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$180+ Cheap flights from Midway (MDW) to Alaska

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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Midway to Alaska

Keep the following information in mind while searching for Midway to Alaska flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$358
(Delta)

One-way from

$180
(Delta)

Popular in

December

Cheapest in

April

Average price

$492
Provider with most accurate pricing for Chicago (CHI)-Anchorage flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Anchorage flights.
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From Chicago Midway to Alaska
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One-way flight from Chicago Midway to Alaska
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Midway to Alaska

Cheapest flights from Midway to Alaska
Explore the most affordable flight options available from Midway to Alaska. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 11/269:41 amMDW - ANC
1 stop12h 05mDelta
Wed 12/39:45 pmANC - MDW
1 stop8h 34mDelta
Deal found 10/27$358
This Delta deal was found by Cheapflights users on 10/27. 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 11/211:47 pmMDW - ANC
2 stops15h 10mDelta
Mon 11/246:05 amANC - MDW
1 stop9h 13mDelta
Deal found 10/27$363
This Delta deal was found by Cheapflights users on 10/28. 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 12/61:50 pmMDW - ANC
1 stop14h 07mDelta
Thu 12/251:44 pmANC - MDW
2 stops16h 05mDelta
Deal found 10/28$384
This Delta deal was found by Cheapflights users on 10/26. 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.
Sat 12/69:59 amMDW - FAI
2 stops17h 19mDelta
Fri 12/121:30 amFAI - MDW
2 stops13h 48mDelta
Deal found 10/26$392
This Delta deal was found by Cheapflights users on 10/28. 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 11/249:41 amMDW - ANC
1 stop12h 05mDelta
Thu 11/2712:30 amANC - MDW
2 stops14h 48mDelta
Deal found 10/28$429
This Delta deal was found by Cheapflights users on 10/27. 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 12/265:59 pmMDW - ANC
1 stop10h 23mDelta
Wed 1/76:10 amANC - MDW
1 stop9h 22mDelta
Deal found 10/27$470
This Delta deal was found by Cheapflights users on 10/29. 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 11/289:34 amMDW - ANC
2 stops16h 11mDelta
Sun 11/309:45 pmANC - MDW
1 stop8h 16mDelta
Deal found 10/29$485
This Delta deal was found by Cheapflights users on 10/28. 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 12/2611:48 amMDW - ANC
2 stops15h 11mDelta
Sun 1/49:15 pmANC - MDW
1 stop12h 54mDelta
Deal found 10/28$495
This Delta deal was found by Cheapflights users on 10/28. 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 11/261:15 pmMDW - FAI
2 stops14h 08mDelta
Tue 12/21:30 amFAI - MDW
2 stops13h 48mDelta
Deal found 10/28$540
This Delta deal was found by Cheapflights users on 10/27. 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 11/171:47 pmMDW - FAI
2 stops13h 36mDelta
Sun 11/231:30 amFAI - MDW
2 stops13h 48mDelta
Deal found 10/27$648
This Delta deal was found by Cheapflights users on 10/27. 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 11/201:15 pmMDW - FAI
2 stops14h 08mDelta
Fri 11/211:30 amFAI - MDW
2 stops13h 48mDelta
Deal found 10/27$667
This Delta deal was found by Cheapflights users on 10/27. 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 11/111:47 pmMDW - FAI
2 stops13h 36mDelta
Fri 11/141:30 amFAI - MDW
2 stops13h 48mDelta
Deal found 10/27$898

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Alaska 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 October 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Alaska that are best for you.

Fly from

Midway

Fly to

Alaska

Route

Depart

Return

Price

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 11/26

9:41 am-6:46 pm

1 stop12h 05m

Anchorage

Wed 12/3

9:45 pm-9:19 am

1 stop8h 34m

$358

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 4/1

1:00 pm-12:28 am

2 stops14h 28m

Anchorage

Wed 4/8

6:10 am-6:08 pm

1 stop8h 58m

$363

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 4/9

9:30 am-12:28 am

2 stops17h 58m

Anchorage

Mon 4/13

3:50 pm-12:30 pm

2 stops17h 40m

$370

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 11/21

1:47 pm-1:57 am

2 stops15h 10m

Anchorage

Mon 11/24

2:20 pm-9:01 am

2 stops15h 41m

$370

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 1/7

9:50 am-6:58 pm

1 stop12h 08m

Anchorage

Sun 1/11

6:10 am-6:32 pm

1 stop9h 22m

$378

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Sat 12/6

9:59 am-12:18 am

2 stops17h 19m

Fairbanks

Fri 12/12

1:30 am-6:18 pm

2 stops13h 48m

$392

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Wed 11/26

1:15 pm-12:23 am

2 stops14h 08m

Fairbanks

Tue 12/2

1:30 am-6:18 pm

2 stops13h 48m

$540

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Mon 11/17

1:47 pm-12:23 am

2 stops13h 36m

Fairbanks

Sun 11/23

1:30 am-6:18 pm

2 stops13h 48m

$648

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Thu 11/20

1:15 pm-12:23 am

2 stops14h 08m

Fairbanks

Fri 11/21

1:30 am-6:18 pm

2 stops13h 48m

$667

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Tue 11/11

1:47 pm-12:23 am

2 stops13h 36m

Fairbanks

Fri 11/14

1:30 am-6:18 pm

2 stops13h 48m

$898

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 33 results
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Best time to book a flight from Midway to Alaska

Have a flexible travel schedule? Discover the best time to fly to Alaska 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 Alaska

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

Find hourly flight availability from Midway to Alaska. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

It’s optimal to fly from Chicago Midway Airport to Alaska in the evening. By choosing this option you can save up to 54% on the cost of your flight, compared to a flight in the afternoon.

Related info for your journey

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

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

    Departing from Chicago Midway Airport to Alaska will take you 12h 05m. The distance from Chicago Midway Airport to Alaska is about 2852 mi.

  • What are the most popular routes from Chicago Midway Airport to Alaska?

    The most popular route from Chicago Midway Airport to Alaska is Chicago Midway - Anchorage. You may also consider Chicago Midway - Ketchikan or Chicago Midway - Fairbanks.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Alaska 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

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Alternative routes for Midway to Alaska

See prices for flight routes from nearby airports that may be better suited for you.
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