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$180+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/26. 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 3/109:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Thu 3/199:15 pm
ANC
-
MDW
1 stop18h 25m
Delta
Deal found 1/26$359
This Delta deal was found by Cheapflights users on 1/27. 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 2/197:20 pm
MDW
-
ANC
1 stop26h 37m
Delta
Mon 2/239:15 pm
ANC
-
MDW
1 stop18h 25m
Delta
Deal found 1/27$360
This Delta deal was found by Cheapflights users on 1/28. 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 7/211:00 pm
MDW
-
ANC
2 stops27h 41m
Delta
Fri 7/2412:49 pm
ANC
-
MDW
1 stop16h 49m
Delta
Deal found 1/28$365
This Delta deal was found by Cheapflights users on 1/27. 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 4/169:31 am
MDW
-
ANC
1 stop12h 15m
Delta
Mon 4/203:45 pm
ANC
-
MDW
2 stops14h 02m
Delta
Deal found 1/27$366
This Delta deal was found by Cheapflights users on 1/27. 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 7/31:00 pm
MDW
-
ANC
2 stops15h 35m
Delta
Fri 7/105:15 pm
ANC
-
MDW
2 stops12h 23m
Delta
Deal found 1/27$371
This Delta deal was found by Cheapflights users on 1/28. 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 7/211:00 pm
MDW
-
ANC
2 stops27h 41m
Delta
Mon 7/275:15 pm
ANC
-
MDW
2 stops16h 15m
Delta
Deal found 1/28$372
This Delta deal was found by Cheapflights users on 1/26. 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 3/119:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Sat 3/219:15 pm
ANC
-
MDW
1 stop13h 10m
Delta
Deal found 1/26$378
This Delta deal was found by Cheapflights users on 1/28. 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 3/192:05 pm
MDW
-
ANC
2 stops13h 24m
Delta
Mon 3/239:15 pm
ANC
-
MDW
1 stop13h 10m
Delta
Deal found 1/28$383
This Delta deal was found by Cheapflights users on 1/26. 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 3/119:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Sun 3/223:40 pm
ANC
-
MDW
2 stops18h 45m
Delta
Deal found 1/26$385
This Delta deal was found by Cheapflights users on 1/27. 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 3/91:10 pm
MDW
-
ANC
2 stops14h 18m
Delta
Fri 3/131:20 pm
ANC
-
MDW
2 stops16h 33m
Delta
Deal found 1/27$390
This Delta deal was found by Cheapflights users on 1/27. 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 7/39:20 am
MDW
-
ANC
1 stop18h 13m
Delta
Thu 7/910:00 pm
ANC
-
MDW
1 stop17h 31m
Delta
Deal found 1/27$391
This Delta deal was found by Cheapflights users on 1/27. 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 2/2111:45 am
MDW
-
FAI
2 stops15h 37m
Delta
Tue 2/241:27 am
FAI
-
MDW
2 stops13h 10m
Delta
Deal found 1/27$484

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$359
(Delta)

One-way from

$180
(Delta)

Popular in

June

Cheapest in

October

Average price

$459
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 ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Tue 3/10

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Thu 3/19

9:15 pm-6:40 pm

1 stop18h 25m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 7/7

9:20 am-12:33 am

1 stop18h 13m

Anchorage

Fri 7/17

12:49 pm-8:38 am

1 stop16h 49m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 5/27

2:00 pm-12:33 am

1 stop13h 33m

Anchorage

Mon 6/8

10:00 pm-6:31 pm

1 stop17h 31m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 7/6

6:45 pm-12:33 am

1 stop8h 48m

Anchorage

Tue 7/14

10:00 pm-6:31 pm

1 stop17h 31m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 5/27

2:00 pm-12:33 am

1 stop13h 33m

Anchorage

Wed 6/10

9:55 pm-8:38 am

1 stop7h 43m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 3/10

9:30 am-6:51 pm

1 stop12h 21m

Anchorage

Fri 3/20

9:15 pm-6:40 pm

1 stop18h 25m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 5/29

9:20 am-12:33 am

1 stop18h 13m

Anchorage

Tue 6/9

6:10 am-6:05 pm

1 stop8h 55m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 2/20

9:50 am-6:57 pm

1 stop12h 07m

Anchorage

Mon 2/23

9:15 pm-6:40 pm

1 stop18h 25m

$359

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 4/2

9:30 am-8:35 pm

2 stops14h 05m

Anchorage

Sun 4/5

9:15 pm-8:50 am

1 stop8h 35m

$364

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 3/20

2:05 pm-12:29 am

2 stops13h 24m

Anchorage

Mon 3/23

9:15 pm-1:25 pm

1 stop13h 10m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 34 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
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 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 21m. 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 - Fairbanks 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

Browse thousands of different options on Cheapflights for your next trip

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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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