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

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

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

Prices for flights from Chicago Midway Airport to Alaska refresh daily.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Alaska.

What documentation or ID do you need to fly to Alaska?

The required travel and health documents for your Alaska 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 Alaska. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$209 Cheap Flights from Chicago Midway Airport to Alaska in 2026

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Find the cheapest flights from Chicago Midway Airport to Alaska

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:29 am - 6:46 pm

MDW

ANC

12h 17m

1 stop

9:15 pm - 8:46 am

ANC

MDW

8h 31m

1 stop

$417Delta

Fri, Apr 24 - Mon, Apr 27

1:24 pm - 12:25 am

MDW

ANC

14h 01m

2 stops

9:15 pm - 8:46 am

ANC

MDW

8h 31m

1 stop

$422Delta

Tue, Apr 21 - Sat, Apr 25

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

9:54 am - 11:44 pm

MDW

ANC

16h 50m

2 stops

10:30 pm - 12:36 pm

ANC

MDW

11h 06m

1 stop

$428Delta

Tue, Jun 9 - Sun, Jun 14

1:49 pm - 1:23 am

MDW

ANC

14h 34m

1 stop

10:30 pm - 6:31 pm

ANC

MDW

17h 01m

1 stop

$429Delta

Fri, Jun 19 - Wed, Jun 24

1:59 pm - 8:49 pm

MDW

ANC

9h 50m

1 stop

6:00 am - 9:09 pm

ANC

MDW

12h 09m

2 stops

$430Delta

Mon, May 25 - Tue, Jun 2

1:16 pm - 1:55 am

MDW

ANC

15h 39m

2 stops

10:30 pm - 6:31 pm

ANC

MDW

17h 01m

1 stop

$434Delta

Thu, Jun 18 - Sun, Jun 21

1:22 pm - 12:31 am

MDW

ANC

14h 09m

2 stops

5:20 pm - 8:42 am

ANC

MDW

12h 22m

2 stops

$435Delta

Tue, May 26 - Thu, May 28

9:22 am - 8:16 pm

MDW

ANC

13h 54m

1 stop

12:05 am - 5:56 pm

ANC

MDW

14h 51m

2 stops

$436Delta

Mon, Jun 1 - Fri, Jun 5

Delta flights from Chicago Midway Airport to Alaska

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

Delta

Apr 24

MDW9:29 amChicago Midway

12h 17m

1 stop

ANC6:46 pmAnchorage

Apr 27

ANC9:15 pmAnchorage

8h 31m

1 stop

MDW8:46 amChicago Midway

$417

Delta

Apr 21

MDW1:24 pmChicago Midway

14h 01m

2 stops

ANC12:25 amAnchorage

Apr 25

ANC9:15 pmAnchorage

8h 31m

1 stop

MDW8:46 amChicago Midway

$422

Delta

Jun 9

MDW9:17 amChicago Midway

14h 59m

1 stop

ANC9:16 pmAnchorage

Jun 14

ANC10:30 pmAnchorage

11h 06m

1 stop

MDW12:36 pmChicago Midway

$423

Southwest flights from Chicago Midway Airport to Alaska

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

Southwest

May 27

MDW2:15 pmChicago Midway

11h 30m

1 stop

ANC10:45 pmAnchorage

May 31

ANC11:55 pmAnchorage

12h 20m

2 stops

MDW3:15 pmChicago Midway

$508

Southwest

May 25

MDW11:40 amChicago Midway

12h 35m

1 stop

ANC9:15 pmAnchorage

May 25

ANC10:25 pmAnchorage

8h 30m

1 stop

MDW9:55 amChicago Midway

$509

Southwest

May 25

MDW11:40 amChicago Midway

12h 35m

1 stop

ANC9:15 pmAnchorage

May 25

ANC10:25 pmAnchorage

12h 05m

2 stops

MDW1:30 pmChicago Midway

$514

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

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-8:46 am

1 stop8h 31m

$417

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 4/21

1:24 pm-12:25 am

2 stops14h 01m

Anchorage

Sat 4/25

9:15 pm-8:46 am

1 stop8h 31m

$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

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 6/9

9:54 am-11:44 pm

2 stops16h 50m

Anchorage

Sun 6/14

10:30 pm-12:36 pm

1 stop11h 06m

$428

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 6/19

1:49 pm-1:23 am

1 stop14h 34m

Anchorage

Wed 6/24

10:30 pm-6:31 pm

1 stop17h 01m

$429

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 5/25

1:59 pm-8:49 pm

1 stop9h 50m

Anchorage

Tue 6/2

6:00 am-9:09 pm

2 stops12h 09m

$430

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 6/18

1:16 pm-1:55 am

2 stops15h 39m

Anchorage

Sun 6/21

10:30 pm-6:31 pm

1 stop17h 01m

$434

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 5/26

1:22 pm-12:31 am

2 stops14h 09m

Anchorage

Thu 5/28

5:20 pm-8:42 am

2 stops12h 22m

$435

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 6/1

9:22 am-8:16 pm

1 stop13h 54m

Anchorage

Fri 6/5

12:05 am-5:56 pm

2 stops14h 51m

$436

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 Alaska

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

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

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

Cheap Chicago Midway Airport to Alaska flight deals and tips

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

Fastest flight time	9h 07m
Direct flights	None

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

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

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Alaska

When did momondo last update prices for flights from Chicago Midway Airport to Alaska?
Prices for flights from Chicago Midway Airport to Alaska refresh daily.
How old do you have to be to fly from Chicago Midway Airport to Alaska?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Alaska.
What documentation or ID do you need to fly to Alaska?
The required travel and health documents for your Alaska 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 Alaska. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Alaska for you.

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

Yes. momondo enables you to select and highlight flights to Alaska from Chicago with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Alaska from Chicago.

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

Yes momondo offers price alerts on flights to Alaska from Chicago. 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.