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

Delta and Southwest are the most popular carriers 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.

$203 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.

1:49 pm - 10:21 am

MDW

ANC

23h 32m

2 stops

12:44 pm - 6:18 pm

ANC

MDW

26h 34m

1 stop

$400Delta

Mon, Jul 13 - Tue, Jul 21

9:49 am - 10:21 am

MDW

ANC

27h 32m

2 stops

12:44 pm - 8:37 am

ANC

MDW

16h 53m

1 stop

$401Delta

Sat, Jul 18 - Thu, Jul 23

9:49 am - 10:21 am

MDW

ANC

27h 32m

2 stops

12:44 pm - 6:18 pm

ANC

MDW

26h 34m

1 stop

$403Delta

Sat, Jul 18 - Tue, Jul 21

9:49 am - 1:17 pm

MDW

ANC

30h 28m

2 stops

6:00 am - 8:37 am

ANC

MDW

23h 37m

2 stops

$405Delta

Mon, Jul 13 - Thu, Jul 23

1:49 pm - 12:55 am

MDW

ANC

14h 06m

1 stop

6:00 am - 6:18 pm

ANC

MDW

9h 18m

1 stop

$406Delta

Sat, Jun 13 - Mon, Jun 15

9:19 am - 9:20 pm

MDW

ANC

15h 01m

1 stop

6:00 am - 1:09 pm

ANC

MDW

28h 09m

1 stop

$407Delta

Sun, Jul 26 - Mon, Jul 27

9:49 am - 10:21 am

MDW

ANC

27h 32m

2 stops

8:15 am - 8:37 am

ANC

MDW

21h 22m

2 stops

$408Delta

Sat, Jul 18 - Wed, Jul 22

1:26 pm - 12:55 am

MDW

ANC

14h 29m

2 stops

6:00 am - 6:18 pm

ANC

MDW

9h 18m

1 stop

$411Delta

Sat, Jun 13 - Mon, Jun 15

9:19 am - 9:20 pm

MDW

ANC

15h 01m

1 stop

1:30 am - 6:25 pm

ANC

MDW

13h 55m

2 stops

$413Delta

Sun, Jul 12 - Wed, Jul 15

12:20 pm - 11:45 pm

MDW

ANC

14h 25m

2 stops

12:55 am - 4:35 pm

ANC

MDW

12h 40m

2 stops

$416Southwest

Sun, Aug 23 - Tue, Sep 1

Delta flights from Chicago Midway Airport to Alaska

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

Delta

Jul 13

MDW1:49 pmChicago Midway

23h 32m

2 stops

ANC10:21 amAnchorage

Jul 21

ANC12:44 pmAnchorage

26h 34m

1 stop

MDW6:18 pmChicago Midway

$400

Delta

Jul 18

MDW9:49 amChicago Midway

27h 32m

2 stops

ANC10:21 amAnchorage

Jul 23

ANC12:44 pmAnchorage

16h 53m

1 stop

MDW8:37 amChicago Midway

$401

Delta

Jul 18

MDW9:49 amChicago Midway

27h 32m

2 stops

ANC10:21 amAnchorage

Jul 21

ANC12:44 pmAnchorage

26h 34m

1 stop

MDW6:18 pmChicago Midway

$403

Southwest flights from Chicago Midway Airport to Alaska

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

Southwest

Jun 20

MDW12:50 pmChicago Midway

11h 25m

2 stops

ANC9:15 pmAnchorage

Jun 29

ANC11:55 pmAnchorage

10h 55m

2 stops

MDW1:50 pmChicago Midway

$478

Southwest

May 21

MDW11:40 amChicago Midway

12h 35m

1 stop

ANC9:15 pmAnchorage

May 23

ANC10:25 pmAnchorage

10h 35m

1 stop

MDW12:00 pmChicago Midway

$559

Southwest

May 21

MDW11:40 amChicago Midway

12h 35m

1 stop

ANC9:15 pmAnchorage

May 23

ANC10:25 pmAnchorage

12h 15m

2 stops

MDW1:40 pmChicago Midway

$564

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

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 7/13

1:49 pm-10:21 am

2 stops23h 32m

Anchorage

Tue 7/21

12:44 pm-6:18 pm

1 stop26h 34m

$400

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 7/18

9:49 am-10:21 am

2 stops27h 32m

Anchorage

Thu 7/23

12:44 pm-8:37 am

1 stop16h 53m

$401

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 7/18

9:49 am-10:21 am

2 stops27h 32m

Anchorage

Tue 7/21

12:44 pm-6:18 pm

1 stop26h 34m

$403

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 7/13

9:49 am-1:17 pm

2 stops30h 28m

Anchorage

Thu 7/23

6:00 am-8:37 am

2 stops23h 37m

$405

Quickest round-trip

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 6/13

1:49 pm-12:55 am

1 stop14h 06m

Anchorage

Mon 6/15

6:00 am-6:18 pm

1 stop9h 18m

$406

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sun 7/26

9:19 am-9:20 pm

1 stop15h 01m

Anchorage

Mon 7/27

6:00 am-1:09 pm

1 stop28h 09m

$407

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 7/18

9:49 am-10:21 am

2 stops27h 32m

Anchorage

Wed 7/22

8:15 am-8:37 am

2 stops21h 22m

$408

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 6/13

1:26 pm-12:55 am

2 stops14h 29m

Anchorage

Mon 6/15

6:00 am-6:18 pm

1 stop9h 18m

$411

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sun 7/12

9:19 am-9:20 pm

1 stop15h 01m

Anchorage

Wed 7/15

1:30 am-6:25 pm

2 stops13h 55m

$413

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sun 8/23

12:20 pm-11:45 pm

2 stops14h 25m

Anchorage

Tue 9/1

12:55 am-4:35 pm

2 stops12h 40m

$416

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 5% 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	8h 34m
Direct flights	None

The fastest flight from Chicago Midway Airport to Alaska takes 8h 34m

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

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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.