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$168+ Cheap flights from Alaska to Midway (MDW)

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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — MDW
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find flight deals from Alaska to Midway

Cheapest flights from Alaska to Midway
Explore the most affordable flight options available from Alaska to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This Delta deal was found by Cheapflights users on 10/12. 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 11/116:05 amANC - MDW
1 stop9h 13mDelta
Tue 11/181:47 pmMDW - ANC
1 stop14h 09mDelta
Deal found 10/12$338
This Delta deal was found by Cheapflights users on 10/11. 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.
Mon 11/109:45 pmANC - MDW
1 stop12h 22mDelta
Fri 11/211:15 pmMDW - ANC
2 stops15h 42mDelta
Deal found 10/11$375
This Delta deal was found by Cheapflights users on 10/11. 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.
Wed 11/196:05 amANC - MDW
1 stop9h 13mDelta
Fri 11/217:02 pmMDW - ANC
1 stop8h 54mDelta
Deal found 10/11$378
This Delta deal was found by Cheapflights users on 10/12. 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 11/269:45 pmANC - MDW
1 stop8h 16mDelta
Wed 12/31:14 pmMDW - ANC
2 stops15h 40mDelta
Deal found 10/12$383

Cheap flight deals from Alaska to Midway

Keep the following information in mind while searching for Alaska to Midway flight deals. Data was last updated October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$338
(Delta)

One-way from

$168
(Delta)

Popular in

March

Cheapest in

October

Average price

$318
Provider with most accurate pricing for Anchorage-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
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From Alaska to Chicago Midway
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One-way flight from Alaska to Chicago Midway
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Highest demand for flights based on searches. 17% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
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 October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Alaska to Midway 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 14, 2025.
Use the filters below to find and compare flights from Alaska to Chicago Midway Airport that are best for you.

Fly from

Alaska

Fly to

Midway

Route

Depart

Return

Price

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 11/11

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

Tue 11/18

1:47 pm-12:56 am

1 stop14h 09m

$338

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/7

6:10 am-6:08 pm

1 stop8h 58m

Chicago Midway

Wed 4/8

9:20 am-7:10 pm

1 stop12h 50m

$338

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 1/10

3:50 pm-8:50 am

2 stops14h 00m

Chicago Midway

Sat 1/17

2:00 pm-12:59 am

1 stop13h 59m

$343

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 11/19

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

Fri 11/21

1:15 pm-1:57 am

2 stops15h 42m

$375

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 3/24

12:40 am-6:08 pm

2 stops14h 28m

Chicago Midway

Sun 3/29

6:45 pm-12:59 am

1 stop9h 14m

$383

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 11/26

9:45 pm-9:01 am

1 stop8h 16m

Chicago Midway

Wed 12/3

1:14 pm-1:54 am

2 stops15h 40m

$383

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Fri 2/27

1:30 am-9:46 pm

2 stops17h 16m

Chicago Midway

Mon 3/2

9:20 am-12:13 am

2 stops17h 53m

$844

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 11/14

9:45 pm-1:07 pm

1 stop12h 22m

$168

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 11/7

9:45 pm-1:08 pm

1 stop12h 23m

$168

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 10/26

9:45 pm-8:55 am

1 stop8h 10m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 12 results
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Best time to book a flight from Alaska to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Alaska 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 Alaska to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Alaska to Midway. 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 Alaska to Chicago Midway Airport?

    There are many flights that can get you from Alaska to Chicago Midway Airport in 9h 13m. Fly via Delta to get the fastest option. Alaska and Chicago Midway Airport are separated by a distance of 2852 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Alaska to Midway 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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