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$346+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/2411:48 amMDW - ANC
1 stop10h 01mDelta
Wed 12/318:15 pmANC - MDW
1 stop9h 50mDelta
Deal found 12/9$524
This Delta deal was found by Cheapflights users on 12/10. 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.
Tue 12/306:00 amMDW - ANC
1 stop15h 57mDelta
Fri 1/93:00 pmANC - MDW
2 stops14h 52mDelta
Deal found 12/10$530
This Delta deal was found by Cheapflights users on 12/10. 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 12/266:00 amMDW - ANC
1 stop15h 57mDelta
Tue 1/69:15 pmANC - MDW
1 stop12h 54mDelta
Deal found 12/10$600
This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/316:00 amMDW - ANC
1 stop15h 57mDelta
Sun 1/49:15 pmANC - MDW
1 stop12h 54mDelta
Deal found 12/9$687
This Delta deal was found by Cheapflights users on 12/10. 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 12/266:00 amMDW - ANC
1 stop15h 57mDelta
Sun 1/49:15 pmANC - MDW
1 stop12h 54mDelta
Deal found 12/10$702
This Delta deal was found by Cheapflights users on 12/9. 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 12/181:50 pmMDW - ANC
1 stop14h 07mDelta
Mon 12/229:15 pmANC - MDW
1 stop10h 51mDelta
Deal found 12/9$740
This Delta deal was found by Cheapflights users on 12/10. 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.
Sun 12/289:29 amMDW - FAI
2 stops18h 16mDelta
Thu 1/11:50 amFAI - MDW
2 stops12h 29mDelta
Deal found 12/10$1,634
This Delta deal was found by Cheapflights users on 12/10. 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.
Mon 12/299:29 amMDW - FAI
2 stops18h 16mDelta
Sat 1/31:40 amFAI - MDW
2 stops12h 39mDelta
Deal found 12/10$2,039
This Delta deal was found by Cheapflights users on 12/11. 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.
Tue 12/161:14 pmMDW - FAI
2 stops14h 04mDelta
Sun 12/211:50 amFAI - MDW
2 stops17h 32mDelta
Deal found 12/11$2,376
This Delta deal was found by Cheapflights users on 12/10. 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 12/2611:48 amMDW - FAI
2 stops15h 57mDelta
Mon 12/291:50 amFAI - MDW
2 stops12h 29mDelta
Deal found 12/10$2,452

Find flight deals from Midway to Alaska

Keep the following information in mind while searching for Midway to Alaska flight deals. Data was last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$358
(Delta)

One-way from

$346
(Delta)

Popular in

June

Cheapest in

October

Average price

$461
Provider with most accurate pricing for Chicago (CHI)-Anchorage flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Anchorage flights.
Search Deals
From Chicago Midway to Alaska
Search Deals
One-way flight from Chicago Midway to Alaska
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 12, 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 2/11

9:53 am-6:56 pm

1 stop12h 03m

Anchorage

Tue 2/17

9:15 pm-9:06 am

1 stop8h 51m

$358

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 1/8

7:16 pm-12:48 am

1 stop8h 32m

Anchorage

Wed 1/14

9:15 pm-9:08 am

1 stop8h 53m

$358

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 1/5

1:49 pm-12:48 am

1 stop13h 59m

Anchorage

Sat 1/10

9:15 pm-9:08 am

1 stop8h 53m

$358

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 1/5

9:50 am-12:48 am

1 stop17h 58m

Anchorage

Fri 1/9

9:15 pm-11:05 am

1 stop10h 50m

$358

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 1/17

11:45 am-12:09 am

2 stops15h 24m

Anchorage

Sun 1/25

9:15 pm-9:08 am

1 stop8h 53m

$363

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 2/11

9:53 am-6:56 pm

1 stop12h 03m

Anchorage

Mon 2/16

3:16 pm-8:53 am

2 stops14h 37m

$364

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 2/13

9:50 am-6:57 pm

1 stop12h 07m

Anchorage

Mon 2/16

9:15 pm-1:07 pm

1 stop12h 52m

$390

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 1/7

1:49 pm-12:48 am

1 stop13h 59m

Anchorage

Wed 1/14

6:10 am-6:32 pm

1 stop9h 22m

$390

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Wed 2/4

9:53 am-12:22 am

2 stops17h 29m

Fairbanks

Mon 2/9

1:30 am-6:36 pm

2 stops14h 06m

$394

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Thu 1/15

9:50 am-12:25 am

2 stops17h 35m

Fairbanks

Sat 1/17

1:30 am-10:07 pm

2 stops17h 37m

$603

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 21 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 December 12, 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 03m. 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 - Juneau Intl or Chicago Midway - Ketchikan.

  • 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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