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

On average, it takes 6h 02m 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 6h 04m.

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.

$178 Cheap Flights from Alaska to Chicago Midway Airport in 2025/26

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Cheap round-trip flights

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9:45 pm - 9:19 amANC-MDW

8h 34m1 stop

5:59 pm - 1:22 amMDW-ANC

10h 23m1 stop

$358Delta

Find Deal

vie., dic. 12 - dom., dic. 28

9:45 pm - 3:44 pmANC-MDW

14h 59m2 stops

5:59 pm - 1:22 amMDW-ANC

10h 23m1 stop

$363Delta

Find Deal

vie., dic. 12 - dom., dic. 28

1:30 am - 6:18 pmFAI-MDW

13h 48m2 stops

9:59 am - 12:18 amMDW-FAI

17h 19m2 stops

$402Delta

Find Deal

jue., dic. 4 - mar., dic. 9

5:37 pm - 9:54 amANC-MDW

13h 17m2 stops

1:14 pm - 10:42 pmMDW-ANC

12h 28m2 stops

$433Delta

Find Deal

jue., dic. 4 - jue., dic. 11

9:45 pm - 1:10 pmANC-MDW

12h 25m1 stop

5:59 pm - 1:22 amMDW-ANC

10h 23m1 stop

$438Delta

Find Deal

vie., dic. 12 - dom., dic. 28

1:30 am - 6:34 pmANC-MDW

14h 04m2 stops

6:45 pm - 12:50 amMDW-ANC

9h 05m1 stop

$443Delta

Find Deal

mar., mar. 24 - dom., mar. 29

9:55 pm - 6:08 pmANC-MDW

17h 13m1 stop

6:45 pm - 12:50 amMDW-ANC

9h 05m1 stop

$468Delta

Find Deal

mié., mar. 25 - dom., mar. 29

12:30 am - 6:00 pmANC-MDW

14h 30m2 stops

5:59 pm - 1:22 amMDW-ANC

10h 23m1 stop

$473Delta

Find Deal

jue., dic. 11 - dom., dic. 28

1:30 am - 8:54 amANC-MDW

28h 24m2 stops

1:00 pm - 12:28 amMDW-ANC

14h 28m2 stops

$478Delta

Find Deal

mar., mar. 24 - dom., mar. 29

1:30 am - 6:34 pmANC-MDW

14h 04m2 stops

1:00 pm - 12:28 amMDW-ANC

14h 28m2 stops

$520Delta

Find Deal

mar., mar. 24 - dom., mar. 29

Delta flights from Alaska to Chicago Midway Airport

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

Delta

Dec 12

ANC9:45 pmAnchorage

8h 34m

1 stop

MDW9:19 amChicago Midway

Dec 28

MDW5:59 pmChicago Midway

10h 23m

1 stop

ANC1:22 amAnchorage

$358

Find similar

Delta

Dec 12

ANC9:45 pmAnchorage

14h 59m

2 stops

MDW3:44 pmChicago Midway

Dec 28

MDW5:59 pmChicago Midway

10h 23m

1 stop

ANC1:22 amAnchorage

$363

Find similar

Delta

Dec 4

FAI1:30 amFairbanks

13h 48m

2 stops

MDW6:18 pmChicago Midway

Dec 9

MDW9:59 amChicago Midway

17h 19m

2 stops

FAI12:18 amFairbanks

$402

Find similar

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

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

vie. 12/12

9:45 pm-9:19 am

1 stop8h 34m

Chicago Midway

dom. 12/28

5:59 pm-1:22 am

1 stop10h 23m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

vie. 12/12

9:45 pm-3:44 pm

2 stops14h 59m

Chicago Midway

dom. 12/28

5:59 pm-1:22 am

1 stop10h 23m

$363

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

jue. 12/4

1:30 am-6:18 pm

2 stops13h 48m

Chicago Midway

mar. 12/9

9:59 am-12:18 am

2 stops17h 19m

$402

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

jue. 12/4

5:37 pm-9:54 am

2 stops13h 17m

Chicago Midway

jue. 12/11

1:14 pm-10:42 pm

2 stops12h 28m

$433

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

vie. 12/12

9:45 pm-1:10 pm

1 stop12h 25m

Chicago Midway

dom. 12/28

5:59 pm-1:22 am

1 stop10h 23m

$438

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

mar. 3/24

1:30 am-6:34 pm

2 stops14h 04m

Chicago Midway

dom. 3/29

6:45 pm-12:50 am

1 stop9h 05m

$443

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

mié. 3/25

9:55 pm-6:08 pm

1 stop17h 13m

Chicago Midway

dom. 3/29

6:45 pm-12:50 am

1 stop9h 05m

$468

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

jue. 12/11

12:30 am-6:00 pm

2 stops14h 30m

Chicago Midway

dom. 12/28

5:59 pm-1:22 am

1 stop10h 23m

$473

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

mar. 3/24

1:30 am-8:54 am

2 stops28h 24m

Chicago Midway

dom. 3/29

1:00 pm-12:28 am

2 stops14h 28m

$478

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

mar. 3/24

1:30 am-6:34 pm

2 stops14h 04m

Chicago Midway

dom. 3/29

1:00 pm-12:28 am

2 stops14h 28m

$520

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

Direct flights	None

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.

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Munster

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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.