$180 Cheap Flights from Chicago (MDW) to Anchorage (ANC)

View $180 flight on Thu, Feb 19, 2026Opens in a new window

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

Cheap Flights from Chicago to Anchorage (MDW-ANC)

Prices were available within the past 7 days and start at $180 for one-way flights and $352 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Dec 28 - Mon, Dec 29
MDW
Chicago
ANC
Anchorage
$352 Roundtrip, found 13 hours ago
$352
Roundtrip
found 13 hours ago
Select Delta flight, departing Sun, Dec 28 from Chicago to Anchorage, returning Mon, Dec 29, priced at $352 found 13 hours ago
Delta
Sat, Nov 22 - Sun, Nov 30
MDW
Chicago
ANC
Anchorage
$358 Roundtrip, found 1 hour ago
$358
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Nov 22 from Chicago to Anchorage, returning Sun, Nov 30, priced at $358 found 1 hour ago
Delta
Sat, Nov 22 - Thu, Nov 27
MDW
Chicago
ANC
Anchorage
$359 Roundtrip, found 14 hours ago
$359
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, Nov 22 from Chicago to Anchorage, returning Thu, Nov 27, priced at $359 found 14 hours ago
Delta
Fri, Nov 21 - Wed, Nov 26
MDW
Chicago
ANC
Anchorage
$363 Roundtrip, found 18 hours ago
$363
Roundtrip
found 18 hours ago
Select Delta flight, departing Fri, Nov 21 from Chicago to Anchorage, returning Wed, Nov 26, priced at $363 found 18 hours ago
Delta
Sat, Nov 22 - Sun, Nov 30
MDW
Chicago
ANC
Anchorage
$364 Roundtrip, found 14 hours ago
$364
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, Nov 22 from Chicago to Anchorage, returning Sun, Nov 30, priced at $364 found 14 hours ago
Delta
Thu, Nov 27 - Thu, Dec 4
MDW
Chicago
ANC
Anchorage
$378 Roundtrip, found 3 days ago
$378
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 27 from Chicago to Anchorage, returning Thu, Dec 4, priced at $378 found 3 days ago
Delta
Fri, Nov 21 - Sun, Nov 23
MDW
Chicago
ANC
Anchorage
$383 Roundtrip, found 3 days ago
$383
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Nov 21 from Chicago to Anchorage, returning Sun, Nov 23, priced at $383 found 3 days ago
Delta
Wed, Dec 3 - Thu, Dec 4
MDW
Chicago
ANC
Anchorage
$384 Roundtrip, found 20 hours ago
$384
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Dec 3 from Chicago to Anchorage, returning Thu, Dec 4, priced at $384 found 20 hours ago
Delta
Sat, Dec 20 - Fri, Jan 2
MDW
Chicago
ANC
Anchorage
$390 Roundtrip, just found
$390
Roundtrip
just found
Select Delta flight, departing Sat, Dec 20 from Chicago to Anchorage, returning Fri, Jan 2, priced at $390 just found
Southwest Airlines
Wed, May 20 - Thu, May 28
MDW
Chicago
ANC
Anchorage
$797 Roundtrip, found 4 hours ago
$797
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Wed, May 20 from Chicago to Anchorage, returning Thu, May 28, priced at $797 found 4 hours ago

Alternative airports near Anchorage

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

Select flight to Ted Stevens Anchorage Intl. ANC. Cheapest option available. Average driving time to city center is 10 minutes. Flights from $358
ANC
Ted Stevens Anchorage Intl.
Cheapest
Average driving time to city center10 min
Flights from $358

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC) cost?
Lock in a cheap one-way flight from $180 or cheap return flight from $352 from Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC)?
December is the least expensive month to fly from MDW to ANC. Traveling during an off-peak travel window is often the key to scoring lower fares.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC)?
To find the cheapest airline flying from MDW to ANC, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC)?
You'll have to take a flight with a layover if you're traveling from Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC). 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 MDW to ANC?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC) route, travel before 3 PM. Departures after this time have a 22% higher chance of cancellation.**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 Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC) last-minute?
Holding off until just before your trip to book a flight from MDW to ANC generally means paying more. While you may come across some last-minute offers, they're not always guaranteed. Keep your travel schedule open to boost your chances of snagging a bargain.
Is it cheaper to book a MDW to ANC flight and hotel package?
You can save money by securing a MDW to ANC 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 it all in one place. After choosing your preferred accommodations and flights, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Ted Stevens Anchorage Intl. Airport (ANC)?
In most instances, you can modify or cancel your MDW to ANC flight. However, there may be additional charges, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like further details, head to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Ted Stevens Anchorage Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$352
Distance
2853 mi

Book with confidence

Chicago to Anchorage Flights

The cheapest times to fly from Chicago to Anchorage

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 Chicago to Anchorage are during the month of December. You can find some of the cheapest flights from Chicago to Anchorage with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Anchorage

Sunday is one of the best days to book for cheap flights from Chicago to Anchorage: 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 Chicago to Anchorage

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 Chicago to Anchorage in 2025. You can also book with separate airlines for your outbound and return journeys, from $180 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 Chicago to Anchorage 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 Chicago to Anchorage 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.

 

Chicago to Anchorage Flights

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*Available to One Key members.