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Cheap flights from Anchorage to Chicago from $196

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 7/1. 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
6:00 am - 6:01 pm
ANC
-
MDW
9h 01m
1 stop
Delta Logo
9:24 am - 8:56 pm
MDW
-
ANC
14h 32m
1 stop
$393Delta
Tue, Aug 25 - Sat, Aug 29
Delta Logo
10:37 pm - 12:39 pm
ANC
-
MDW
11h 02m
1 stop
Delta Logo
1:27 pm - 11:58 pm
MDW
-
ANC
13h 31m
2 stops
$398Delta
Tue, Aug 25 - Sat, Aug 29
Delta Logo
2:20 pm - 8:49 am
ANC
-
MDW
15h 29m
2 stops
Delta Logo
12:30 pm - 10:36 pm
MDW
-
ANC
13h 06m
2 stops
$403Delta
Thu, Nov 12 - Mon, Nov 16
Delta Logo
9:55 pm - 8:49 am
ANC
-
MDW
7h 54m
1 stop
Delta Logo
12:30 pm - 9:03 pm
MDW
-
ANC
11h 33m
1 stop
$406Delta
Mon, Nov 2 - Sat, Nov 7
Delta Logo
9:55 pm - 8:49 am
ANC
-
MDW
7h 54m
1 stop
Delta Logo
9:30 am - 9:03 pm
MDW
-
ANC
14h 33m
2 stops
$411Delta
Mon, Nov 2 - Sat, Nov 7
Delta Logo
10:30 pm - 6:31 pm
ANC
-
MDW
17h 01m
1 stop
Delta Logo
6:58 pm - 1:15 pm
MDW
-
ANC
21h 17m
2 stops
$443Delta
Sun, Jun 21 - Mon, Jun 29
Delta Logo
2:10 pm - 8:37 am
ANC
-
MDW
15h 27m
2 stops
Delta Logo
9:17 am - 11:20 pm
MDW
-
ANC
17h 03m
2 stops
$444Delta
Fri, Jun 26 - Fri, Jul 3
Delta Logo
6:00 am - 6:18 pm
ANC
-
MDW
9h 18m
1 stop
Delta Logo
9:19 am - 9:20 pm
MDW
-
ANC
15h 01m
1 stop
$447Delta
Thu, Jul 23 - Sun, Aug 2
Delta Logo
10:30 pm - 6:31 pm
ANC
-
MDW
17h 01m
1 stop
Delta Logo
9:17 am - 9:16 pm
MDW
-
ANC
14h 59m
1 stop
$451Delta
Sun, Jun 21 - Sun, Jun 28
Delta Logo
10:30 pm - 6:31 pm
ANC
-
MDW
17h 01m
1 stop
Delta Logo
9:17 am - 8:52 pm
MDW
-
ANC
14h 35m
2 stops
$456Delta
Sun, Jun 21 - Sun, Jun 28

Delta flights from Anchorage to Chicago Midway Airport

Our best Delta deals on Anchorage to Chicago Midway Airport flight tickets
Delta
Aug 25
ANC6:00 amAnchorage
9h 01m
1 stop
MDW6:01 pmChicago Midway
Aug 29
MDW9:24 amChicago Midway
14h 32m
1 stop
ANC8:56 pmAnchorage
$393
Delta
Aug 25
ANC10:37 pmAnchorage
11h 02m
1 stop
MDW12:39 pmChicago Midway
Aug 29
MDW1:27 pmChicago Midway
13h 31m
2 stops
ANC11:58 pmAnchorage
$398
Delta
Nov 12
ANC2:20 pmAnchorage
15h 29m
2 stops
MDW8:49 amChicago Midway
Nov 16
MDW12:30 pmChicago Midway
13h 06m
2 stops
ANC10:36 pmAnchorage
$403

Southwest flights from Anchorage to Chicago Midway Airport

Our best Southwest deals on Anchorage to Chicago Midway Airport flight tickets
Southwest
Aug 25
ANC11:55 pmAnchorage
11h 50m
2 stops
MDW2:45 pmChicago Midway
Aug 29
MDW12:40 pmChicago Midway
13h 05m
2 stops
ANC10:45 pmAnchorage
$534
Southwest
Aug 18
ANC11:55 pmAnchorage
10h 40m
1 stop
MDW1:35 pmChicago Midway
Aug 24
MDW10:15 amChicago Midway
15h 30m
2 stops
ANC10:45 pmAnchorage
$548
Southwest
Aug 18
ANC11:55 pmAnchorage
11h 50m
2 stops
MDW2:45 pmChicago Midway
Aug 24
MDW10:15 amChicago Midway
15h 30m
2 stops
ANC10:45 pmAnchorage
$553

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 May 30, 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

Cheapest round-trip

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 8/25

6:00 am-6:01 pm

1 stop9h 01m

Chicago Midway

Sat 8/29

9:24 am-8:56 pm

1 stop14h 32m

$393

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 8/25

10:37 pm-12:39 pm

1 stop11h 02m

Chicago Midway

Sat 8/29

1:27 pm-11:58 pm

2 stops13h 31m

$398

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 11/12

2:20 pm-8:49 am

2 stops15h 29m

Chicago Midway

Mon 11/16

12:30 pm-10:36 pm

2 stops13h 06m

$403
Quickest round-trip

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 11/2

9:55 pm-8:49 am

1 stop7h 54m

Chicago Midway

Sat 11/7

12:30 pm-9:03 pm

1 stop11h 33m

$406

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 11/2

9:55 pm-8:49 am

1 stop7h 54m

Chicago Midway

Sat 11/7

9:30 am-9:03 pm

2 stops14h 33m

$411

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 6/21

10:30 pm-6:31 pm

1 stop17h 01m

Chicago Midway

Mon 6/29

6:58 pm-1:15 pm

2 stops21h 17m

$443

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 6/26

2:10 pm-8:37 am

2 stops15h 27m

Chicago Midway

Fri 7/3

9:17 am-11:20 pm

2 stops17h 03m

$444

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 7/23

6:00 am-6:18 pm

1 stop9h 18m

Chicago Midway

Sun 8/2

9:19 am-9:20 pm

1 stop15h 01m

$447

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 6/21

10:30 pm-6:31 pm

1 stop17h 01m

Chicago Midway

Sun 6/28

9:17 am-9:16 pm

1 stop14h 59m

$451

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 6/21

10:30 pm-6:31 pm

1 stop17h 01m

Chicago Midway

Sun 6/28

9:17 am-8:52 pm

2 stops14h 35m

$456

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 54m

Direct flights

None
The fastest flight from Anchorage to Chicago Midway Airport takes 7h 54m
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

Frequently asked questions about flying from Anchorage to Chicago Midway Airport

  • 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 54m.

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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