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

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

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

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

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

What documentation or ID do you need to fly to Anchorage Airport?

The required travel and health documents for your Anchorage Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Anchorage Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$199 Cheap Flights from Chicago Midway Airport to Anchorage in 2026

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Find the cheapest flights from Chicago Midway Airport to Anchorage

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:22 am - 8:16 pm

MDW

ANC

13h 54m

1 stop

6:00 am - 5:56 pm

ANC

MDW

8h 56m

1 stop

$391Delta

Sun, May 31 - Mon, Jun 1

1:59 pm - 12:31 am

MDW

ANC

13h 32m

1 stop

9:59 pm - 8:42 am

ANC

MDW

7h 43m

1 stop

$397Delta

Wed, May 27 - Mon, Jun 1

1:22 pm - 12:50 am

MDW

ANC

14h 28m

2 stops

9:59 pm - 8:42 am

ANC

MDW

7h 43m

1 stop

$402Delta

Wed, May 13 - Mon, May 18

9:46 am - 6:46 pm

MDW

ANC

12h 00m

1 stop

1:41 pm - 8:47 am

ANC

MDW

16h 06m

2 stops

$404Delta

Sat, Apr 25 - Fri, May 1

1:22 pm - 12:50 am

MDW

ANC

14h 28m

2 stops

5:20 pm - 8:42 am

ANC

MDW

12h 22m

2 stops

$409Delta

Wed, May 13 - Mon, May 18

9:22 am - 8:16 pm

MDW

ANC

13h 54m

1 stop

10:02 pm - 8:37 am

ANC

MDW

7h 35m

1 stop

$413Delta

Sun, May 24 - Wed, Jun 10

9:22 am - 8:16 pm

MDW

ANC

13h 54m

1 stop

9:30 pm - 8:43 am

ANC

MDW

8h 13m

1 stop

$417Delta

Fri, May 29 - Wed, Jun 3

1:22 pm - 11:20 pm

MDW

ANC

12h 58m

2 stops

9:30 pm - 8:43 am

ANC

MDW

8h 13m

1 stop

$422Delta

Fri, May 29 - Wed, Jun 3

9:17 am - 9:16 pm

MDW

ANC

14h 59m

1 stop

10:30 pm - 12:36 pm

ANC

MDW

11h 06m

1 stop

$423Delta

Tue, Jun 9 - Sun, Jun 14

9:29 am - 6:46 pm

MDW

ANC

12h 17m

1 stop

9:15 pm - 12:43 pm

ANC

MDW

12h 28m

2 stops

$424Delta

Fri, Apr 24 - Mon, Apr 27

Southwest flights from Chicago Midway Airport to Anchorage

Our best Southwest deals on Chicago Midway Airport to Anchorage flight tickets

Southwest

May 28

MDW12:35 pmChicago Midway

13h 10m

2 stops

ANC10:45 pmAnchorage

Jun 2

ANC11:55 pmAnchorage

13h 00m

2 stops

MDW3:55 pmChicago Midway

$477

Southwest

May 25

MDW12:35 pmChicago Midway

13h 10m

2 stops

ANC10:45 pmAnchorage

Jun 2

ANC11:55 pmAnchorage

11h 15m

1 stop

MDW2:10 pmChicago Midway

$491

Southwest

May 26

MDW12:35 pmChicago Midway

11h 40m

1 stop

ANC9:15 pmAnchorage

May 28

ANC10:25 pmAnchorage

8h 30m

1 stop

MDW9:55 amChicago Midway

$509

Delta flights from Chicago Midway Airport to Anchorage

Our best Delta deals on Chicago Midway Airport to Anchorage flight tickets

Delta

May 31

MDW9:22 amChicago Midway

13h 54m

1 stop

ANC8:16 pmAnchorage

Jun 1

ANC6:00 amAnchorage

8h 56m

1 stop

MDW5:56 pmChicago Midway

$391

Delta

May 27

MDW1:59 pmChicago Midway

13h 32m

1 stop

ANC12:31 amAnchorage

May 31

ANC9:30 pmAnchorage

12h 12m

1 stop

MDW12:42 pmChicago Midway

$397

Delta

May 13

MDW1:22 pmChicago Midway

14h 28m

2 stops

ANC12:50 amAnchorage

May 18

ANC9:59 pmAnchorage

7h 43m

1 stop

MDW8:42 amChicago Midway

$402

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Anchorage that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sun 5/31

