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Cheap flights from Alaska to Chicago from $179

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Alaska to Chicago departing on 5/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:15 pm - 8:51 am
ANC
-
MDW
8h 36m
1 stop
Delta Logo
9:31 am - 6:46 pm
MDW
-
ANC
12h 15m
1 stop
$359Delta
Tue, Apr 14 - Mon, Apr 20
Delta Logo
1:44 pm - 8:47 am
ANC
-
MDW
16h 03m
2 stops
Delta Logo
9:31 am - 6:46 pm
MDW
-
ANC
12h 15m
1 stop
$364Delta
Tue, Apr 14 - Mon, Apr 20
Delta Logo
3:45 pm - 8:47 am
ANC
-
MDW
14h 02m
2 stops
Delta Logo
9:27 am - 6:46 pm
MDW
-
ANC
12h 19m
2 stops
$369Delta
Tue, Apr 14 - Mon, Apr 20
Delta Logo
9:55 pm - 8:42 am
ANC
-
MDW
7h 47m
1 stop
Delta Logo
1:59 pm - 12:33 am
MDW
-
ANC
13h 34m
1 stop
$378Delta
Thu, May 7 - Wed, May 13
Delta Logo
5:15 pm - 8:42 am
ANC
-
MDW
12h 27m
2 stops
Delta Logo
1:59 pm - 12:33 am
MDW
-
ANC
13h 34m
1 stop
$383Delta
Thu, May 7 - Wed, May 13
Delta Logo
5:15 pm - 8:42 am
ANC
-
MDW
12h 27m
2 stops
Delta Logo
1:22 pm - 1:35 am
MDW
-
ANC
15h 13m
2 stops
$388Delta
Thu, May 7 - Wed, May 13
Delta Logo
9:55 pm - 1:19 pm
ANC
-
MDW
12h 24m
1 stop
Delta Logo
1:59 pm - 12:33 am
MDW
-
ANC
13h 34m
1 stop
$391Delta
Wed, May 20 - Sat, May 30
Delta Logo
9:55 pm - 1:19 pm
ANC
-
MDW
12h 24m
1 stop
Delta Logo
1:59 pm - 1:35 am
MDW
-
ANC
14h 36m
2 stops
$396Delta
Wed, May 20 - Tue, May 26
Delta Logo
9:55 pm - 8:42 am
ANC
-
MDW
7h 47m
1 stop
Delta Logo
1:59 pm - 12:33 am
MDW
-
ANC
13h 34m
1 stop
$411Delta
Thu, May 7 - Wed, May 13
Delta Logo
9:55 pm - 1:07 pm
ANC
-
MDW
12h 12m
1 stop
Delta Logo
6:45 pm - 12:33 am
MDW
-
ANC
8h 48m
1 stop
$421Delta
Thu, Jul 30 - Sat, Aug 8

Delta flights from Alaska to Chicago Midway Airport

Our best Delta deals on Alaska to Chicago Midway Airport flight tickets
Delta
Apr 14
ANC9:15 pmAnchorage
8h 36m
1 stop
MDW8:51 amChicago Midway
Apr 20
MDW9:31 amChicago Midway
12h 15m
1 stop
ANC6:46 pmAnchorage
$359
Delta
Apr 14
ANC1:44 pmAnchorage
16h 03m
2 stops
MDW8:47 amChicago Midway
Apr 20
MDW9:31 amChicago Midway
12h 15m
1 stop
ANC6:46 pmAnchorage
$364
Delta
Apr 14
ANC3:45 pmAnchorage
14h 02m
2 stops
MDW8:47 amChicago Midway
Apr 20
MDW9:27 amChicago Midway
12h 19m
2 stops
ANC6:46 pmAnchorage
$369

Southwest flights from Alaska to Chicago Midway Airport

Our best Southwest deals on Alaska to Chicago Midway Airport flight tickets
Southwest
Jul 29
ANC12:55 amAnchorage
10h 00m
1 stop
MDW1:55 pmChicago Midway
Aug 6
MDW1:50 pmChicago Midway
12h 55m
2 stops
ANC11:45 pmAnchorage
$728
Southwest
Jul 29
ANC12:55 amAnchorage
11h 20m
2 stops
MDW3:15 pmChicago Midway
Aug 6
MDW1:50 pmChicago Midway
12h 55m
2 stops
ANC11:45 pmAnchorage
$733
Southwest
Jul 28
ANC12:55 amAnchorage
9h 30m
1 stop
MDW1:25 pmChicago Midway
Jul 29
MDW2:55 pmChicago Midway
12h 00m
1 stop
ANC11:55 pmAnchorage
$796

momondo Fare Finder

 
Customize your flight search to find flights from Alaska to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 7, 2026.
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

Tue 4/14

9:15 pm-8:51 am

1 stop8h 36m

Chicago Midway

Mon 4/20

9:31 am-6:46 pm

1 stop12h 15m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/14

1:44 pm-8:47 am

2 stops16h 03m

Chicago Midway

Mon 4/20

9:31 am-6:46 pm

1 stop12h 15m

$364

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/14

3:45 pm-8:47 am

2 stops14h 02m

Chicago Midway

Mon 4/20

9:27 am-6:46 pm

2 stops12h 19m

$369

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

9:55 pm-8:42 am

1 stop7h 47m

Chicago Midway

Wed 5/13

1:59 pm-12:33 am

1 stop13h 34m

$378

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

5:15 pm-8:42 am

2 stops12h 27m

Chicago Midway

Wed 5/13

1:59 pm-12:33 am

1 stop13h 34m

$383

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

5:15 pm-8:42 am

2 stops12h 27m

Chicago Midway

Wed 5/13

1:22 pm-1:35 am

2 stops15h 13m

$388

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 5/20

9:55 pm-1:19 pm

1 stop12h 24m

Chicago Midway

Sat 5/30

1:59 pm-12:33 am

1 stop13h 34m

$391

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 5/20

9:55 pm-1:19 pm

1 stop12h 24m

Chicago Midway

Tue 5/26

1:59 pm-1:35 am

2 stops14h 36m

$396

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

9:55 pm-8:42 am

1 stop7h 47m

Chicago Midway

Wed 5/13

1:59 pm-12:33 am

1 stop13h 34m

$411

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 7/30

9:55 pm-1:07 pm

1 stop12h 12m

Chicago Midway

Sat 8/8

6:45 pm-12:33 am

1 stop8h 48m

$421

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 47m

Direct flights

None
The fastest flight from Alaska to Chicago Midway Airport takes 7h 47m
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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
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.

An easier way to manage your Chicago Midway Airport trip

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