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Cheap flights from Alaska to Chicago from $209

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 6/17. 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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0 bags

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Find the cheapest flights from Alaska to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:08 pm - 1:08 pm
ANC
-
MDW
12h 00m
1 stop
Delta Logo
7:25 pm - 12:59 am
MDW
-
ANC
8h 34m
1 stop
$419Delta
Wed, Aug 12 - Sun, Aug 16
Delta Logo
6:00 am - 6:01 pm
ANC
-
MDW
9h 01m
1 stop
Delta Logo
1:27 pm - 11:24 pm
MDW
-
ANC
12h 57m
2 stops
$424Delta
Wed, Aug 26 - Sun, Aug 30
Delta Logo
9:30 pm - 12:42 pm
ANC
-
MDW
12h 12m
1 stop
Delta Logo
6:00 am - 6:45 pm
MDW
-
ANC
15h 45m
1 stop
$451Delta
Fri, Jun 5 - Sun, Jun 14
Delta Logo
9:30 pm - 12:42 pm
ANC
-
MDW
12h 12m
1 stop
Delta Logo
1:26 pm - 12:55 am
MDW
-
ANC
14h 29m
2 stops
$456Delta
Fri, Jun 5 - Sun, Jun 14
Delta Logo
1:30 am - 6:31 pm
ANC
-
MDW
14h 01m
2 stops
Delta Logo
1:26 pm - 12:55 am
MDW
-
ANC
14h 29m
2 stops
$461Delta
Thu, Jun 11 - Sun, Jun 14
Southwest Logo
11:15 pm - 3:25 pm
ANC
-
MDW
13h 10m
2 stops
Southwest Logo
8:10 am - 11:45 pm
MDW
-
ANC
18h 35m
2 stops
$469Southwest
Wed, Aug 26 - Sun, Aug 30
Delta Logo
10:02 pm - 1:09 pm
ANC
-
MDW
12h 07m
1 stop
Delta Logo
9:17 am - 9:16 pm
MDW
-
ANC
14h 59m
1 stop
$481Delta
Sun, Jun 14 - Fri, Jun 19
Delta Logo
9:30 pm - 12:42 pm
ANC
-
MDW
12h 12m
1 stop
Delta Logo
9:17 am - 9:16 pm
MDW
-
ANC
14h 59m
1 stop
$483Delta
Fri, Jun 5 - Sun, Jun 14
Delta Logo
10:02 pm - 1:09 pm
ANC
-
MDW
12h 07m
1 stop
Delta Logo
1:26 pm - 12:55 am
MDW
-
ANC
14h 29m
2 stops
$486Delta
Mon, Jun 8 - Tue, Jun 16
Delta Logo
9:30 pm - 12:42 pm
ANC
-
MDW
12h 12m
1 stop
Delta Logo
1:26 pm - 12:55 am
MDW
-
ANC
14h 29m
2 stops
$488Delta
Fri, Jun 5 - Sun, Jun 14

Southwest flights from Alaska to Chicago Midway Airport

Our best Southwest deals on Alaska to Chicago Midway Airport flight tickets
Southwest
Aug 26
ANC11:15 pmAnchorage
13h 10m
2 stops
MDW3:25 pmChicago Midway
Aug 30
MDW8:10 amChicago Midway
18h 35m
2 stops
ANC11:45 pmAnchorage
$469
Southwest
Aug 10
ANC12:55 amAnchorage
12h 40m
2 stops
MDW4:35 pmChicago Midway
Aug 17
MDW4:00 pmChicago Midway
10h 45m
1 stop
ANC11:45 pmAnchorage
$526
Southwest
Jun 23
ANC11:55 pmAnchorage
10h 55m
2 stops
MDW1:50 pmChicago Midway
Jun 30
MDW2:55 pmChicago Midway
10h 50m
1 stop
ANC10:45 pmAnchorage
$539

Delta flights from Alaska to Chicago Midway Airport

Our best Delta deals on Alaska to Chicago Midway Airport flight tickets
Delta
Aug 12
ANC10:08 pmAnchorage
12h 00m
1 stop
MDW1:08 pmChicago Midway
Aug 17
MDW7:25 pmChicago Midway
8h 34m
1 stop
ANC12:59 amAnchorage
$419
Delta
Aug 26
ANC6:00 amAnchorage
9h 01m
1 stop
MDW6:01 pmChicago Midway
Aug 30
MDW1:27 pmChicago Midway
12h 57m
2 stops
ANC11:24 pmAnchorage
$424
Delta
Jun 5
ANC9:30 pmAnchorage
12h 12m
1 stop
MDW12:42 pmChicago Midway
Jun 14
MDW6:00 amChicago Midway
15h 45m
1 stop
ANC6:45 pmAnchorage
$451

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 May 10, 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

Wed 8/12

10:08 pm-1:08 pm

1 stop12h 00m

Chicago Midway

Sun 8/16

7:25 pm-12:59 am

1 stop8h 34m

$419

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 8/26

6:00 am-6:01 pm

1 stop9h 01m

Chicago Midway

Sun 8/30

1:27 pm-11:24 pm

2 stops12h 57m

$424

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 6/5

9:30 pm-12:42 pm

1 stop12h 12m

Chicago Midway

Sun 6/14

6:00 am-6:45 pm

1 stop15h 45m

$451

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 6/5

9:30 pm-12:42 pm

1 stop12h 12m

Chicago Midway

Sun 6/14

1:26 pm-12:55 am

2 stops14h 29m

$456

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 6/11

1:30 am-6:31 pm

2 stops14h 01m

Chicago Midway

Sun 6/14

1:26 pm-12:55 am

2 stops14h 29m

$461

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 8/26

11:15 pm-3:25 pm

2 stops13h 10m

Chicago Midway

Sun 8/30

8:10 am-11:45 pm

2 stops18h 35m

$469

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 6/14

10:02 pm-1:09 pm

1 stop12h 07m

Chicago Midway

Fri 6/19

9:17 am-9:16 pm

1 stop14h 59m

$481

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 6/5

9:30 pm-12:42 pm

1 stop12h 12m

Chicago Midway

Sun 6/14

9:17 am-9:16 pm

1 stop14h 59m

$483

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 6/8

10:02 pm-1:09 pm

1 stop12h 07m

Chicago Midway

Tue 6/16

1:26 pm-12:55 am

2 stops14h 29m

$486

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 6/5

9:30 pm-12:42 pm

1 stop12h 12m

Chicago Midway

Sun 6/14

1:26 pm-12:55 am

2 stops14h 29m

$488

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 27m

Direct flights

None
The fastest flight from Alaska to Chicago Midway Airport takes 7h 27m
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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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.

An easier way to manage your Chicago Midway Airport trip

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