9:22 am-8:16 pm

1 stop13h 54m

Anchorage

Mon 6/1

6:00 am-5:56 pm

1 stop8h 56m

$391

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 5/27

1:59 pm-12:31 am

1 stop13h 32m

Anchorage

Mon 6/1

9:59 pm-8:42 am

1 stop7h 43m

$397

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 5/13

1:22 pm-12:50 am

2 stops14h 28m

Anchorage

Mon 5/18

9:59 pm-8:42 am

1 stop7h 43m

$402

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 4/25

9:46 am-6:46 pm

1 stop12h 00m

Anchorage

Fri 5/1

1:41 pm-8:47 am

2 stops16h 06m

$404

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 5/13

1:22 pm-12:50 am

2 stops14h 28m

Anchorage

Mon 5/18

5:20 pm-8:42 am

2 stops12h 22m

$409

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sun 5/24

9:22 am-8:16 pm

1 stop13h 54m

Anchorage

Wed 6/10

10:02 pm-8:37 am

1 stop7h 35m

$413

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 5/29

9:22 am-8:16 pm

1 stop13h 54m

Anchorage

Wed 6/3

9:30 pm-8:43 am

1 stop8h 13m

$417

Quickest round-trip

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 5/29

1:22 pm-11:20 pm

2 stops12h 58m

Anchorage

Wed 6/3

9:30 pm-8:43 am

1 stop8h 13m

$422

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 6/9

9:17 am-9:16 pm

1 stop14h 59m

Anchorage

Sun 6/14

10:30 pm-12:36 pm

1 stop11h 06m

$423

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 4/24

9:29 am-6:46 pm

1 stop12h 17m

Anchorage

Mon 4/27

9:15 pm-12:43 pm

2 stops12h 28m

$424

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

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

Prices

Airlines

What is the cheapest day to depart on your flight to Anchorage?

The cheapest day to depart on your flight to Anchorage is on a Wednesday when prices can be found for as low as $496. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Anchorage is Saturday, with ticket prices averaging around $610.

What is the cheapest time of day to depart on your flight to Anchorage?

At noon is the cheapest time of day to fly from Chicago Midway Airport to Anchorage when you can find flight prices for as low as $456. Flying to Anchorage at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $572.

Can stopping save me money on Chicago Midway Airport to Anchorage flights?

You could potentially save up to 16% on your flight if you consider stops on a Chicago Midway Airport to Anchorage flight.

When to book flights from Chicago Midway Airport to Anchorage

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

Estimated round-trip price

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

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

Fastest flight time	9h 07m
Direct flights	None

The fastest flight from Chicago Midway Airport to Anchorage takes 9h 07m

There are no direct flights from Chicago Midway Airport to Anchorage. There are no popular flight routes from Chicago Midway Airport to Anchorage.

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Anchorage

How far is Chicago Midway to Anchorage by plane?
The straight-line distance from Chicago Midway to Anchorage is 2848.8 mi. Flights usually cover this in 9h 07m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to Anchorage Airport?
Prices for flights from Chicago Midway Airport to Anchorage Airport were last updated today.
How old do you have to be to fly from Chicago Midway Airport to Anchorage 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 Chicago Midway Airport to Anchorage Airport.
What documentation or ID do you need to fly to Anchorage Airport?
The required travel and health documents for your Anchorage Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Anchorage Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Seward

Wasilla

Talkeetna

Palmer

Girdwood

Eagle River

Why use momondo?

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

It is quick and easy to find Chicago to Anchorage flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Anchorage that suits you.

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

Flights from Chicago to Anchorage with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Chicago to Anchorage flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Chicago to Anchorage now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Anchorage and let you know when they change.