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$179+ Cheap flights from Anchorage (ANC) 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — MDW
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Anchorage to Midway

Cheapest flights from Anchorage to Midway
Explore the most affordable flight options available from Anchorage to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This Delta deal was found by Cheapflights users on 1/24. 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 3/199:15 pm
ANC
-
MDW
1 stop8h 35m
Delta
Mon 3/239:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Deal found 1/24$359
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.
Fri 2/203:21 pm
ANC
-
MDW
2 stops18h 25m
Delta
Sun 2/229:34 am
MDW
-
ANC
2 stops17h 35m
Delta
Deal found 1/26$369
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.
Thu 5/79:55 pm
ANC
-
MDW
1 stop7h 43m
Delta
Wed 5/132:00 pm
MDW
-
ANC
1 stop13h 33m
Delta
Deal found 1/26$378
This Delta deal was found by Cheapflights users on 1/24. 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 5/216:10 am
ANC
-
MDW
1 stop8h 55m
Delta
Mon 5/251:00 pm
MDW
-
ANC
2 stops15h 35m
Delta
Deal found 1/24$396
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.
Fri 5/89:55 pm
ANC
-
MDW
1 stop7h 43m
Delta
Sun 5/109:20 am
MDW
-
ANC
1 stop12h 28m
Delta
Deal found 1/26$411
This Delta deal was found by Cheapflights users on 1/25. 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 3/243:40 pm
ANC
-
MDW
2 stops14h 13m
Delta
Sat 3/289:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Deal found 1/25$414
This Delta deal was found by Cheapflights users on 1/25. 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 4/139:15 pm
ANC
-
MDW
2 stops12h 28m
Delta
Sun 4/196:00 am
MDW
-
ANC
2 stops15h 46m
Delta
Deal found 1/25$419
This Delta deal was found by Cheapflights users on 1/25. 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 3/183:40 pm
ANC
-
MDW
2 stops14h 13m
Delta
Wed 3/259:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Deal found 1/25$456
This Delta deal was found by Cheapflights users on 1/23. 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 4/83:40 pm
ANC
-
MDW
2 stops14h 13m
Delta
Mon 4/132:12 pm
MDW
-
ANC
2 stops13h 25m
Delta
Deal found 1/23$511

Find flight deals from Anchorage to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Anchorage (ANC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

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 Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Anchorage-Chicago Midway flights.
Search Deals
From Anchorage to Chicago Midway
Search Deals
One-way flight from Anchorage to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 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 Anchorage 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 26, 2026.
Use the filters below to find and compare flights from Anchorage to Chicago Midway Airport that are best for you.

Fly from

Anchorage

Fly to

Midway

Route

Depart

Return

Price

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 3/19

9:15 pm-8:50 am

1 stop8h 35m

Chicago Midway

Mon 3/23

9:30 am-6:51 pm

1 stop12h 21m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 3/24

9:15 pm-1:25 pm

1 stop13h 10m

Chicago Midway

Sat 3/28

9:30 am-6:51 pm

1 stop12h 21m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 4/8

9:15 pm-8:50 am

1 stop8h 35m

Chicago Midway

Mon 4/13

9:26 am-6:46 pm

1 stop12h 20m

$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

Mon 4/13

9:15 pm-1:32 pm

1 stop13h 17m

Chicago Midway

Mon 4/20

9:31 am-6:46 pm

1 stop12h 15m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/14

9:15 pm-8:51 am

1 stop8h 36m

Chicago Midway

Mon 4/20

9:31 am-6:46 pm

1 stop12h 15m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/21

6:10 am-6:05 pm

1 stop8h 55m

Chicago Midway

Mon 5/25

1:00 pm-8:58 pm

1 stop10h 58m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 5/8

5:15 pm-8:38 am

2 stops12h 23m

Chicago Midway

Sun 5/10

1:00 pm-1:35 am

2 stops15h 35m

$369

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 5/23

10:00 pm-12:30 pm

1 stop11h 30m

$179

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 2/24

9:15 pm-9:06 am

1 stop8h 51m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 14 results
1
2
  • Most accurate provider: When it comes to deals on Anchorage-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Anchorage-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Anchorage-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Anchorage-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Anchorage-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Anchorage to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Anchorage 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.

Related info for your journey

Find useful and relevant information for your journey from Anchorage to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Anchorage to Chicago Midway?

    Anchorage (ANC) is the airport you will fly out of if you book a flight from Anchorage to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Anchorage; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Anchorage airport to Chicago Midway. It is only a 4.4 mi journey to Anchorage (ANC) from Anchorage’s city center.

  • How long is the flight from Anchorage to Chicago Midway Airport?

    A quick flight from Anchorage to Chicago Midway Airport can take about 8h 35m. Delta provides one of the quickest options available for as low as $359. There are 2852 mi between Anchorage and Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Anchorage 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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