANC
Anchorage
MDW
Chicago
$459 Roundtrip, found 4 days ago
$459
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jun 23 from Anchorage to Chicago, returning Wed, Jun 24, priced at $459 found 4 days ago
Southwest Airlines
Wed, Aug 19 - Thu, Aug 20
ANC
Anchorage
MDW
Chicago
$466 Roundtrip, found 11 hours ago
$466
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, Aug 19 from Anchorage to Chicago, returning Thu, Aug 20, priced at $466 found 11 hours ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $741
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $741

Frequently asked questions

How much does a flight from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $208 and cheap return flights from $417 Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $395 and $1349. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from ANC to MDW is April when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter ANC to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
Delta and United are just some of the carriers that fly from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.). Use Expedia's flight search tool to compare airlines on this route and find our cheapest option for your trip. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Anchorage, Alaska (ANC) to Chicago, Illinois (MDW) usually leaves at around 1:05 AM, operated by Delta. This is a seasonal service active in March, giving you an early start to your travels. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
a Saturday typically has the most flights from Ted Stevens Anchorage Intl. (ANC) to Midway Intl. (MDW), with approximately 6 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Delta and United.
What are the most popular departure times for flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Anchorage (ANC) to Chicago (MDW) are in the late evening, from 9pm to midnight. About 44% of passengers prefer this time window. Delta Air Lines and United Airlines both offer flights during this window. This timing is favored as it allows you to enjoy a full day in Anchorage before your flight.
How long does it take to fly from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flights from ANC to MDW with one stop typically take around 9 hours, covering approximately 2,854 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the ANC to MDW route with Delta Air Lines.
How do I earn miles on a Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Ted Stevens Anchorage Intl. (ANC)?
When traveling from Ted Stevens Anchorage Intl. (ANC) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Seattle - Tacoma Intl. (SEA), San Francisco Intl. (SFO), George Bush Intercontinental (IAH) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Ted Stevens Anchorage Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$416
Distance
2853 mi

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 April. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $208 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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