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$170+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$338
(Delta)

One-way from

$170
(Delta)

Popular in

December

Cheapest in

October

Average price

$552
From Chicago Midway to Alaska
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One-way flight from Chicago Midway to Alaska
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Highest demand for flights based on searches. 1% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 10/157:10 pmMDW - ANC
1 stop8h 41mDelta
Fri 10/176:05 amANC - MDW
1 stop8h 38mDelta
Deal found 7/29$338
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 8/271:08 pmMDW - FAI
2 stops14h 42mDelta
Sun 8/3110:07 pmFAI - MDW
1 stop7h 43mDelta
Deal found 7/29$482
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 8/269:30 amMDW - JNU
2 stops11h 41mDelta
Tue 9/27:05 amJNU - MDW
2 stops11h 21mDelta
Deal found 7/29$653

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 July 30, 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 10/15

7:10 pm-12:51 am

1 stop8h 41m

Anchorage

Fri 10/17

6:05 am-5:43 pm

1 stop8h 38m

$338

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Wed 8/27

1:08 pm-12:50 am

2 stops14h 42m

Fairbanks

Sun 8/31

10:07 pm-8:50 am

1 stop7h 43m

$482

ChicagoJuneau

MDW - JNU

MDWJNU

Chicago Midway

Tue 8/26

9:30 am-6:11 pm

2 stops11h 41m

Juneau Intl

Tue 9/2

7:05 am-9:26 pm

2 stops11h 21m

$653

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 8/23

7:17 pm-1:35 am

1 stop9h 18m

$170

ChicagoJuneau

MDW - JNU

MDWJNU

Chicago Midway

Sat 8/23

9:31 am-6:11 pm

2 stops11h 40m

$317

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Sat 8/9

1:09 pm-11:25 pm

2 stops13h 16m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Alaska as you normally would.

Reviews of airlines servicing Alaska

Get insights into the airlines that provide service to Alaska. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Alaska. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Alaska, such as Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 - Juneau Intl 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Alaska (average of $456). Flying from Chicago Midway Airport to Alaska in July is currently the most expensive (average of $645). 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

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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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