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.

$222 Cheap Flights from Chicago Midway Airport to Anchorage in 2026

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.

9:59 am - 9:00 pmMDW Chicago Midway-ANC Anchorage

14h 01m1 stop Minneapolis St Paul

6:00 am - 6:19 pmANC Anchorage-MDW Chicago Midway

9h 19m1 stop Minneapolis St Paul

$437Delta

Tue, Sep 22 - Wed, Sep 23

9:59 am - 9:00 pmMDW Chicago Midway-ANC Anchorage

14h 01m1 stop Minneapolis St Paul

6:00 am - 6:19 pmANC Anchorage-MDW Chicago Midway

9h 19m1 stop Minneapolis St Paul

$437Delta

Tue, Sep 29 - Wed, Sep 30

2:00 pm - 12:27 amMDW Chicago Midway-ANC Anchorage

13h 27m2 stops Minneapolis St Paul Seattle/Tacoma Intl

6:00 am - 6:19 pmANC Anchorage-MDW Chicago Midway

9h 19m1 stop Minneapolis St Paul

$442Delta

Tue, Sep 22 - Wed, Sep 23

2:00 pm - 12:27 amMDW Chicago Midway-ANC Anchorage

13h 27m2 stops Minneapolis St Paul Seattle/Tacoma Intl

6:00 am - 6:19 pmANC Anchorage-MDW Chicago Midway

9h 19m1 stop Minneapolis St Paul

$442Delta

Tue, Sep 29 - Wed, Sep 30

7:13 pm - 12:45 amMDW Chicago Midway-ANC Anchorage

8h 32m1 stop Minneapolis St Paul

10:10 pm - 8:48 amANC Anchorage-MDW Chicago Midway

7h 38m1 stop Minneapolis St Paul

$443Delta

Mon, Sep 14 - Mon, Sep 21

2:00 pm - 9:00 pmMDW Chicago Midway-ANC Anchorage

10h 00m1 stop Minneapolis St Paul

6:00 am - 6:19 pmANC Anchorage-MDW Chicago Midway

9h 19m1 stop Minneapolis St Paul

$443Delta

Wed, Sep 16 - Wed, Sep 30

12:27 pm - 8:59 pmMDW Chicago Midway-ANC Anchorage

11h 32m1 stop Minneapolis St Paul

10:09 pm - 4:47 pmANC Anchorage-MDW Chicago Midway

15h 38m1 stop Minneapolis St Paul

$443Delta

Fri, Oct 23 - Mon, Oct 26

9:59 am - 9:00 pmMDW Chicago Midway-ANC Anchorage

14h 01m1 stop Minneapolis St Paul

8:05 pm - 11:54 amANC Anchorage-MDW Chicago Midway

12h 49m1 stop Atlanta Hartsfield-Jackson

$443Delta

Wed, Sep 23 - Sat, Sep 26

7:13 pm - 12:45 amMDW Chicago Midway-ANC Anchorage

8h 32m1 stop Minneapolis St Paul

10:10 pm - 8:48 amANC Anchorage-MDW Chicago Midway

7h 38m1 stop Minneapolis St Paul

$443Delta

Fri, Sep 25 - Tue, Sep 29

2:00 pm - 9:00 pmMDW Chicago Midway-ANC Anchorage

10h 00m1 stop Minneapolis St Paul

6:00 am - 6:19 pmANC Anchorage-MDW Chicago Midway

9h 19m1 stop Minneapolis St Paul

$443Delta

Sat, Sep 19 - Tue, Sep 29

Cheap last minute flights

Enter your travel dates to find the best prices.

