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.

$180 Cheap Flights from Chicago Midway Airport to Alaska in 2025/26

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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.

9:41 am - 10:49 pmMDW-ANC

16h 08m2 stops

6:05 am - 6:18 pmANC-MDW

9h 13m1 stop

$363Delta

Find Deal

Thu, Nov 20 - Wed, Nov 26

7:02 pm - 12:56 amMDW-ANC

8h 54m1 stop

6:05 am - 11:40 pmANC-MDW

14h 35m2 stops

$364Delta

Find Deal

Mon, Nov 24 - Thu, Nov 27

9:41 am - 10:49 pmMDW-ANC

16h 08m2 stops

6:05 am - 11:40 pmANC-MDW

14h 35m2 stops

$370Delta

Find Deal

Thu, Nov 20 - Wed, Nov 26

7:02 pm - 12:56 amMDW-ANC

8h 54m1 stop

6:05 am - 6:18 pmANC-MDW

9h 13m1 stop

$378Delta

Find Deal

Wed, Nov 26 - Wed, Dec 3

1:15 pm - 12:56 amMDW-ANC

14h 41m2 stops

6:05 am - 6:18 pmANC-MDW

9h 13m1 stop

$383Delta

Find Deal

Wed, Nov 26 - Wed, Dec 3

9:41 am - 6:46 pmMDW-ANC

12h 05m1 stop

12:30 am - 6:00 pmANC-MDW

14h 30m2 stops

$384Delta

Find Deal

Wed, Nov 26 - Tue, Dec 2

9:34 am - 10:45 pmMDW-ANC

16h 11m2 stops

12:30 am - 6:18 pmANC-MDW

14h 48m2 stops

$390Delta

Find Deal

Fri, Nov 28 - Thu, Dec 4

9:59 am - 12:18 amMDW-FAI

17h 19m2 stops

1:30 am - 6:18 pmFAI-MDW

13h 48m2 stops

$392Delta

Find Deal

Sat, Dec 6 - Fri, Dec 12

9:41 am - 6:46 pmMDW-ANC

12h 05m1 stop

9:45 pm - 9:19 amANC-MDW

8h 34m1 stop

$410Delta

Find Deal

Fri, Nov 28 - Fri, Dec 5

9:34 am - 10:45 pmMDW-ANC

16h 11m2 stops

9:45 pm - 9:19 amANC-MDW

8h 34m1 stop

$415Delta

Find Deal

Fri, Nov 28 - Mon, Dec 1

Delta flights from Chicago Midway Airport to Alaska

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

Delta

Nov 20

MDW9:41 amChicago Midway

16h 08m

2 stops

ANC10:49 pmAnchorage

Nov 26

ANC6:05 amAnchorage

9h 13m

1 stop

MDW6:18 pmChicago Midway

$363

Find similar

Delta

Nov 24

MDW7:02 pmChicago Midway

8h 54m

1 stop

ANC12:56 amAnchorage

Nov 27

ANC6:05 amAnchorage

14h 35m

2 stops

MDW11:40 pmChicago Midway

$364

Find similar

Delta

Nov 20

MDW9:41 amChicago Midway

16h 08m

2 stops

ANC10:49 pmAnchorage

Nov 26

ANC6:05 amAnchorage

14h 35m

2 stops

MDW11:40 pmChicago Midway

$370

Find similar

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

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 11/20

9:41 am-10:49 pm

2 stops16h 08m

Anchorage

Wed 11/26

6:05 am-6:18 pm

1 stop9h 13m

$363

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 11/24

7:02 pm-12:56 am

1 stop8h 54m

Anchorage

Thu 11/27

6:05 am-11:40 pm

2 stops14h 35m

$364

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 11/20

9:41 am-10:49 pm

2 stops16h 08m

Anchorage

Wed 11/26

6:05 am-11:40 pm

2 stops14h 35m

$370

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 11/26

7:02 pm-12:56 am

1 stop8h 54m

Anchorage

Wed 12/3

6:05 am-6:18 pm

1 stop9h 13m

$378

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 11/26

1:15 pm-12:56 am

2 stops14h 41m

Anchorage

Wed 12/3

6:05 am-6:18 pm

1 stop9h 13m

$383

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 11/26

9:41 am-6:46 pm

1 stop12h 05m

Anchorage

Tue 12/2

12:30 am-6:00 pm

2 stops14h 30m

$384

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 11/28

9:34 am-10:45 pm

2 stops16h 11m

Anchorage

Thu 12/4

12:30 am-6:18 pm

2 stops14h 48m

$390

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Sat 12/6

9:59 am-12:18 am

2 stops17h 19m

Fairbanks

Fri 12/12

1:30 am-6:18 pm

2 stops13h 48m

$392

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 11/28

9:41 am-6:46 pm

1 stop12h 05m

Anchorage

Fri 12/5

9:45 pm-9:19 am

1 stop8h 34m

$410

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Fri 11/28

9:34 am-10:45 pm

2 stops16h 11m

Anchorage

Mon 12/1

9:45 pm-9:19 am

1 stop8h 34m

$415

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

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

The cheapest day to depart from Chicago Midway Airport to Alaska is on a Tuesday. Travelers who choose to depart for Alaska on a Tuesday will often find tickets for as low as $514. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Alaska for around $630.

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

Our data shows that the cheapest Chicago Midway Airport to Alaska flights are usually those with departure times at noon. Our users have found flights to Alaska at noon for as low as $514. In the afternoon is when there is more demand to fly to Alaska, so prices are often more expensive at around $1,182 per ticket.

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

You could potentially save up to 27% 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

Direct flights	None

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

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.