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$260+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$402
(Delta)

One-way from

$260
(Delta)

Popular in

December

Cheapest in

April

Average price

$399
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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Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/249:16 amMDW - ANC
1 stop14h 29mDelta
Sat 5/318:15 pmANC - MDW
1 stop10h 25mDelta
Deal found 4/29$396
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 5/291:55 pmMDW - FAI
2 stops13h 33mDelta
Mon 6/910:05 pmFAI - MDW
1 stop7h 39mDelta
Deal found 4/29$546
This Delta deal was found by Cheapflights users on 4/29. 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 6/119:24 amMDW - JNU
2 stops11h 43mDelta
Wed 6/187:05 amJNU - MDW
2 stops11h 40mDelta
Deal found 4/29$668

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 April 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

Sat 5/24

9:16 am-8:45 pm

1 stop14h 29m

Anchorage

Sat 5/31

5:15 pm-8:40 am

2 stops12h 25m

$402

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Thu 5/29

1:55 pm-12:28 am

2 stops13h 33m

Fairbanks

Mon 6/9

10:05 pm-8:44 am

1 stop7h 39m

$546

ChicagoJuneau

MDW - JNU

MDWJNU

Chicago Midway

Thu 6/12

9:24 am-6:07 pm

2 stops11h 43m

Juneau Intl

Thu 6/19

7:05 am-9:45 pm

2 stops11h 40m

$999

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 5/30

7:25 pm-12:50 am

1 stop8h 25m

$260

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Thu 6/12

1:47 pm-8:55 pm

1 stop10h 08m

$271

ChicagoJuneau

MDW - JNU

MDWJNU

Chicago Midway

Tue 6/17

9:24 am-6:07 pm

2 stops11h 43m

$296

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 5/30

8:04 pm-12:18 pm

3 stops43h 14m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April 29, 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.

Rainfall in Alaska by month

Plan your trip to Alaska by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Alaska ranges from 0.5 - 3.3 inches per month. August is typically the wettest month, when rainfall can reach 3.3 in. April is typically the driest time to visit Alaska when rainfall is around 0.5 in.

Temperature in Alaska by month

Plan your trip to Alaska by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Alaska, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 59.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 17.6 F).

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 April 29, 2025.
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 - Fairbanks or Chicago Midway - Juneau Intl.

  • 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 $651). 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.

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Alternative routes for Midway to Alaska

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