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$178+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Find 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 October 28, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 12/129:45 pmANC - MDW
1 stop12h 25mDelta
Sun 12/2811:48 amMDW - ANC
1 stop10h 01mDelta
Deal found 10/27$358
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 12/56:05 amANC - MDW
1 stop9h 13mDelta
Mon 12/81:50 pmMDW - ANC
2 stops15h 03mDelta
Deal found 10/28$363
This Delta deal was found by Cheapflights users on 10/26. 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 11/186:05 amANC - MDW
1 stop9h 13mDelta
Sun 11/239:34 amMDW - ANC
2 stops16h 15mDelta
Deal found 10/26$425
This Delta deal was found by Cheapflights users on 10/26. 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 11/199:45 pmANC - MDW
1 stop8h 16mDelta
Mon 12/11:47 pmMDW - ANC
1 stop14h 09mDelta
Deal found 10/26$470
This Delta deal was found by Cheapflights users on 10/26. 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.
Sun 11/2312:30 amANC - MDW
2 stops14h 38mDelta
Tue 12/21:14 pmMDW - ANC
2 stops15h 40mDelta
Deal found 10/26$480
This Delta deal was found by Cheapflights users on 10/27. 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 11/139:45 pmANC - MDW
1 stop8h 16mDelta
Thu 11/206:00 amMDW - ANC
2 stops15h 46mDelta
Deal found 10/27$529

Cheap 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$358
(Delta)

One-way from

$178
(Delta)

Popular in

March

Cheapest in

November

Average price

$398
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. 16% potential increase in price ($101 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 28, 2025.
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

Mon 12/8

9:45 pm-1:10 pm

1 stop12h 25m

Chicago Midway

Thu 12/11

9:59 am-7:04 pm

1 stop12h 05m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 12/12

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

Sun 12/28

11:48 am-6:49 pm

1 stop10h 01m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 12/6

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

Mon 12/15

7:02 pm-12:57 am

1 stop8h 55m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 12/5

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

Mon 12/8

7:02 pm-12:57 am

1 stop8h 55m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 3/25

6:10 am-6:08 pm

1 stop8h 58m

Chicago Midway

Sun 3/29

6:45 pm-12:59 am

1 stop9h 14m

$390

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 11/24

9:45 pm-1:07 pm

1 stop12h 22m

$178

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 12/10

9:45 pm-9:19 am

1 stop8h 34m

$178

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 11/15

9:45 pm-9:01 am

1 stop8h 16m

$178

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 11/22

5:37 pm-8:54 am

2 stops12h 17m

$184

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 11/19

12:30 am-6:08 pm

2 stops14h 38m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Compare providers for flights from Anchorage to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Anchorage to Midway in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Anchorage-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Anchorage-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 12h 25m. Delta provides one of the quickest options available for as low as $358. 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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