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.

$207 Cheap Flights from Chicago Midway Airport to Alaska in 2026

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.

9:59 am - 12:59 am

MDW

ANC

18h 00m

1 stop

12:54 pm - 8:39 am

ANC

MDW

16h 45m

1 stop

$407Delta

Sat, Sep 5 - Sun, Sep 6

7:25 pm - 12:59 am

MDW

ANC

8h 34m

1 stop

12:54 pm - 8:39 am

ANC

MDW

16h 45m

1 stop

$413Delta

Tue, Aug 18 - Fri, Aug 28

10:30 am - 10:45 pm

MDW

ANC

15h 15m

2 stops

11:55 pm - 1:30 pm

ANC

MDW

10h 35m

1 stop

$418Southwest

Tue, Aug 18 - Tue, Aug 25

9:24 am - 9:20 pm

MDW

ANC

14h 56m

1 stop

2:28 pm - 8:48 am

ANC

MDW

15h 20m

2 stops

$420Delta

Mon, Sep 7 - Sun, Sep 20

9:59 am - 8:49 pm

MDW

FAI

13h 50m

1 stop

10:00 pm - 8:39 am

FAI

MDW

7h 39m

1 stop

$422Delta

Fri, Aug 21 - Mon, Aug 24

10:30 am - 10:45 pm

MDW

ANC

15h 15m

2 stops

10:25 pm - 1:55 pm

ANC

MDW

12h 30m

2 stops

$423Southwest

Tue, Aug 18 - Tue, Aug 25

1:19 pm - 12:45 am

MDW

ANC

14h 26m

2 stops

10:10 pm - 12:39 pm

ANC

MDW

11h 29m

2 stops

$425Delta

Mon, Sep 21 - Mon, Sep 28

9:19 am - 9:20 pm

MDW

ANC

15h 01m

1 stop

10:30 pm - 4:59 pm

ANC

MDW

15h 29m

1 stop

$426Delta

Mon, Jul 27 - Sun, Aug 30

9:59 am - 8:49 pm

MDW

FAI

13h 50m

1 stop

10:00 pm - 12:39 pm

FAI

MDW

11h 39m

2 stops

$428Delta

Fri, Aug 21 - Mon, Aug 24

9:24 am - 8:49 pm

MDW

FAI

14h 25m

2 stops

10:00 pm - 12:39 pm

FAI

MDW

11h 39m

2 stops

$433Delta

Fri, Aug 21 - Mon, Aug 24

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Chicago Midway Airport to Alaska

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

Delta

Sep 5

MDW9:59 amChicago Midway

18h 00m

1 stop

ANC12:59 amAnchorage

Sep 6

ANC12:54 pmAnchorage

16h 45m

1 stop

MDW8:39 amChicago Midway

$407

Delta

Sep 7

MDW9:24 amChicago Midway

14h 56m

1 stop

ANC9:20 pmAnchorage

Sep 20

ANC2:28 pmAnchorage

15h 20m

2 stops

MDW8:48 amChicago Midway

$420

Delta

Aug 21

MDW9:59 amChicago Midway

13h 50m

1 stop

FAI8:49 pmFairbanks

Aug 24

FAI10:00 pmFairbanks

7h 39m

1 stop

MDW8:39 amChicago Midway

$422

Southwest flights from Chicago Midway Airport to Alaska

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

Southwest

Aug 18

MDW2:15 pmChicago Midway

10h 00m

1 stop

ANC9:15 pmAnchorage

Aug 25

ANC11:55 pmAnchorage

12h 10m

1 stop

MDW3:05 pmChicago Midway

$413

Southwest

Aug 18

MDW12:00 pmChicago Midway

12h 15m

1 stop

ANC9:15 pmAnchorage

Aug 25

ANC10:25 pmAnchorage

10h 25m

2 stops

MDW11:50 amChicago Midway

$418

Southwest

Aug 18

MDW10:30 amChicago Midway

15h 15m

2 stops

ANC10:45 pmAnchorage

Aug 25

ANC10:25 pmAnchorage

12h 30m

2 stops

MDW1:55 pmChicago Midway

$423

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

Sat 9/5

9:59 am-12:59 am

1 stop18h 00m

Anchorage

Sun 9/6

12:54 pm-8:39 am

1 stop16h 45m

$407

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 8/18

7:25 pm-12:59 am

1 stop8h 34m

Anchorage

Fri 8/28

12:54 pm-8:39 am

1 stop16h 45m

$413

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 8/18

10:30 am-10:45 pm

2 stops15h 15m

Anchorage

Tue 8/25

11:55 pm-1:30 pm

1 stop10h 35m

$418

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 9/7

9:24 am-9:20 pm

1 stop14h 56m

Anchorage

Sun 9/20

2:28 pm-8:48 am

2 stops15h 20m

$420

Quickest round-trip

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Fri 8/21

9:59 am-8:49 pm

1 stop13h 50m

Fairbanks

Mon 8/24

10:00 pm-8:39 am

1 stop7h 39m

$422

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 8/18

10:30 am-10:45 pm

2 stops15h 15m

Anchorage

Tue 8/25

10:25 pm-1:55 pm

2 stops12h 30m

$423

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 9/21

1:19 pm-12:45 am

2 stops14h 26m

Anchorage

Mon 9/28

10:10 pm-12:39 pm

2 stops11h 29m

$425

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 7/27

9:19 am-9:20 pm

1 stop15h 01m

Anchorage

Sun 8/30

10:30 pm-4:59 pm

1 stop15h 29m

$426

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Fri 8/21

9:59 am-8:49 pm

1 stop13h 50m

Fairbanks

Mon 8/24

10:00 pm-12:39 pm

2 stops11h 39m

$428

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Fri 8/21

9:24 am-8:49 pm

2 stops14h 25m

Fairbanks

Mon 8/24

10:00 pm-12:39 pm

2 stops11h 39m

$433

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 32% 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.

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.