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Cheap flights from Alaska to Chicago from $201

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 8/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Alaska to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:10 pm - 8:48 am
ANC
-
MDW
7h 38m
1 stop
Delta Logo
12:28 pm - 8:55 pm
MDW
-
ANC
11h 27m
1 stop
$413Delta
Fri, Sep 25 - Thu, Oct 15
Delta Logo
6:00 am - 6:19 pm
ANC
-
MDW
9h 19m
1 stop
Delta Logo
1:19 pm - 12:45 am
MDW
-
ANC
14h 26m
2 stops
$418Delta
Fri, Oct 2 - Mon, Oct 5
Delta Logo
5:15 pm - 8:49 am
ANC
-
MDW
12h 34m
2 stops
Delta Logo
12:30 pm - 10:36 pm
MDW
-
ANC
13h 06m
2 stops
$423Delta
Fri, Nov 13 - Sun, Nov 22
Delta Logo
10:10 pm - 3:57 pm
ANC
-
MDW
14h 47m
1 stop
Delta Logo
9:59 am - 5:14 pm
MDW
-
ANC
10h 15m
1 stop
$451Delta
Fri, Sep 4 - Sat, Sep 12
Delta Logo
8:10 pm - 4:15 pm
ANC
-
MDW
17h 05m
1 stop
Delta Logo
9:54 am - 11:20 pm
MDW
-
ANC
16h 26m
2 stops
$456Delta
Mon, Jul 13 - Tue, Jul 28
Delta Logo
10:10 pm - 8:48 am
ANC
-
MDW
7h 38m
1 stop
Delta Logo
9:59 am - 8:55 pm
MDW
-
ANC
13h 56m
1 stop
$458Delta
Mon, Sep 28 - Mon, Oct 12
Delta Logo
10:10 pm - 6:25 pm
ANC
-
MDW
17h 15m
2 stops
Delta Logo
9:54 am - 11:20 pm
MDW
-
ANC
16h 26m
2 stops
$461Delta
Mon, Jul 13 - Tue, Jul 28
Delta Logo
6:00 am - 10:45 pm
ANC
-
MDW
13h 45m
2 stops
Delta Logo
9:59 am - 8:55 pm
MDW
-
ANC
13h 56m
1 stop
$463Delta
Mon, Sep 28 - Mon, Oct 12
Delta Logo
12:54 pm - 8:39 am
ANC
-
MDW
16h 45m
1 stop
Delta Logo
9:24 am - 9:20 pm
MDW
-
ANC
14h 56m
1 stop
$468Delta
Fri, Aug 7 - Sun, Aug 9
Southwest Logo
11:55 pm - 5:00 pm
ANC
-
MDW
14h 05m
2 stops
Southwest Logo
10:30 am - 10:45 pm
MDW
-
ANC
15h 15m
2 stops
$470Southwest
Wed, Aug 12 - Wed, Aug 19

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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
Sep 25
ANC10:10 pmAnchorage
7h 38m
1 stop
MDW8:48 amChicago Midway
Oct 11
MDW12:28 pmChicago Midway
11h 27m
1 stop
ANC8:55 pmAnchorage
$413
Delta
Nov 13
ANC9:55 pmAnchorage
7h 54m
1 stop
MDW8:49 amChicago Midway
Nov 22
MDW12:30 pmChicago Midway
13h 06m
2 stops
ANC10:36 pmAnchorage
$418
Delta
Nov 13
ANC5:15 pmAnchorage
12h 34m
2 stops
MDW8:49 amChicago Midway
Nov 22
MDW12:30 pmChicago Midway
13h 06m
2 stops
ANC10:36 pmAnchorage
$423

Southwest flights from Alaska to Chicago Midway Airport

Our best Southwest deals on Alaska to Chicago Midway Airport flight tickets
Southwest
Aug 12
ANC11:55 pmAnchorage
14h 05m
2 stops
MDW5:00 pmChicago Midway
Aug 19
MDW10:30 amChicago Midway
15h 15m
2 stops
ANC10:45 pmAnchorage
$470
Southwest
Aug 12
ANC11:55 pmAnchorage
14h 05m
2 stops
MDW5:00 pmChicago Midway
Aug 19
MDW2:10 pmChicago Midway
11h 35m
1 stop
ANC10:45 pmAnchorage
$480
Southwest
Aug 20
ANC11:55 pmAnchorage
14h 05m
2 stops
MDW5:00 pmChicago Midway
Aug 26
MDW10:30 amChicago Midway
15h 15m
2 stops
ANC10:45 pmAnchorage
$538

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 July 2, 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

Cheapest round-trip
Quickest round-trip

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 9/25

10:10 pm-8:48 am

1 stop7h 38m

Chicago Midway

Thu 10/15

12:28 pm-8:55 pm

1 stop11h 27m

$413

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 10/2

6:00 am-6:19 pm

1 stop9h 19m

Chicago Midway

Mon 10/5

1:19 pm-12:45 am

2 stops14h 26m

$418

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 11/13

5:15 pm-8:49 am

2 stops12h 34m

Chicago Midway

Sun 11/22

12:30 pm-10:36 pm

2 stops13h 06m

$423

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 9/4

10:10 pm-3:57 pm

1 stop14h 47m

Chicago Midway

Sat 9/12

9:59 am-5:14 pm

1 stop10h 15m

$451

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 7/13

8:10 pm-4:15 pm

1 stop17h 05m

Chicago Midway

Tue 7/28

9:54 am-11:20 pm

2 stops16h 26m

$456

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 9/28

10:10 pm-8:48 am

1 stop7h 38m

Chicago Midway

Mon 10/12

9:59 am-8:55 pm

1 stop13h 56m

$458

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 7/13

10:10 pm-6:25 pm

2 stops17h 15m

Chicago Midway

Tue 7/28

9:54 am-11:20 pm

2 stops16h 26m

$461

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 9/28

6:00 am-10:45 pm

2 stops13h 45m

Chicago Midway

Mon 10/12

9:59 am-8:55 pm

1 stop13h 56m

$463

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 8/7

12:54 pm-8:39 am

1 stop16h 45m

Chicago Midway

Sun 8/9

9:24 am-9:20 pm

1 stop14h 56m

$468

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 8/12

11:55 pm-5:00 pm

2 stops14h 05m

Chicago Midway

Wed 8/19

10:30 am-10:45 pm

2 stops15h 15m

$470

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 and Southwest are the most popular carriers 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 39m

Direct flights

None
The fastest flight from Alaska to Chicago Midway Airport takes 7h 39m
There are no direct flights from Alaska to Chicago Midway Airport. There are no popular flight routes from Alaska to Chicago Midway Airport.
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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.

Traveling to a place near Chicago?

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

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