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.

$230 Cheap Flights from Chicago Midway Airport to Alaska in 2026/27

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.

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

11h 32m1 stop Minneapolis St Paul

10:09 pm - 11:47 amANC Anchorage-MDW Chicago Midway

10h 38m1 stop Minneapolis St Paul

$459Delta

Sat, Oct 17 - Sat, Oct 24

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

11h 32m1 stop Minneapolis St Paul

10:08 pm - 11:50 amANC Anchorage-MDW Chicago Midway

10h 42m1 stop Minneapolis St Paul

$459Delta

Tue, Nov 3 - Tue, Nov 10

10:12 am - 8:59 pmMDW Chicago Midway-ANC Anchorage

13h 47m1 stop Minneapolis St Paul

10:08 pm - 8:50 amANC Anchorage-MDW Chicago Midway

7h 42m1 stop Minneapolis St Paul

$459Delta

Tue, Nov 3 - Tue, Nov 10

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

11h 32m1 stop Minneapolis St Paul

10:17 pm - 9:44 amANC Anchorage-MDW Chicago Midway

8h 27m1 stop Minneapolis St Paul

$459Delta

Sat, Oct 24 - Sat, Oct 31

9:29 am - 12:35 amMDW Chicago Midway-ANC Anchorage

18h 06m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

10:08 pm - 11:50 amANC Anchorage-MDW Chicago Midway

10h 42m1 stop Minneapolis St Paul

$464Delta

Tue, Nov 3 - Tue, Nov 10

9:29 am - 8:59 pmMDW Chicago Midway-ANC Anchorage

14h 30m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul

10:09 pm - 8:44 amANC Anchorage-MDW Chicago Midway

7h 35m1 stop Minneapolis St Paul

$464Delta

Sat, Oct 17 - Sat, Oct 24

1:27 pm - 12:35 amMDW Chicago Midway-ANC Anchorage

14h 08m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

10:08 pm - 8:50 amANC Anchorage-MDW Chicago Midway

7h 42m1 stop Minneapolis St Paul

$464Delta

Tue, Nov 3 - Tue, Nov 10

12:27 pm - 12:35 amMDW Chicago Midway-ANC Anchorage

15h 08m2 stops Minneapolis St Paul Seattle/Tacoma Intl

10:17 pm - 9:44 amANC Anchorage-MDW Chicago Midway

8h 27m1 stop Minneapolis St Paul

$464Delta

Sat, Oct 24 - Sat, Oct 31

12:30 pm - 1:39 amMDW Chicago Midway-ANC Anchorage

16h 09m2 stops Minneapolis St Paul Seattle/Tacoma Intl

10:05 pm - 8:55 amANC Anchorage-MDW Chicago Midway

7h 50m1 stop Minneapolis St Paul

$464Delta

Wed, Nov 11 - Wed, Dec 9

10:24 am - 12:37 amMDW Chicago Midway-FAI Fairbanks

17h 13m2 stops Minneapolis St Paul Seattle/Tacoma Intl

1:42 am - 4:50 pmFAI Fairbanks-MDW Chicago Midway

12h 08m2 stops Seattle/Tacoma Intl Minneapolis St Paul

$509Delta

Thu, Dec 3 - Sun, Dec 6

Cheap last minute flights

Enter your travel dates to find the best prices.

