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Cheap flights from Anchorage to Chicago from $179

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Anchorage to Chicago departing on 5/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Anchorage to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:15 pm - 8:51 am
ANC
-
MDW
8h 36m
1 stop
Delta Logo
9:31 am - 6:46 pm
MDW
-
ANC
12h 15m
1 stop
$359Delta
Tue, Apr 14 - Mon, Apr 20
Delta Logo
9:55 pm - 8:42 am
ANC
-
MDW
7h 47m
1 stop
Delta Logo
1:22 pm - 1:35 am
MDW
-
ANC
15h 13m
2 stops
$364Delta
Thu, May 7 - Wed, May 13
Delta Logo
5:15 pm - 8:42 am
ANC
-
MDW
12h 27m
2 stops
Delta Logo
1:22 pm - 1:35 am
MDW
-
ANC
15h 13m
2 stops
$369Delta
Thu, May 7 - Wed, May 13
Delta Logo
9:15 pm - 1:25 pm
ANC
-
MDW
13h 10m
1 stop
Delta Logo
9:30 am - 6:51 pm
MDW
-
ANC
12h 21m
1 stop
$378Delta
Fri, Apr 3 - Sun, Apr 5
Delta Logo
9:15 pm - 1:25 pm
ANC
-
MDW
13h 10m
1 stop
Delta Logo
9:30 am - 8:35 pm
MDW
-
ANC
14h 05m
2 stops
$383Delta
Fri, Apr 3 - Sun, Apr 5
Delta Logo
9:15 pm - 12:46 pm
ANC
-
MDW
12h 31m
2 stops
Delta Logo
1:10 pm - 12:28 am
MDW
-
ANC
14h 18m
2 stops
$388Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
9:55 pm - 1:19 pm
ANC
-
MDW
12h 24m
1 stop
Delta Logo
1:59 pm - 12:33 am
MDW
-
ANC
13h 34m
1 stop
$391Delta
Wed, May 20 - Wed, May 27
Delta Logo
9:55 pm - 1:19 pm
ANC
-
MDW
12h 24m
1 stop
Delta Logo
1:59 pm - 1:35 am
MDW
-
ANC
14h 36m
2 stops
$396Delta
Wed, May 20 - Tue, May 26
Delta Logo
9:55 pm - 8:42 am
ANC
-
MDW
7h 47m
1 stop
Delta Logo
1:59 pm - 12:33 am
MDW
-
ANC
13h 34m
1 stop
$411Delta
Thu, May 7 - Wed, May 13
Delta Logo
9:55 pm - 1:07 pm
ANC
-
MDW
12h 12m
1 stop
Delta Logo
6:45 pm - 12:33 am
MDW
-
ANC
8h 48m
1 stop
$421Delta
Thu, Jul 30 - Sat, Aug 8

Delta flights from Anchorage to Chicago Midway Airport

Our best Delta deals on Anchorage to Chicago Midway Airport flight tickets
Delta
Apr 14
ANC9:15 pmAnchorage
8h 36m
1 stop
MDW8:51 amChicago Midway
Apr 20
MDW9:31 amChicago Midway
12h 15m
1 stop
ANC6:46 pmAnchorage
$359
Delta
May 7
ANC9:55 pmAnchorage
7h 47m
1 stop
MDW8:42 amChicago Midway
May 13
MDW1:59 pmChicago Midway
14h 36m
2 stops
ANC1:35 amAnchorage
$364
Delta
May 7
ANC5:15 pmAnchorage
12h 27m
2 stops
MDW8:42 amChicago Midway
May 13
MDW1:22 pmChicago Midway
15h 13m
2 stops
ANC1:35 amAnchorage
$369

Southwest flights from Anchorage to Chicago Midway Airport

Our best Southwest deals on Anchorage to Chicago Midway Airport flight tickets
Southwest
Jul 30
ANC12:55 amAnchorage
11h 20m
2 stops
MDW3:15 pmChicago Midway
Aug 8
MDW2:40 pmChicago Midway
12h 05m
2 stops
ANC11:45 pmAnchorage
$686
Southwest
Jul 29
ANC12:55 amAnchorage
10h 00m
1 stop
MDW1:55 pmChicago Midway
Aug 6
MDW1:50 pmChicago Midway
12h 55m
2 stops
ANC11:45 pmAnchorage
$728
Southwest
Jul 29
ANC12:55 amAnchorage
11h 20m
2 stops
MDW3:15 pmChicago Midway
Aug 6
MDW1:50 pmChicago Midway
12h 55m
2 stops
ANC11:45 pmAnchorage
$733

momondo Fare Finder

 
Customize your flight search to find flights from Anchorage to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 5, 2026.
Use the filters below to find and compare flights from Anchorage to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

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 5/7

9:55 pm-8:42 am

1 stop7h 47m

Chicago Midway

Wed 5/13

1:22 pm-1:35 am

2 stops15h 13m

$364

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

5:15 pm-8:42 am

2 stops12h 27m

Chicago Midway

Wed 5/13

1:22 pm-1:35 am

2 stops15h 13m

$369

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 4/3

9:15 pm-1:25 pm

1 stop13h 10m

Chicago Midway

Sun 4/5

9:30 am-6:51 pm

1 stop12h 21m

$378

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 4/3

9:15 pm-1:25 pm

1 stop13h 10m

Chicago Midway

Sun 4/5

9:30 am-8:35 pm

2 stops14h 05m

$383

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 3/2

9:15 pm-12:46 pm

2 stops12h 31m

Chicago Midway

Mon 3/9

1:10 pm-12:28 am

2 stops14h 18m

$388

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 5/20

9:55 pm-1:19 pm

1 stop12h 24m

Chicago Midway

Wed 5/27

1:59 pm-12:33 am

1 stop13h 34m

$391

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 5/20

9:55 pm-1:19 pm

1 stop12h 24m

Chicago Midway

Tue 5/26

1:59 pm-1:35 am

2 stops14h 36m

$396

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

9:55 pm-8:42 am

1 stop7h 47m

Chicago Midway

Wed 5/13

1:59 pm-12:33 am

1 stop13h 34m

$411

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 7/30

9:55 pm-1:07 pm

1 stop12h 12m

Chicago Midway

Sat 8/8

6:45 pm-12:33 am

1 stop8h 48m

$421

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Anchorage to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Anchorage to Chicago Midway?

Delta is the most popular carrier operating from Anchorage to Chicago Midway

When to book flights from Anchorage to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Anchorage to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Anchorage to Chicago Midway Airport (ANC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Anchorage to Chicago Midway Airport

Fastest flight time

7h 43m

Direct flights

None
The fastest flight from Anchorage to Chicago Midway Airport takes 7h 43m
There are no direct flights from Anchorage to Chicago Midway Airport. There are no popular flight routes from Anchorage to Chicago Midway Airport.
Search flight deals

  • How far is Anchorage to Chicago Midway by plane?

    The distance between Anchorage and Chicago Midway is about 2848.8 mi. A reasonable flight in good conditions will take 7h 43m.

  • When did momondo last update prices for flights from Anchorage Airport to Chicago Midway Airport?

    Prices for flights from Anchorage Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Anchorage Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Anchorage Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Anchorage to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Anchorage.

Can I find flights from Anchorage to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Anchorage which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Anchorage to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Anchorage to Chicago.

I’m not ready to book a flight from Anchorage to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Anchorage. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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