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$178+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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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 November 26, 2025.

This Delta deal was found by Cheapflights users on 11/25. 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 12/166:05 amANC - MDW
1 stop9h 13mDelta
Tue 1/61:49 pmMDW - ANC
1 stop13h 59mDelta
Deal found 11/25$358
This Delta deal was found by Cheapflights users on 11/24. 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.
Fri 12/269:15 pmANC - MDW
1 stop10h 51mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 11/24$460
This Delta deal was found by Cheapflights users on 11/24. 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.
Wed 12/241:44 pmANC - MDW
2 stops16h 05mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 11/24$497
This Delta deal was found by Cheapflights users on 11/24. 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.
Tue 12/238:15 pmANC - MDW
1 stop15h 29mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 11/24$510
This Delta deal was found by Cheapflights users on 11/23. 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.
Mon 12/81:30 amFAI - MDW
2 stops13h 48mDelta
Sat 12/131:50 pmMDW - FAI
2 stops13h 28mDelta
Deal found 11/23$612
This Delta deal was found by Cheapflights users on 11/24. 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.
Mon 12/223:40 pmANC - MDW
2 stops14h 09mDelta
Wed 12/316:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 11/24$621
This Delta deal was found by Cheapflights users on 11/24. 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.
Fri 12/129:45 pmANC - MDW
1 stop8h 34mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 11/24$626
This Delta deal was found by Cheapflights users on 11/26. 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.
Mon 12/223:40 pmANC - MDW
2 stops14h 09mDelta
Fri 12/2611:48 amMDW - ANC
2 stops15h 11mDelta
Deal found 11/26$636
This Delta deal was found by Cheapflights users on 11/24. 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.
Fri 12/51:30 amFAI - MDW
2 stops13h 48mDelta
Tue 12/91:14 pmMDW - FAI
2 stops14h 04mDelta
Deal found 11/24$752
This Delta deal was found by Cheapflights users on 11/26. 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.
Sat 12/201:50 amFAI - MDW
2 stops12h 29mDelta
Mon 12/2911:48 amMDW - FAI
2 stops15h 57mDelta
Deal found 11/26$2,448

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 November 26, 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

$398
Provider with most accurate pricing for Anchorage-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
Search Deals
From Alaska to Chicago Midway
Search Deals
One-way flight from Alaska to Chicago Midway
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($118 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 November 26, 2025.
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

Tue 12/16

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

Tue 1/6

1:49 pm-12:48 am

1 stop13h 59m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 2/24

9:15 pm-9:06 am

1 stop8h 51m

Chicago Midway

Sat 2/28

11:45 am-6:57 pm

1 stop10h 12m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 2/10

9:15 pm-9:08 am

1 stop8h 53m

Chicago Midway

Sat 2/14

11:45 am-6:57 pm

1 stop10h 12m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 2/27

9:15 pm-11:03 am

1 stop10h 48m

Chicago Midway

Sun 3/1

9:50 am-6:57 pm

1 stop12h 07m

$358

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Mon 12/8

1:30 am-6:18 pm

2 stops13h 48m

Chicago Midway

Sat 12/13

1:50 pm-12:18 am

2 stops13h 28m

$612

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Sat 12/6

1:30 am-6:18 pm

2 stops13h 48m

Chicago Midway

Tue 12/9

1:14 pm-12:18 am

2 stops14h 04m

$752

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Sat 12/20

1:50 am-5:19 pm

2 stops12h 29m

Chicago Midway

Mon 12/29

11:48 am-12:45 am

2 stops15h 57m

$2,448

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 3/25

9:15 pm-1:23 pm

1 stop13h 08m

$178

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 5/23

9:55 pm-1:07 pm

1 stop12h 12m

$178

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 12/31

9:15 pm-11:06 am

1 stop10h 51m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 11 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 9h 13m. 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
Hammond
Porter
Benton Harbor
Merrillville

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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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