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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 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
sáb. 10/11
sáb. 10/18
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 septiembre 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 Alaska
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One-way flight from Chicago Midway to Alaska
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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 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 septiembre 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.
mar. 11/117:02 pmMDW - ANC
1 stop8h 54mDelta
mié. 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.
sáb. 11/87:10 pmMDW - ANC
1 stop8h 41mDelta
mié. 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.
mié. 10/221:08 pmMDW - ANC
2 stops12h 35mDelta
sáb. 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.
vie. 10/31:43 pmMDW - ANC
1 stop8h 10mDelta
lun. 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.
mié. 10/221:08 pmMDW - ANC
2 stops12h 35mDelta
dom. 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.
mié. 10/157:10 pmMDW - ANC
1 stop8h 41mDelta
sáb. 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.
jue. 10/29:20 amMDW - ANC
2 stops13h 59mDelta
lun. 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.
jue. 10/21:43 pmMDW - ANC
1 stop8h 10mDelta
mié. 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.
mié. 10/11:08 pmMDW - ANC
2 stops15h 29mDelta
mar. 10/712:30 amANC - MDW
2 stops14h 55mDelta
Deal found 9/10$382
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.
sáb. 10/189:20 amMDW - FAI
2 stops18h 25mDelta
lun. 10/271:45 amFAI - MDW
2 stops12h 58mDelta
Deal found 9/11$453
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.
mié. 11/51:08 pmMDW - FAI
2 stops14h 32mDelta
mar. 11/111:30 amFAI - MDW
2 stops12h 09mDelta
Deal found 9/10$456
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.
mar. 10/211:08 pmMDW - FAI
2 stops14h 32mDelta
vie. 10/241:45 amFAI - MDW
2 stops12h 58mDelta
Deal found 9/11$541

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 septiembre 11, 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

sáb. 10/4

11:00 am-6:56 pm

1 stop10h 56m

Anchorage

sáb. 10/11

6:05 am-5:43 pm

1 stop8h 38m

$338

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

sáb. 11/15

7:02 pm-12:56 am

1 stop8h 54m

Anchorage

mar. 12/9

6:05 am-6:18 pm

1 stop9h 13m

$338

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

lun. 10/27

7:10 pm-12:51 am

1 stop8h 41m

Anchorage

mié. 10/29

6:05 am-5:43 pm

1 stop8h 38m

$338

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

mié. 10/1

9:35 am-8:19 pm

2 stops13h 44m

Anchorage

sáb. 10/4

6:15 am-5:35 pm

1 stop8h 20m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

mié. 10/22

1:08 pm-10:43 pm

2 stops12h 35m

Anchorage

dom. 10/26

6:05 am-5:43 pm

1 stop8h 38m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

mié. 11/5

1:08 pm-10:43 pm

2 stops12h 35m

Anchorage

mié. 11/12

6:05 am-6:18 pm

1 stop9h 13m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

mié. 10/15

1:08 pm-10:43 pm

2 stops12h 35m

Anchorage

sáb. 10/25

6:05 am-5:43 pm

1 stop8h 38m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

mié. 10/22

1:08 pm-10:43 pm

2 stops12h 35m

Anchorage

sáb. 10/25

9:45 pm-8:55 am

1 stop8h 10m

$343

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

sáb. 11/8

6:00 am-6:31 pm

2 stops15h 31m

Anchorage

mié. 11/12

6:05 am-6:18 pm

1 stop9h 13m

$343

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

sáb. 10/18

9:20 am-12:45 am

2 stops18h 25m

Fairbanks

lun. 10/27

1:45 am-5:43 pm

2 stops12h 58m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 31 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 septiembre 11, 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.

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 10h 56m. 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.

  • 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 $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

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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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