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

On average, it takes 6h 11m to fly from Alaska to Chicago Midway Airport if you fly out of Anchorage (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 Fairbanks and into Chicago O'Hare Intl Airport, then the flight time is around 10h 59m.

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.

$261 Cheap Flights from Alaska to Chicago Midway Airport in 2026/27

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.

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

7h 42m1 stop Minneapolis St Paul

10:34 am - 8:58 pmMDW Chicago Midway-ANC Anchorage

13h 24m1 stop Minneapolis St Paul

$523Delta

Wed, Nov 11 - Mon, Nov 16

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

7h 42m1 stop Minneapolis St Paul

10:34 am - 11:24 pmMDW Chicago Midway-ANC Anchorage

15h 50m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$528Delta

Wed, Nov 11 - Mon, Nov 16

4:04 pm - 8:50 amANC Anchorage-MDW Chicago Midway

13h 46m2 stops Seattle/Tacoma Intl Minneapolis St Paul

10:34 am - 11:24 pmMDW Chicago Midway-ANC Anchorage

15h 50m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$533Delta

Thu, Nov 19 - Mon, Nov 23

4:04 pm - 8:50 amANC Anchorage-MDW Chicago Midway

13h 46m2 stops Seattle/Tacoma Intl Minneapolis St Paul

11:05 am - 5:56 pmMDW Chicago Midway-ANC Anchorage

9h 51m1 stop Minneapolis St Paul

$548Delta

Sun, Nov 22 - Thu, Nov 26

1:40 am - 4:47 pmANC Anchorage-MDW Chicago Midway

12h 07m2 stops Seattle/Tacoma Intl Minneapolis St Paul

10:12 am - 8:41 pmMDW Chicago Midway-ANC Anchorage

13h 29m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$550Delta

Wed, Oct 28 - Thu, Nov 5

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

7h 35m1 stop Minneapolis St Paul

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

13h 47m1 stop Minneapolis St Paul

$551Delta

Thu, Oct 29 - Thu, Nov 5

4:04 pm - 8:50 amANC Anchorage-MDW Chicago Midway

13h 46m2 stops Seattle/Tacoma Intl Minneapolis St Paul

1:31 pm - 11:24 pmMDW Chicago Midway-ANC Anchorage

12h 53m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

$553Delta

Sun, Nov 22 - Wed, Nov 25

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

7h 35m1 stop Minneapolis St Paul

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

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

$556Delta

Thu, Oct 29 - Thu, Nov 5

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

10h 38m1 stop Minneapolis St Paul

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

13h 47m1 stop Minneapolis St Paul

$589Delta

Mon, Oct 26 - Sat, Oct 31

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

10h 38m1 stop Minneapolis St Paul

12:27 pm - 8:41 pmMDW Chicago Midway-ANC Anchorage

11h 14m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$594Delta

Mon, Oct 26 - Sat, Oct 31

Cheap last minute flights

Enter your travel dates to find the best prices.

