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.

$222 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.

10:01 am - 8:59 pmMDW Chicago Midway-ANC Anchorage

13h 58m1 stop Minneapolis St Paul

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

10h 38m1 stop Minneapolis St Paul

$443Delta

Tue, Oct 20 - Tue, Oct 27

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

11h 32m1 stop Minneapolis St Paul

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

7h 35m1 stop Minneapolis St Paul

$443Delta

Wed, Oct 21 - Mon, Oct 26

9:55 am - 9:03 pmMDW Chicago Midway-ANC Anchorage

14h 08m1 stop Minneapolis St Paul

9:55 pm - 8:49 amANC Anchorage-MDW Chicago Midway

7h 54m1 stop Minneapolis St Paul

$443Delta

Tue, Jan 26 - Mon, Feb 1

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

10h 00m1 stop Minneapolis St Paul

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

7h 34m1 stop Minneapolis St Paul

$443Delta

Mon, Sep 28 - Mon, Oct 5

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

10h 00m1 stop Minneapolis St Paul

6:00 am - 6:19 pmANC Anchorage-MDW Chicago Midway

9h 19m1 stop Minneapolis St Paul

$443Delta

Wed, Sep 16 - Wed, Sep 30

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

10h 00m1 stop Minneapolis St Paul

10:10 pm - 8:48 amANC Anchorage-MDW Chicago Midway

7h 38m1 stop Minneapolis St Paul

$443Delta

Tue, Sep 15 - Mon, Sep 28

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

11h 32m1 stop Minneapolis St Paul

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

7h 35m1 stop Minneapolis St Paul

$443Delta

Wed, Oct 21 - Wed, Oct 28

10:01 am - 8:59 pmMDW Chicago Midway-ANC Anchorage

13h 58m1 stop Minneapolis St Paul

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

10h 38m1 stop Minneapolis St Paul

$443Delta

Tue, Oct 20 - Wed, Oct 28

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

11h 32m1 stop Minneapolis St Paul

10:06 pm - 8:50 amANC Anchorage-MDW Chicago Midway

7h 44m1 stop Minneapolis St Paul

$443Delta

Tue, Nov 3 - Tue, Nov 10

9:55 am - 12:15 amMDW Chicago Midway-FAI Fairbanks

17h 20m2 stops Minneapolis St Paul Seattle/Tacoma Intl

1:30 am - 4:50 pmFAI Fairbanks-MDW Chicago Midway

12h 20m2 stops Seattle/Tacoma Intl Minneapolis St Paul

$535Delta

Fri, Jan 29 - Fri, Feb 5

Cheap last minute flights

Enter your travel dates to find the best prices.

