$134 Cheap Flights from Anchorage (ANC) to Chicago (MDW)

View $134 flight on Fri, Oct 17, 2025Opens in a new window

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

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Anchorage to Chicago (ANC-MDW)

Prices were available within the past 7 days and start at $134 for one-way flights and $270 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jan 2 - Tue, Jan 6
ANC
Anchorage
MDW
Chicago
$270 Roundtrip, found 1 day ago
$270
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 2 from Anchorage to Chicago, returning Tue, Jan 6, priced at $270 found 1 day ago
Delta
Fri, Jan 2 - Tue, Jan 6
ANC
Anchorage
MDW
Chicago
$330 Roundtrip, found 1 day ago
$330
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 2 from Anchorage to Chicago, returning Tue, Jan 6, priced at $330 found 1 day ago
Delta
Sat, Oct 18 - Sat, Oct 25
ANC
Anchorage
MDW
Chicago
$338 Roundtrip, found 6 days ago
$338
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Oct 18 from Anchorage to Chicago, returning Sat, Oct 25, priced at $338 found 6 days ago
Delta
Sat, Oct 11 - Tue, Oct 14
ANC
Anchorage
MDW
Chicago
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 11 from Anchorage to Chicago, returning Tue, Oct 14, priced at $344 found 1 day ago
Delta
Sat, Nov 1 - Sat, Nov 8
ANC
Anchorage
MDW
Chicago
$356 Roundtrip, found 17 hours ago
$356
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, Nov 1 from Anchorage to Chicago, returning Sat, Nov 8, priced at $356 found 17 hours ago
Delta
Sat, Oct 11 - Tue, Oct 14
ANC
Anchorage
MDW
Chicago
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 11 from Anchorage to Chicago, returning Tue, Oct 14, priced at $364 found 1 day ago
Delta
Fri, Oct 17 - Mon, Oct 20
ANC
Anchorage
MDW
Chicago
$366 Roundtrip, found 1 day ago
$366
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 17 from Anchorage to Chicago, returning Mon, Oct 20, priced at $366 found 1 day ago
Delta
Fri, Oct 3 - Mon, Oct 6
ANC
Anchorage
MDW
Chicago
$370 Roundtrip, found 6 days ago
$370
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Oct 3 from Anchorage to Chicago, returning Mon, Oct 6, priced at $370 found 6 days ago
Delta
Tue, Oct 21 - Wed, Oct 22
ANC
Anchorage
MDW
Chicago
$383 Roundtrip, found 1 day ago
$383
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 21 from Anchorage to Chicago, returning Wed, Oct 22, priced at $383 found 1 day ago
Delta
Sat, Nov 22 - Thu, Nov 27
ANC
Anchorage
MDW
Chicago
$387 Roundtrip, found 18 hours ago
$387
Roundtrip
found 18 hours ago
Select Delta flight, departing Sat, Nov 22 from Anchorage to Chicago, returning Thu, Nov 27, priced at $387 found 18 hours ago

Frequently asked questions

How much does a flight from Ted Stevens Anchorage Intl. Airport (ANC) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $134 or cheap return flight from $270 from Ted Stevens Anchorage Intl. Airport (ANC) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Ted Stevens Anchorage Intl. Airport (ANC) to Midway Intl. Airport (MDW)?
The cheapest month to fly from ANC to MDW is January, when there's less demand. Off-peak season is typically when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Ted Stevens Anchorage Intl. Airport (ANC) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest ANC to MDW flight.
How many flights per day from Ted Stevens Anchorage Intl. Airport (ANC) to Midway Intl. Airport (MDW)?
You'll need to book a flight with a layover when traveling from Ted Stevens Anchorage Intl. Airport (ANC) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from ANC to MDW?
Usually you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* But this can change depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Ted Stevens Anchorage Intl. Airport (ANC) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) without delays, pick a flight that leaves from Ted Stevens Anchorage Intl. Airport (ANC) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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 Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from ANC to MDW just before your trip is usually more expensive. However, if there's some wiggle room with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book an ANC to MDW flight and hotel package?
You'll generally save money by booking an ANC to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've selected your preferred accommodations and flights, you can add 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 Midway Intl. Airport (MDW)?
If you booked your ANC to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the fare 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 for more details.

Travel information

Travel information

Origin airport
Ted Stevens Anchorage Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$269
Distance
2853 mi

Book with confidence

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 January. 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 $134 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

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.