Cheap flights from Anchorage to Chicago from $168

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 10/26. 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 (ANC-MDW)

Cheap round-trip flights

Delta Logo
10:00 pm - 8:53 amANC-MDW
7h 53m1 stop
Delta Logo
7:15 pm - 1:36 amMDW-ANC
9h 21m1 stop
$338Delta
Find Deal
Fri, Sep 26 - Mon, Sep 29
Delta Logo
12:55 am - 6:35 pmANC-MDW
14h 40m2 stops
Delta Logo
7:15 pm - 1:36 amMDW-ANC
9h 21m1 stop
$343Delta
Find Deal
Thu, Sep 25 - Mon, Sep 29
Delta Logo
5:15 pm - 8:53 amANC-MDW
12h 38m2 stops
Delta Logo
1:08 pm - 1:37 amMDW-ANC
15h 29m2 stops
$348Delta
Find Deal
Thu, Sep 25 - Thu, Oct 2
Delta Logo
12:30 am - 8:40 amANC-MDW
29h 10m2 stops
Delta Logo
7:10 pm - 12:51 amMDW-ANC
8h 41m1 stop
$375Delta
Find Deal
Wed, Oct 22 - Mon, Oct 27
Delta Logo
12:30 am - 8:40 amANC-MDW
29h 10m2 stops
Delta Logo
1:08 pm - 1:59 amMDW-ANC
15h 51m2 stops
$380Delta
Find Deal
Wed, Oct 22 - Mon, Oct 27
Delta Logo
10:00 pm - 8:49 amANC-MDW
7h 49m1 stop
Delta Logo
7:15 pm - 1:36 amMDW-ANC
9h 21m1 stop
$400Delta
Find Deal
Sat, Sep 20 - Mon, Sep 22
Delta Logo
6:05 am - 5:43 pmANC-MDW
8h 38m1 stop
Delta Logo
7:02 pm - 12:56 amMDW-ANC
8h 54m1 stop
$402Delta
Find Deal
Thu, Nov 6 - Sun, Nov 9
Delta Logo
12:55 am - 6:35 pmANC-MDW
14h 40m2 stops
Delta Logo
1:43 pm - 6:53 pmMDW-ANC
8h 10m1 stop
$405Delta
Find Deal
Wed, Sep 24 - Thu, Oct 2
Delta Logo
12:55 am - 6:35 pmANC-MDW
14h 40m2 stops
Delta Logo
1:08 pm - 1:37 amMDW-ANC
15h 29m2 stops
$410Delta
Find Deal
Tue, Sep 30 - Sun, Oct 5
Delta Logo
12:30 am - 6:25 pmANC-MDW
14h 55m2 stops
Delta Logo
7:02 pm - 12:56 amMDW-ANC
8h 54m1 stop
$437Delta
Find Deal
Wed, Nov 5 - Sun, Nov 9

Delta flights from Anchorage to Chicago Midway Airport

Our best Delta deals on Anchorage to Chicago Midway Airport flight tickets
Delta
Sep 26
ANC10:00 pmAnchorage
7h 53m
1 stop
MDW8:53 amChicago Midway
Sep 29
MDW7:15 pmChicago Midway
9h 21m
1 stop
ANC1:36 amAnchorage
Delta
Sep 25
ANC12:55 amAnchorage
14h 40m
2 stops
MDW6:35 pmChicago Midway
Sep 29
MDW7:15 pmChicago Midway
9h 21m
1 stop
ANC1:36 amAnchorage
Delta
Sep 25
ANC5:15 pmAnchorage
12h 38m
2 stops
MDW8:53 amChicago Midway
Oct 2
MDW1:08 pmChicago Midway
15h 29m
2 stops
ANC1:37 amAnchorage

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 August 28, 2025.
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

Fri 9/26

10:00 pm-8:53 am

1 stop7h 53m

Chicago Midway

Mon 9/29

7:15 pm-1:36 am

1 stop9h 21m

$338

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 9/25

12:55 am-6:35 pm

2 stops14h 40m

Chicago Midway

Mon 9/29

7:15 pm-1:36 am

1 stop9h 21m

$343

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 9/25

5:15 pm-8:53 am

2 stops12h 38m

Chicago Midway

Thu 10/2

1:08 pm-1:37 am

2 stops15h 29m

$348

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 10/22

12:30 am-8:40 am

2 stops29h 10m

Chicago Midway

Mon 10/27

7:10 pm-12:51 am

1 stop8h 41m

$375

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 10/22

12:30 am-8:40 am

2 stops29h 10m

Chicago Midway

Mon 10/27

1:08 pm-1:59 am

2 stops15h 51m

$380

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 9/20

10:00 pm-8:49 am

1 stop7h 49m

Chicago Midway

Mon 9/22

7:15 pm-1:36 am

1 stop9h 21m

$400

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 11/6

6:05 am-5:43 pm

1 stop8h 38m

Chicago Midway

Sun 11/9

7:02 pm-12:56 am

1 stop8h 54m

$402

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 9/24

12:55 am-6:35 pm

2 stops14h 40m

Chicago Midway

Thu 10/2

1:43 pm-6:53 pm

1 stop8h 10m

$405

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 9/30

12:55 am-6:35 pm

2 stops14h 40m

Chicago Midway

Sun 10/5

1:08 pm-1:37 am

2 stops15h 29m

$410

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 11/5

12:30 am-6:25 pm

2 stops14h 55m

Chicago Midway

Sun 11/9

7:02 pm-12:56 am

1 stop8h 54m

$437

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

Direct flights

None
There are no direct flights from Anchorage to Chicago Midway Airport. There are no popular flight routes 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 48m.

  • 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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.

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1 adult
Tue 9/2
Tue 9/9

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