4:05 pm - 9:32 amANC Anchorage-MDW Chicago Midway

14h 27m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

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

13h 47m1 stop Minneapolis St Paul

$604Delta

Mon, Oct 12 - Thu, Oct 15

4:05 pm - 9:32 amANC Anchorage-MDW Chicago Midway

14h 27m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

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

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

$609Delta

Mon, Oct 12 - Wed, Oct 14

2:24 pm - 9:32 amANC Anchorage-MDW Chicago Midway

16h 08m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

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

13h 47m1 stop Minneapolis St Paul

$686Delta

Mon, Oct 12 - Wed, Oct 14

2:24 pm - 8:44 amANC Anchorage-MDW Chicago Midway

15h 20m2 stops Seattle/Tacoma Intl Minneapolis St Paul

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

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

$731Delta

Tue, Oct 13 - Wed, Oct 14

2:24 pm - 8:44 amANC Anchorage-MDW Chicago Midway

15h 20m2 stops Seattle/Tacoma Intl Minneapolis St Paul

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

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

$734Delta

Mon, Oct 12 - Tue, Oct 13

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

15h 38m1 stop Minneapolis St Paul

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

13h 47m1 stop Minneapolis St Paul

$803Delta

Mon, Oct 12 - Wed, Oct 14

2:24 pm - 8:44 amANC Anchorage-MDW Chicago Midway

15h 20m2 stops Seattle/Tacoma Intl Minneapolis St Paul

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

13h 47m1 stop Minneapolis St Paul

$961Delta

Wed, Oct 14 - Sun, Oct 18

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

7h 35m1 stop Minneapolis St Paul

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

13h 47m1 stop Minneapolis St Paul

$1,413Delta

Wed, Oct 14 - Sun, Oct 18

2:24 pm - 8:44 amANC Anchorage-MDW Chicago Midway

15h 20m2 stops Seattle/Tacoma Intl Minneapolis St Paul

9:29 am - 8:41 pmMDW Chicago Midway-ANC Anchorage

14h 12m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

$1,745Delta

Wed, Oct 14 - Sun, Oct 18

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

10h 38m1 stop Minneapolis St Paul

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

11h 32m1 stop Minneapolis St Paul

$2,056Delta

Mon, Oct 12 - Thu, Oct 15

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Delta flights from Alaska to Chicago Midway Airport

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

Delta

Oct 31

ANC10:17 pmAnchorage

8h 27m

1 stop

MDW9:44 amChicago Midway

Nov 7

MDW6:04 amChicago Midway

15h 15m

1 stop

ANC6:19 pmAnchorage

$459

Delta

Oct 31

ANC10:17 pmAnchorage

8h 27m

1 stop

MDW9:44 amChicago Midway

Nov 7

MDW10:12 amChicago Midway

13h 29m

2 stops

ANC8:41 pmAnchorage

$464

Delta

Nov 11

ANC10:08 pmAnchorage

7h 42m

1 stop

MDW8:50 amChicago Midway

Nov 16

MDW10:34 amChicago Midway

13h 24m

1 stop

ANC8:58 pmAnchorage

$523

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 Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Wed 11/11

10:08 pm-8:50 am

1 stop7h 42m

Chicago Midway

Mon 11/16

10:34 am-8:58 pm

1 stop13h 24m

$523

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Wed 11/11

10:08 pm-8:50 am

1 stop7h 42m

Chicago Midway

Mon 11/16

10:34 am-11:24 pm

2 stops15h 50m

$528

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Thu 11/19

4:04 pm-8:50 am

2 stops13h 46m

Chicago Midway

Mon 11/23

10:34 am-11:24 pm

2 stops15h 50m

$533

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Sun 11/22

4:04 pm-8:50 am

2 stops13h 46m

Chicago Midway

Thu 11/26

11:05 am-5:56 pm

1 stop9h 51m

$548

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Wed 10/28

1:40 am-4:47 pm

2 stops12h 07m

Chicago Midway

Thu 11/5

10:12 am-8:41 pm

2 stops13h 29m

$550

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Thu 10/29

10:09 pm-8:44 am

1 stop7h 35m

Chicago Midway

Thu 11/5

10:12 am-8:59 pm

1 stop13h 47m

$551

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Sun 11/22

4:04 pm-8:50 am

2 stops13h 46m

Chicago Midway

Wed 11/25

1:31 pm-11:24 pm

2 stops12h 53m

$553

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Thu 10/29

10:09 pm-8:44 am

1 stop7h 35m

Chicago Midway

Thu 11/5

9:29 am-8:59 pm

2 stops14h 30m

$556

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Mon 10/26

10:09 pm-11:47 am

1 stop10h 38m

Chicago Midway

Sat 10/31

10:12 am-8:59 pm

1 stop13h 47m

$589

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Mon 10/26

10:09 pm-11:47 am

1 stop10h 38m

Chicago Midway

Sat 10/31

12:27 pm-8:41 pm

2 stops11h 14m

$594

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

Best Price Found	$261
Fastest flight time	7h 42m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Alaska in the past 72 hours is $261. The best round-trip flight deal from Alaska to Chicago Midway Airport found on momondo in the last 72 hours is $523.

The fastest flight from Alaska to Chicago Midway Airport takes 7h 42m

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

Frequently asked questions about flying from Alaska to Chicago Midway Airport

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

Portage

Saint Joseph

Benton Harbor

Lansing

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

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.