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Midway

$179+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — MDW
Feb 17 — Feb 241
Tue 2/17
Tue 2/24
1 adult, Economy
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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 January 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$359
(Delta)

One-way from

$179
(Delta)

Popular in

March

Cheapest in

October

Average price

$524
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. 25% potential increase in price ($170 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 18, 2026.

This Delta deal was found by Cheapflights users on 1/18. 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 5/79:55 pm
ANC
-
MDW
1 stop7h 43m
Delta
Wed 5/132:00 pm
MDW
-
ANC
1 stop13h 33m
Delta
Deal found 1/18$359
This Delta deal was found by Cheapflights users on 1/17. 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 2/149:15 pm
ANC
-
MDW
1 stop10h 48m
Delta
Wed 3/187:20 pm
MDW
-
ANC
1 stop26h 31m
Delta
Deal found 1/17$360
This Delta deal was found by Cheapflights users on 1/16. 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 2/141:15 pm
ANC
-
MDW
2 stops16h 39m
Delta
Mon 3/231:10 pm
MDW
-
ANC
2 stops14h 19m
Delta
Deal found 1/16$369
This Delta deal was found by Cheapflights users on 1/17. 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 2/149:15 pm
ANC
-
MDW
1 stop10h 48m
Delta
Thu 3/199:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Deal found 1/17$378
This Delta deal was found by Cheapflights users on 1/17. 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 2/119:15 pm
ANC
-
MDW
1 stop12h 50m
Delta
Sun 2/159:34 am
MDW
-
ANC
2 stops16h 12m
Delta
Deal found 1/17$433
This Delta deal was found by Cheapflights users on 1/18. 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 3/129:15 pm
ANC
-
MDW
1 stop13h 10m
Delta
Thu 3/199:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Deal found 1/18$451
This Delta deal was found by Cheapflights users on 1/16. 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 3/11:27 am
FAI
-
MDW
2 stops14h 13m
Delta
Mon 3/91:10 pm
MDW
-
FAI
2 stops14h 01m
Delta
Deal found 1/16$453
This Delta deal was found by Cheapflights users on 1/17. 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 2/159:15 pm
ANC
-
MDW
1 stop8h 51m
Delta
Thu 3/192:05 pm
MDW
-
ANC
2 stops13h 24m
Delta
Deal found 1/17$456
This Delta deal was found by Cheapflights users on 1/18. 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 2/11:30 am
FAI
-
MDW
2 stops14h 06m
Delta
Fri 2/69:53 am
MDW
-
FAI
2 stops17h 29m
Delta
Deal found 1/18$613
This Delta deal was found by Cheapflights users on 1/18. 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 3/251:30 am
FAI
-
MDW
2 stops13h 24m
Delta
Mon 3/302:05 pm
MDW
-
FAI
2 stops13h 07m
Delta
Deal found 1/18$744
This Delta deal was found by Cheapflights users on 1/17. 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 2/91:30 am
FAI
-
MDW
2 stops14h 06m
Delta
Sat 2/149:34 am
MDW
-
FAI
2 stops17h 48m
Delta
Deal found 1/17$889
This Delta deal was found by Cheapflights users on 1/16. 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 1/301:30 am
FAI
-
MDW
2 stops17h 52m
Delta
Wed 2/49:32 am
MDW
-
FAI
2 stops17h 50m
Delta
Deal found 1/16$978

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 January 18, 2026.
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

Sat 2/14

9:15 pm-11:03 am

1 stop10h 48m

Chicago Midway

Mon 3/23

9:30 am-6:51 pm

1 stop12h 21m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

9:55 pm-8:38 am

1 stop7h 43m

Chicago Midway

Wed 5/13

2:00 pm-12:33 am

1 stop13h 33m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 2/14

9:15 pm-11:03 am

1 stop10h 48m

Chicago Midway

Wed 3/18

7:20 pm-6:51 pm

1 stop26h 31m

$360

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 2/15

9:15 pm-9:06 am

1 stop8h 51m

Chicago Midway

Wed 3/18

7:20 pm-6:51 pm

1 stop26h 31m

$360

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 2/15

9:15 pm-9:06 am

1 stop8h 51m

Chicago Midway

Thu 3/19

9:30 am-6:51 pm

1 stop12h 21m

$378

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 2/14

9:15 pm-11:03 am

1 stop10h 48m

Chicago Midway

Thu 3/19

9:30 am-6:51 pm

1 stop12h 21m

$378

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Sun 3/1

1:27 am-6:40 pm

2 stops14h 13m

Chicago Midway

Mon 3/9

1:10 pm-12:11 am

2 stops14h 01m

$453

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Sun 2/1

1:30 am-6:36 pm

2 stops14h 06m

Chicago Midway

Fri 2/6

9:53 am-12:22 am

2 stops17h 29m

$613

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Wed 3/25

1:30 am-5:54 pm

2 stops13h 24m

Chicago Midway

Mon 3/30

2:05 pm-12:12 am

2 stops13h 07m

$744

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Mon 2/9

1:30 am-6:36 pm

2 stops14h 06m

Chicago Midway

Sat 2/14

9:34 am-12:22 am

2 stops17h 48m

$889

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 27 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 10h 48m. 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Alaska to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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John F Kennedy Intl to Midway flights
Los Angeles to Midway flights
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Seattle to O'Hare Intl flights
Dulles Intl to Midway flights
Charlotte to O'Hare Intl flights
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Minneapolis to O'Hare Intl flights
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Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
Love Field to O'Hare Intl flights
Hobby to O'Hare Intl flights
Denver to Midway flights
San Diego to O'Hare Intl flights
San Francisco to Midway flights
Orlando to Midway flights
Hobby to Midway flights
Fort Lauderdale to O'Hare Intl flights
Philadelphia to Midway flights
Detroit to O'Hare Intl flights
Hartford to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Tampa to O'Hare Intl flights
Reagan-National to Midway flights
Love Field to Midway flights
Nashville to O'Hare Intl flights
Miami to O'Hare Intl flights
Boston to Midway flights

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