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Anchorage

$180+ Cheap flights from Midway (MDW) to Anchorage (ANC)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Find cheap flights from Midway to Anchorage with Cheapflights

1. Tell us where you want to go

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Cheap flight deals from Midway to Anchorage

Cheapest flights from Midway to Anchorage
Explore the most affordable flight options available from Midway to Anchorage. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/307:20 pm
MDW
-
ANC
2 stops20h 02m
Delta
Tue 3/319:15 pm
ANC
-
MDW
1 stop8h 35m
Delta
Deal found 1/25$358
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/19:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Fri 4/109:15 pm
ANC
-
MDW
1 stop13h 10m
Delta
Deal found 1/25$359
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:20 pm
MDW
-
ANC
1 stop26h 31m
Delta
Sun 4/129:15 pm
ANC
-
MDW
1 stop18h 21m
Delta
Deal found 1/25$360
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/19:35 am
MDW
-
ANC
2 stops29h 47m
Delta
Thu 4/99:15 pm
ANC
-
MDW
1 stop18h 25m
Delta
Deal found 1/25$364
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:31 am
MDW
-
ANC
1 stop12h 15m
Delta
Mon 4/203:45 pm
ANC
-
MDW
2 stops14h 02m
Delta
Deal found 1/26$366
This Delta deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/31:00 pm
MDW
-
ANC
2 stops15h 35m
Delta
Tue 7/75:15 pm
ANC
-
MDW
2 stops16h 52m
Delta
Deal found 1/24$371
This Delta deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:45 am
MDW
-
ANC
1 stop10h 12m
Delta
Sat 2/289:15 pm
ANC
-
MDW
1 stop12h 50m
Delta
Deal found 1/24$378
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:34 am
MDW
-
ANC
2 stops16h 07m
Delta
Tue 3/39:15 pm
ANC
-
MDW
1 stop12h 50m
Delta
Deal found 1/25$383
This Delta deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/29:30 am
MDW
-
ANC
2 stops18h 03m
Delta
Fri 7/1012:49 pm
ANC
-
MDW
1 stop16h 49m
Delta
Deal found 1/24$396
This Delta deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Wed 3/189:15 pm
ANC
-
MDW
1 stop13h 10m
Delta
Deal found 1/24$397
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:20 am
MDW
-
ANC
1 stop13h 07m
Delta
Sat 9/192:20 pm
ANC
-
MDW
2 stops15h 18m
Delta
Deal found 1/25$398

Find flight deals from Midway to Anchorage

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Anchorage (ANC). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(Delta)

One-way from

$180
(Delta)

Popular in

June

Cheapest in

October

Average price

$459
Provider with most accurate pricing for Chicago Midway-Anchorage flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Anchorage flights.
Search Deals
From Chicago Midway to Anchorage
Search Deals
One-way flight from Chicago Midway to Anchorage
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Anchorage that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Anchorage that are best for you.

Fly from

Midway

Fly to

Anchorage

Route

Depart

Return

Price

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 3/26

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Tue 3/31

9:15 pm-8:50 am

1 stop8h 35m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 4/2

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Sat 4/11

9:15 pm-6:40 pm

1 stop18h 25m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 4/16

9:26 am-6:46 pm

1 stop12h 20m

Anchorage

Mon 4/20

9:15 pm-8:46 am

1 stop8h 31m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 3/10

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Tue 3/17

9:15 pm-1:25 pm

1 stop13h 10m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 3/24

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Tue 3/31

9:15 pm-1:25 pm

1 stop13h 10m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 4/4

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Sat 4/11

9:15 pm-6:40 pm

1 stop18h 25m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 3/28

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Tue 3/31

9:15 pm-6:40 pm

1 stop18h 25m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 4/1

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Fri 4/10

9:15 pm-1:25 pm

1 stop13h 10m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 4/4

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Fri 4/10

9:15 pm-6:40 pm

1 stop18h 25m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 4/18

6:00 am-6:49 pm

1 stop15h 49m

Anchorage

Sat 4/25

8:25 pm-9:56 am

1 stop10h 31m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to Anchorage

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Anchorage in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Anchorage flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Anchorage flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Anchorage flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Anchorage flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Anchorage flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Anchorage

Have a flexible travel schedule? Discover the best time to fly to Anchorage from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Midway to Anchorage. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Anchorage from Chicago Midway?

    Most people fly into Anchorage (ANC) if they book a flight to Anchorage from Chicago Midway. On average, Anchorage has 0 inbound flights from Chicago Midway per day from 0 airlines. Anchorage is conveniently located just 4.4 mi from Anchorage’s city center.

  • How long is the flight from Chicago Midway Airport to Anchorage?

    Delta can get you from Chicago Midway Airport to Anchorage in just under 12h 21m. Your travel time can differ by up to . There are 2852 mi between Chicago Midway Airport and Anchorage.

  • Can I find deals for flights from Midway to Anchorage that include hotel bookings?

    Yes. In addition to deals on Midway to Anchorage flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Anchorage?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Anchorage.

  • Can I find deals for business class flights from Midway to Anchorage?

    Yes. Cheapflights offers flight deals from Midway to Anchorage by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Anchorage?

Book flights to Anchorage if you plan to visit one of these locations
Seward
Girdwood

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