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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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — MDW
janv. 11 — janv. 181
dim. 1/11
dim. 1/18
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 décembre 12, 2025.

This Delta deal was found by Cheapflights users on 12/9. 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.
lun. 12/156:05 amANC - MDW
1 stop9h 13mDelta
ven. 12/199:59 amMDW - ANC
1 stop12h 05mDelta
Deal found 12/9$812
This Delta deal was found by Cheapflights users on 12/11. 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.
ven. 12/126:05 amANC - MDW
1 stop9h 13mDelta
dim. 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/11$887
This Delta deal was found by Cheapflights users on 12/11. 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.
mar. 12/238:15 pmANC - MDW
1 stop15h 29mDelta
dim. 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/11$936
This Delta deal was found by Cheapflights users on 12/11. 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.
mer. 12/241:44 pmANC - MDW
2 stops16h 05mDelta
dim. 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/11$941
This Delta deal was found by Cheapflights users on 12/11. 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.
ven. 12/263:40 pmANC - MDW
2 stops14h 09mDelta
dim. 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/11$965

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 décembre 12, 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

October

Average price

$408
Provider with most accurate pricing for Anchorage-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Anchorage-Chicago Midway flights.
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From Anchorage to Chicago Midway
Search Deals
One-way flight from Anchorage to Chicago Midway
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($158 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 décembre 12, 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

mar. 1/20

9:15 pm-1:09 pm

1 stop12h 54m

Chicago Midway

mar. 1/27

9:50 am-6:56 pm

1 stop12h 06m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

ven. 1/9

9:15 pm-11:05 am

1 stop10h 50m

Chicago Midway

mar. 1/13

7:16 pm-12:48 am

1 stop8h 32m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

sam. 1/10

8:22 pm-10:27 am

1 stop11h 05m

Chicago Midway

sam. 1/17

11:45 am-12:09 am

2 stops15h 24m

$363

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

jeu. 1/15

6:10 am-6:32 pm

1 stop9h 22m

Chicago Midway

lun. 1/19

9:50 am-6:56 pm

1 stop12h 06m

$390

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

lun. 1/12

9:15 pm-9:08 am

1 stop8h 53m

Chicago Midway

lun. 1/19

9:50 am-12:09 am

2 stops17h 19m

$433

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

sam. 5/23

10:00 pm-12:30 pm

1 stop11h 30m

$178

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

ven. 6/5

12:30 am-6:05 pm

2 stops14h 35m

$189

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

mar. 12/30

8:15 pm-2:44 pm

1 stop15h 29m

$344

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

lun. 12/22

9:15 pm-4:20 pm

2 stops16h 05m

$499

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

ven. 6/5

2:28 am-8:42 am

3 stops27h 14m

$538

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 11 results
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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 December.
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 54m. 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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