2:00 pm - 12:45 amMDW Chicago Midway-ANC Anchorage

13h 45m1 stop Minneapolis St Paul

10:17 pm - 12:47 pmANC Anchorage-MDW Chicago Midway

11h 30m1 stop Minneapolis St Paul

$529Delta

Thu, Oct 1 - Sat, Oct 31

9:29 am - 9:00 pmMDW Chicago Midway-ANC Anchorage

14h 31m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul

10:17 pm - 9:44 amANC Anchorage-MDW Chicago Midway

8h 27m1 stop Minneapolis St Paul

$534Delta

Thu, Oct 1 - Sat, Oct 31

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

10h 00m1 stop Minneapolis St Paul

10:09 pm - 8:44 amANC Anchorage-MDW Chicago Midway

7h 35m1 stop Minneapolis St Paul

$579Delta

Thu, Oct 1 - Sun, Oct 11

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

8h 32m1 stop Minneapolis St Paul

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

15h 38m1 stop Minneapolis St Paul

$579Delta

Fri, Oct 2 - Mon, Oct 12

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

10h 00m1 stop Minneapolis St Paul

10:09 pm - 11:47 amANC Anchorage-MDW Chicago Midway

10h 38m1 stop Minneapolis St Paul

$579Delta

Thu, Oct 1 - Sat, Oct 10

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

14h 01m1 stop Minneapolis St Paul

10:09 pm - 8:44 amANC Anchorage-MDW Chicago Midway

7h 35m1 stop Minneapolis St Paul

$579Delta

Fri, Oct 2 - Sat, Oct 10

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

14h 01m1 stop Minneapolis St Paul

10:09 pm - 8:44 amANC Anchorage-MDW Chicago Midway

7h 35m1 stop Minneapolis St Paul

$579Delta

Fri, Oct 2 - Sun, Oct 11

1:19 pm - 12:27 amMDW Chicago Midway-ANC Anchorage

14h 08m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

10:09 pm - 8:44 amANC Anchorage-MDW Chicago Midway

7h 35m1 stop Minneapolis St Paul

$584Delta

Thu, Oct 1 - Sat, Oct 10

9:29 am - 9:00 pmMDW Chicago Midway-ANC Anchorage

14h 31m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul

10:09 pm - 8:44 amANC Anchorage-MDW Chicago Midway

7h 35m1 stop Minneapolis St Paul

$584Delta

Fri, Oct 2 - Sun, Oct 11

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

10h 00m1 stop Minneapolis St Paul

4:05 pm - 8:44 amANC Anchorage-MDW Chicago Midway

13h 39m2 stops Seattle/Tacoma Intl Minneapolis St Paul

$606Delta

Sat, Oct 3 - Tue, Oct 6

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Delta flights from Chicago Midway Airport to Alaska

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

Delta

Oct 17

MDW12:27 pmChicago Midway

11h 32m

1 stop

ANC8:59 pmAnchorage

Oct 24

ANC10:09 pmAnchorage

7h 35m

1 stop

MDW8:44 amChicago Midway

$459

Delta

Nov 3

MDW1:27 pmChicago Midway

14h 08m

2 stops

ANC12:35 amAnchorage

Nov 10

ANC10:08 pmAnchorage

7h 42m

1 stop

MDW8:50 amChicago Midway

$464

Delta

Oct 17

MDW12:27 pmChicago Midway

11h 32m

1 stop

ANC8:59 pmAnchorage

Oct 23

ANC1:40 amAnchorage

12h 07m

2 stops

MDW4:47 pmChicago Midway

$466

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 Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Sat 10/17

12:27 pm-8:59 pm

1 stop11h 32m

Anchorage

Sat 10/24

10:09 pm-11:47 am

1 stop10h 38m

$459

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 11/3

12:27 pm-8:59 pm

1 stop11h 32m

Anchorage

Tue 11/10

10:08 pm-11:50 am

1 stop10h 42m

$459

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 11/3

10:12 am-8:59 pm

1 stop13h 47m

Anchorage

Tue 11/10

10:08 pm-8:50 am

1 stop7h 42m

$459

Quickest round-trip

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Sat 10/24

12:27 pm-8:59 pm

1 stop11h 32m

Anchorage

Sat 10/31

10:17 pm-9:44 am

1 stop8h 27m

$459

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 11/3

9:29 am-12:35 am

2 stops18h 06m

Anchorage

Tue 11/10

10:08 pm-11:50 am

1 stop10h 42m

$464

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Sat 10/17

9:29 am-8:59 pm

2 stops14h 30m

Anchorage

Sat 10/24

10:09 pm-8:44 am

1 stop7h 35m

$464

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 11/3

1:27 pm-12:35 am

2 stops14h 08m

Anchorage

Tue 11/10

10:08 pm-8:50 am

1 stop7h 42m

$464

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Sat 10/24

12:27 pm-12:35 am

2 stops15h 08m

Anchorage

Sat 10/31

10:17 pm-9:44 am

1 stop8h 27m

$464

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Wed 11/11

12:30 pm-1:39 am

2 stops16h 09m

Anchorage

Wed 12/9

10:05 pm-8:55 am

1 stop7h 50m

$464

ChicagoFairbanks

MDW Chicago Midway - FAI Fairbanks

MDWFAI

Chicago Midway

Thu 12/3

10:24 am-12:37 am

2 stops17h 13m

Fairbanks

Sun 12/6

1:42 am-4:50 pm

2 stops12h 08m

$509

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 13% 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

Best Price Found	$230
Fastest flight time	10h 15m
Direct flights	None

The best one-way flight to Alaska from Chicago Midway Airport in the past 72 hours is $230. The best round-trip flight deal from Chicago Midway Airport to Alaska found on momondo in the last 72 hours is $459.

The fastest flight from Chicago Midway Airport to Alaska takes 10h 15m

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.