7:25 pm - 12:59 amMDW Chicago Midway-ANC Anchorage

8h 34m1 stop Minneapolis St Paul

10:30 pm - 12:39 pmANC Anchorage-MDW Chicago Midway

11h 09m1 stop Detroit Metropolitan Wayne County

$519Delta

Fri, Aug 14 - Mon, Aug 17

7:25 pm - 12:59 amMDW Chicago Midway-ANC Anchorage

8h 34m1 stop Minneapolis St Paul

6:00 am - 6:01 pmANC Anchorage-MDW Chicago Midway

9h 01m1 stop Minneapolis St Paul

$519Delta

Fri, Aug 14 - Mon, Aug 17

6:05 am - 7:00 pmMDW Chicago Midway-ANC Anchorage

15h 55m1 stop Atlanta Hartsfield-Jackson

10:30 pm - 12:39 pmANC Anchorage-MDW Chicago Midway

11h 09m1 stop Detroit Metropolitan Wayne County

$519Delta

Sun, Aug 16 - Sat, Aug 22

1:25 pm - 9:20 pmMDW Chicago Midway-ANC Anchorage

10h 55m1 stop Detroit Metropolitan Wayne County

8:20 pm - 11:51 amANC Anchorage-MDW Chicago Midway

12h 31m1 stop Atlanta Hartsfield-Jackson

$519Delta

Mon, Aug 17 - Mon, Aug 24

1:25 pm - 11:24 pmMDW Chicago Midway-ANC Anchorage

12h 59m2 stops Detroit Metropolitan Wayne County Salt Lake City

10:30 pm - 12:39 pmANC Anchorage-MDW Chicago Midway

11h 09m1 stop Detroit Metropolitan Wayne County

$524Delta

Fri, Aug 14 - Mon, Aug 17

1:25 pm - 11:55 pmMDW Chicago Midway-ANC Anchorage

13h 30m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

10:30 pm - 12:39 pmANC Anchorage-MDW Chicago Midway

11h 09m1 stop Detroit Metropolitan Wayne County

$524Delta

Fri, Aug 14 - Mon, Aug 17

1:25 pm - 11:24 pmMDW Chicago Midway-ANC Anchorage

12h 59m2 stops Detroit Metropolitan Wayne County Salt Lake City

10:10 pm - 1:10 pmANC Anchorage-MDW Chicago Midway

12h 00m1 stop Minneapolis St Paul

$524Delta

Fri, Aug 14 - Mon, Aug 17

6:05 am - 7:00 pmMDW Chicago Midway-ANC Anchorage

15h 55m1 stop Atlanta Hartsfield-Jackson

6:00 am - 10:36 pmANC Anchorage-MDW Chicago Midway

13h 36m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

$526Delta

Sun, Aug 16 - Sat, Aug 22

1:51 pm - 9:00 pmMDW Chicago Midway-ANC Anchorage

10h 09m1 stop Minneapolis St Paul

10:30 pm - 12:39 pmANC Anchorage-MDW Chicago Midway

11h 09m1 stop Detroit Metropolitan Wayne County

$561Delta

Fri, Aug 14 - Mon, Aug 17

12:15 pm - 10:45 pmMDW Chicago Midway-ANC Anchorage

13h 30m1 stop Las Vegas Harry Reid Intl

10:25 pm - 4:10 pmANC Anchorage-MDW Chicago Midway

14h 45m1 stop Denver Intl

$685Southwest

Sun, Aug 16 - Wed, Aug 19

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Delta flights from Chicago Midway Airport to Anchorage

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

Delta

Sep 22

MDW9:59 amChicago Midway

14h 01m

1 stop

ANC9:00 pmAnchorage

Sep 23

ANC6:00 amAnchorage

9h 19m

1 stop

MDW6:19 pmChicago Midway

$437

Delta

Sep 22

MDW2:00 pmChicago Midway

13h 27m

2 stops

ANC12:27 amAnchorage

Sep 23

ANC6:00 amAnchorage

9h 19m

1 stop

MDW6:19 pmChicago Midway

$442

Delta

Sep 14

MDW9:59 amChicago Midway

14h 01m

1 stop

ANC9:00 pmAnchorage

Sep 24

ANC6:00 amAnchorage

9h 19m

1 stop

MDW6:19 pmChicago Midway

$443

Southwest flights from Chicago Midway Airport to Anchorage

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

Southwest

Aug 31

MDW10:15 amChicago Midway

15h 30m

2 stops

ANC10:45 pmAnchorage

Sep 4

ANC11:55 pmAnchorage

13h 25m

1 stop

MDW4:20 pmChicago Midway

$603

Southwest

Aug 27

MDW10:15 amChicago Midway

15h 30m

2 stops

ANC10:45 pmAnchorage

Sep 1

ANC11:55 pmAnchorage

10h 35m

1 stop

MDW1:30 pmChicago Midway

$614

Southwest

Aug 23

MDW12:20 pmChicago Midway

13h 25m

2 stops

ANC10:45 pmAnchorage

Sep 2

ANC11:55 pmAnchorage

13h 15m

2 stops

MDW4:10 pmChicago Midway

$646

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 Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 9/22

9:59 am-9:00 pm

1 stop14h 01m

Anchorage

Wed 9/23

6:00 am-6:19 pm

1 stop9h 19m

$437

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 9/29

9:59 am-9:00 pm

1 stop14h 01m

Anchorage

Wed 9/30

6:00 am-6:19 pm

1 stop9h 19m

$437

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 9/22

2:00 pm-12:27 am

2 stops13h 27m

Anchorage

Wed 9/23

6:00 am-6:19 pm

1 stop9h 19m

$442

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 9/29

2:00 pm-12:27 am

2 stops13h 27m

Anchorage

Wed 9/30

6:00 am-6:19 pm

1 stop9h 19m

$442

Quickest round-trip

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Mon 9/14

7:13 pm-12:45 am

1 stop8h 32m

Anchorage

Mon 9/21

10:10 pm-8:48 am

1 stop7h 38m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Wed 9/16

2:00 pm-9:00 pm

1 stop10h 00m

Anchorage

Wed 9/30

6:00 am-6:19 pm

1 stop9h 19m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Fri 10/23

12:27 pm-8:59 pm

1 stop11h 32m

Anchorage

Mon 10/26

10:09 pm-4:47 pm

1 stop15h 38m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Wed 9/23

9:59 am-9:00 pm

1 stop14h 01m

Anchorage

Sat 9/26

8:05 pm-11:54 am

1 stop12h 49m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Fri 9/25

7:13 pm-12:45 am

1 stop8h 32m

Anchorage

Tue 9/29

10:10 pm-8:48 am

1 stop7h 38m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Sat 9/19

2:00 pm-9:00 pm

1 stop10h 00m

Anchorage

Tue 9/29

6:00 am-6:19 pm

1 stop9h 19m

$443

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 $612.

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

In the afternoon is the cheapest time of day to fly from Chicago Midway Airport to Anchorage when you can find flight prices for as low as $496. Flying to Anchorage in the afternoon is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $868.

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

You could potentially save up to 13% 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	8h 32m
Direct flights	None

The fastest flight from Chicago Midway Airport to Anchorage takes 8h 32m

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 8h 32m, 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

Palmer

Talkeetna

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.