How long does it take to fly to Chicago Midway Airport?

On average, it takes 5h 57m to fly from Alaska to Chicago Midway Airport if you fly out of Fairbanks (the most popular airport in Alaska) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Anchorage and into Chicago O'Hare Intl Airport, then the flight time is around 6h 07m.

When did momondo last update prices for flights from Alaska to Chicago Midway Airport?

Prices for flights from Alaska to Chicago Midway Airport refresh daily.

How old do you have to be to fly from Alaska to Chicago Midway Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Alaska to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The required travel and health documents for your Chicago Midway Airport 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 Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$208 Cheap Flights from Alaska to Chicago Midway Airport in 2026

1 adult

0 bags

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

Find the cheapest flights from Alaska to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:15 pm - 8:46 am

ANC

MDW

8h 31m

1 stop

9:29 am - 6:46 pm

MDW

ANC

12h 17m

1 stop

$417Delta

Tue, Apr 21 - Wed, Apr 29

9:59 pm - 4:12 pm

ANC

MDW

15h 13m

2 stops

1:59 pm - 12:31 am

MDW

ANC

13h 32m

1 stop

$422Delta

Thu, May 7 - Wed, May 13

1:41 pm - 8:47 am

ANC

MDW

16h 06m

2 stops

6:00 am - 6:46 pm

MDW

ANC

15h 46m

2 stops

$427Delta

Fri, Apr 24 - Tue, Apr 28

9:30 pm - 12:42 pm

ANC

MDW

12h 12m

1 stop

9:17 am - 9:16 pm

MDW

ANC

14h 59m

1 stop

$429Delta

Fri, Jun 5 - Fri, Jun 12

6:00 am - 5:56 pm

ANC

MDW

8h 56m

1 stop

6:58 pm - 9:16 pm

MDW

ANC

29h 18m

1 stop

$430Delta

Fri, Jun 5 - Sun, Jun 14

5:20 pm - 9:14 am

ANC

MDW

12h 54m

2 stops

6:55 pm - 1:23 am

MDW

ANC

9h 28m

1 stop

$434Delta

Sun, Jun 7 - Sat, Jun 13

5:15 pm - 8:38 am

ANC

MDW

12h 23m

2 stops

1:00 pm - 12:33 am

MDW

ANC

14h 33m

2 stops

$439Delta

Fri, Sep 18 - Wed, Sep 23

9:15 pm - 1:32 pm

ANC

MDW

13h 17m

1 stop

9:29 am - 6:46 pm

MDW

ANC

12h 17m

1 stop

$450Delta

Tue, Apr 28 - Fri, May 1

9:15 pm - 4:26 pm

ANC

MDW

16h 11m

2 stops

9:29 am - 6:46 pm

MDW

ANC

12h 17m

1 stop

$455Delta

Tue, Apr 28 - Mon, May 4

10:10 pm - 1:09 pm

ANC

MDW

11h 59m

1 stop

9:20 am - 9:20 pm

MDW

ANC

15h 00m

1 stop

$456Delta

Wed, Jul 29 - Sat, Aug 8

Southwest flights from Alaska to Chicago Midway Airport

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

Southwest

May 29

ANC10:25 pmAnchorage

13h 20m

2 stops

MDW2:45 pmChicago Midway

Jun 1

MDW12:35 pmChicago Midway

13h 10m

2 stops

ANC10:45 pmAnchorage

$556

Southwest

Jun 12

ANC11:55 pmAnchorage

16h 35m

2 stops

MDW7:30 pmChicago Midway

Jun 19

MDW11:20 amChicago Midway

12h 55m

2 stops

ANC9:15 pmAnchorage

$626

Southwest

Jun 8

ANC11:55 pmAnchorage

10h 55m

2 stops

MDW1:50 pmChicago Midway

Jun 15

MDW11:20 amChicago Midway

12h 55m

2 stops

ANC9:15 pmAnchorage

$638

Delta flights from Alaska to Chicago Midway Airport

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

Delta

Apr 21

ANC9:15 pmAnchorage

8h 31m

1 stop

MDW8:46 amChicago Midway

Apr 29

MDW9:29 amChicago Midway

12h 17m

1 stop

ANC6:46 pmAnchorage

$417

Delta

May 7

ANC9:59 pmAnchorage

15h 13m

2 stops

MDW4:12 pmChicago Midway

May 13

MDW1:59 pmChicago Midway

13h 32m

1 stop

ANC12:31 amAnchorage

$422

Delta

Apr 24

ANC1:41 pmAnchorage

16h 06m

2 stops

MDW8:47 amChicago Midway

Apr 28

MDW6:00 amChicago Midway

15h 46m

2 stops

ANC6:46 pmAnchorage

$427

momondo Fare Finder

Use the filters below to find and compare flights from Alaska to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/21

9:15 pm-8:46 am

1 stop8h 31m

Chicago Midway

Wed 4/29

9:29 am-6:46 pm

1 stop12h 17m

$417

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

9:59 pm-4:12 pm

2 stops15h 13m

Chicago Midway

Wed 5/13

1:59 pm-12:31 am

1 stop13h 32m

$422

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 4/24

1:41 pm-8:47 am

2 stops16h 06m

Chicago Midway

Tue 4/28

6:00 am-6:46 pm

2 stops15h 46m

$427

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 6/5

9:30 pm-12:42 pm

1 stop12h 12m

Chicago Midway

Fri 6/12

9:17 am-9:16 pm

1 stop14h 59m

$429

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 6/5

6:00 am-5:56 pm

1 stop8h 56m

Chicago Midway

Sun 6/14

6:58 pm-9:16 pm

1 stop29h 18m

$430

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 6/7

5:20 pm-9:14 am

2 stops12h 54m

Chicago Midway

Sat 6/13

6:55 pm-1:23 am

1 stop9h 28m

$434

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 9/18

5:15 pm-8:38 am

2 stops12h 23m

Chicago Midway

Wed 9/23

1:00 pm-12:33 am

2 stops14h 33m

$439

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/28

9:15 pm-1:32 pm

1 stop13h 17m

Chicago Midway

Fri 5/1

9:29 am-6:46 pm

1 stop12h 17m

$450

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/28

9:15 pm-4:26 pm

2 stops16h 11m

Chicago Midway

Mon 5/4

9:29 am-6:46 pm

1 stop12h 17m

$455

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 7/29

10:10 pm-1:09 pm

1 stop11h 59m

Chicago Midway

Sat 8/8

9:20 am-9:20 pm

1 stop15h 00m

$456

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 Alaska to Chicago Midway Airport

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

Airlines

Other information

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

Delta is the most popular carrier operating from Alaska to Chicago Midway

Cheap Alaska to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Alaska to Chicago Midway Airport

Fastest flight time	7h 33m
Direct flights	None

The fastest flight from Alaska to Chicago Midway Airport takes 7h 33m

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

Search flight deals

When did momondo last update prices for flights from Alaska to Chicago Midway Airport?
Prices for flights from Alaska to Chicago Midway Airport refresh daily.
How old do you have to be to fly from Alaska to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Alaska to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport 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 Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Alaska to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Alaska to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Alaska to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Alaska which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Alaska to Chicago?

Once all potential Alaska to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Alaska to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Alaska. 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.