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$170+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$332
(Delta)

One-way from

$170
(Delta)

Popular in

December

Cheapest in

April

Average price

$456
From Chicago Midway to Anchorage
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One-way flight from Chicago Midway to Anchorage
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Highest demand for flights based on searches. 0% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/9. 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 11/117:02 pmMDW - ANC
1 stop8h 54mDelta
Wed 11/126:05 amANC - MDW
1 stop9h 13mDelta
Deal found 9/9$332
This Delta deal was found by Cheapflights users on 9/9. 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 11/87:10 pmMDW - ANC
1 stop8h 41mDelta
Wed 11/126:05 amANC - MDW
1 stop9h 13mDelta
Deal found 9/9$338
This Delta deal was found by Cheapflights users on 9/11. 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 10/221:08 pmMDW - ANC
2 stops12h 35mDelta
Sat 10/258:15 pmANC - MDW
1 stop10h 25mDelta
Deal found 9/11$343
This Delta deal was found by Cheapflights users on 9/10. 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 10/31:43 pmMDW - ANC
1 stop8h 10mDelta
Mon 10/65:20 pmANC - MDW
2 stops12h 20mDelta
Deal found 9/10$344
This Delta deal was found by Cheapflights users on 9/11. 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 10/221:08 pmMDW - ANC
2 stops12h 35mDelta
Sun 10/265:20 pmANC - MDW
2 stops12h 20mDelta
Deal found 9/11$350
This Delta deal was found by Cheapflights users on 9/11. 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 10/157:10 pmMDW - ANC
1 stop8h 41mDelta
Sat 10/256:05 amANC - MDW
1 stop8h 38mDelta
Deal found 9/11$370
This Delta deal was found by Cheapflights users on 9/9. 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 10/29:20 amMDW - ANC
2 stops13h 59mDelta
Mon 10/66:05 amANC - MDW
1 stop8h 38mDelta
Deal found 9/9$375
This Delta deal was found by Cheapflights users on 9/10. 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 10/21:43 pmMDW - ANC
1 stop8h 10mDelta
Wed 10/85:20 pmANC - MDW
2 stops12h 35mDelta
Deal found 9/10$376
This Delta deal was found by Cheapflights users on 9/10. 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 10/11:08 pmMDW - ANC
2 stops15h 29mDelta
Tue 10/712:30 amANC - MDW
2 stops14h 55mDelta
Deal found 9/10$382

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 September 11, 2025.
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

Sat 10/4

11:00 am-6:56 pm

1 stop10h 56m

Anchorage

Sat 10/11

6:05 am-5:43 pm

1 stop8h 38m

$338

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 11/15

7:02 pm-12:56 am

1 stop8h 54m

Anchorage

Tue 12/9

6:05 am-6:18 pm

1 stop9h 13m

$338

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 10/27

7:10 pm-12:51 am

1 stop8h 41m

Anchorage

Wed 10/29

6:05 am-5:43 pm

1 stop8h 38m

$338

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 10/1

9:35 am-8:19 pm

2 stops13h 44m

Anchorage

Sat 10/4

6:15 am-5:35 pm

1 stop8h 20m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 10/22

1:08 pm-10:43 pm

2 stops12h 35m

Anchorage

Sun 10/26

6:05 am-5:43 pm

1 stop8h 38m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 11/5

1:08 pm-10:43 pm

2 stops12h 35m

Anchorage

Wed 11/12

6:05 am-6:18 pm

1 stop9h 13m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 10/15

1:08 pm-10:43 pm

2 stops12h 35m

Anchorage

Sat 10/25

6:05 am-5:43 pm

1 stop8h 38m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 10/22

1:08 pm-10:43 pm

2 stops12h 35m

Anchorage

Sat 10/25

9:45 pm-8:55 am

1 stop8h 10m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 11/8

6:00 am-6:31 pm

2 stops15h 31m

Anchorage

Wed 11/12

6:05 am-6:18 pm

1 stop9h 13m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 10/11

7:10 pm-12:51 am

1 stop8h 41m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 15 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Anchorage

What is the cheapest time of day to fly from MDW to ANC?

Find hourly flight availability from Midway to Anchorage. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Anchorage at noon. If you’re flexible enough to do this you can expect to save up to 57% on your trip compared to booking a flight in the afternoon.

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 10h 56m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Anchorage?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Anchorage (average of $456). Flying from Chicago Midway Airport to Anchorage in July is currently the most expensive (average of $642). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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