9:59 am - 12:59 amMDW Chicago Midway-ANC Anchorage

18h 00m1 stop Minneapolis St Paul

12:54 pm - 8:39 amANC Anchorage-MDW Chicago Midway

16h 45m1 stop Minneapolis St Paul

$513Delta

Thu, Aug 20 - Fri, Aug 21

7:25 pm - 12:59 amMDW Chicago Midway-ANC Anchorage

8h 34m1 stop Minneapolis St Paul

12:54 pm - 8:39 amANC Anchorage-MDW Chicago Midway

16h 45m1 stop Minneapolis St Paul

$513Delta

Fri, Aug 21 - Sat, Aug 22

7:25 pm - 12:59 amMDW Chicago Midway-ANC Anchorage

8h 34m1 stop Minneapolis St Paul

10:30 pm - 12:39 pmANC Anchorage-MDW Chicago Midway

11h 09m1 stop Detroit Metropolitan Wayne County

$519Delta

Fri, Aug 21 - Mon, Aug 24

1:25 pm - 9:20 pmMDW Chicago Midway-ANC Anchorage

10h 55m1 stop Detroit Metropolitan Wayne County

6:00 am - 6:01 pmANC Anchorage-MDW Chicago Midway

9h 01m1 stop Minneapolis St Paul

$519Delta

Fri, Aug 21 - Fri, Aug 28

9:24 am - 9:20 pmMDW Chicago Midway-ANC Anchorage

14h 56m1 stop Detroit Metropolitan Wayne County

8:20 pm - 11:51 amANC Anchorage-MDW Chicago Midway

12h 31m1 stop Atlanta Hartsfield-Jackson

$519Delta

Fri, Aug 21 - Mon, Aug 24

1:25 pm - 9:20 pmMDW Chicago Midway-ANC Anchorage

10h 55m1 stop Detroit Metropolitan Wayne County

6:00 am - 6:01 pmANC Anchorage-MDW Chicago Midway

9h 01m1 stop Minneapolis St Paul

$519Delta

Thu, Aug 20 - Tue, Aug 25

1:25 pm - 9:20 pmMDW Chicago Midway-ANC Anchorage

10h 55m1 stop Detroit Metropolitan Wayne County

10:10 pm - 1:10 pmANC Anchorage-MDW Chicago Midway

12h 00m1 stop Minneapolis St Paul

$519Delta

Wed, Aug 19 - Tue, Aug 25

10:54 am - 7:00 pmMDW Chicago Midway-ANC Anchorage

11h 06m1 stop Atlanta Hartsfield-Jackson

6:00 am - 6:01 pmANC Anchorage-MDW Chicago Midway

9h 01m1 stop Minneapolis St Paul

$519Delta

Wed, Aug 19 - Thu, Aug 27

1:25 pm - 9:20 pmMDW Chicago Midway-ANC Anchorage

10h 55m1 stop Detroit Metropolitan Wayne County

10:30 pm - 12:39 pmANC Anchorage-MDW Chicago Midway

11h 09m1 stop Detroit Metropolitan Wayne County

$519Delta

Wed, Aug 19 - Sat, Aug 22

9:24 am - 9:20 pmMDW Chicago Midway-ANC Anchorage

14h 56m1 stop Detroit Metropolitan Wayne County

6:00 am - 6:01 pmANC Anchorage-MDW Chicago Midway

9h 01m1 stop Minneapolis St Paul

$519Delta

Fri, Aug 21 - Sun, Aug 30

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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

Sep 28

MDW2:00 pmChicago Midway

10h 00m

1 stop

ANC9:00 pmAnchorage

Oct 5

ANC10:10 pmAnchorage

7h 34m

1 stop

MDW8:44 amChicago Midway

$443

Delta

Nov 3

MDW6:04 amChicago Midway

17h 55m

2 stops

ANC8:59 pmAnchorage

Nov 10

ANC10:06 pmAnchorage

7h 44m

1 stop

MDW8:50 amChicago Midway

$448

Delta

Sep 28

MDW2:00 pmChicago Midway

10h 00m

1 stop

ANC9:00 pmAnchorage

Oct 5

ANC10:10 pmAnchorage

15h 09m

2 stops

MDW4:19 pmChicago Midway

$450

Southwest flights from Chicago Midway Airport to Alaska

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

Southwest

Aug 22

MDW2:40 pmChicago Midway

11h 05m

1 stop

ANC10:45 pmAnchorage

Aug 24

ANC10:25 pmAnchorage

8h 25m

1 stop

MDW9:50 amChicago Midway

$637

Southwest

Aug 19

MDW2:10 pmChicago Midway

11h 35m

1 stop

ANC10:45 pmAnchorage

Aug 21

ANC10:25 pmAnchorage

13h 05m

1 stop

MDW2:30 pmChicago Midway

$654

Southwest

Aug 26

MDW10:20 amChicago Midway

13h 55m

2 stops

ANC9:15 pmAnchorage

Sep 3

ANC11:55 pmAnchorage

14h 05m

2 stops

MDW5:00 pmChicago Midway

$657

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

Tue 10/20

10:01 am-8:59 pm

1 stop13h 58m

Anchorage

Tue 10/27

10:09 pm-11:47 am

1 stop10h 38m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Wed 10/21

12:27 pm-8:59 pm

1 stop11h 32m

Anchorage

Mon 10/26

10:09 pm-8:44 am

1 stop7h 35m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 1/26

9:55 am-9:03 pm

1 stop14h 08m

Anchorage

Mon 2/1

9:55 pm-8:49 am

1 stop7h 54m

$443

Quickest round-trip

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Mon 9/28

2:00 pm-9:00 pm

1 stop10h 00m

Anchorage

Mon 10/5

10:10 pm-8:44 am

1 stop7h 34m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Wed 9/16

2:00 pm-9:00 pm

1 stop10h 00m

Anchorage

Wed 9/30

6:00 am-6:19 pm

1 stop9h 19m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 9/15

2:00 pm-9:00 pm

1 stop10h 00m

Anchorage

Mon 9/28

10:10 pm-8:48 am

1 stop7h 38m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Wed 10/21

12:27 pm-8:59 pm

1 stop11h 32m

Anchorage

Wed 10/28

10:09 pm-8:44 am

1 stop7h 35m

$443

ChicagoAnchorage

MDW Chicago Midway - ANC Anchorage

MDWANC

Chicago Midway

Tue 10/20

10:01 am-8:59 pm

1 stop13h 58m

Anchorage

Wed 10/28

10:09 pm-11:47 am

1 stop10h 38m

$443

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

10:06 pm-8:50 am

1 stop7h 44m

$443

ChicagoFairbanks

MDW Chicago Midway - FAI Fairbanks

MDWFAI

Chicago Midway

Fri 1/29

9:55 am-12:15 am

2 stops17h 20m

Fairbanks

Fri 2/5

1:30 am-4:50 pm

2 stops12h 20m

$535

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	$222
Fastest flight time	10h 10m
Direct flights	None

The best one-way flight to Alaska from Chicago Midway Airport in the past 72 hours is $222. The best round-trip flight deal from Chicago Midway Airport to Alaska found on momondo in the last 72 hours is $443.

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

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.