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Cheap flights from Alaska to Chicago from $221

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 9/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
6:00 am - 6:19 pmANC  Anchorage-MDW Chicago Midway
9h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 pm - 8:59 pmMDW  Chicago Midway-ANC Anchorage
11h 32m1 stop Minneapolis St Paul
$443Delta
Thu, Oct 1 - Thu, Oct 8
Delta Logo
6:00 am - 6:19 pmANC  Anchorage-MDW Chicago Midway
9h 19m1 stop Minneapolis St Paul
Delta Logo
9:29 am - 8:59 pmMDW  Chicago Midway-ANC Anchorage
14h 30m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$448Delta
Thu, Oct 1 - Thu, Oct 8
Delta Logo
7:45 pm - 1:47 pmANC  Anchorage-MDW Chicago Midway
15h 02m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:04 am - 8:59 pmMDW  Chicago Midway-ANC Anchorage
17h 55m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul
$453Delta
Sat, Oct 31 - Wed, Nov 4
Delta Logo
6:00 am - 6:19 pmANC  Anchorage-MDW Chicago Midway
9h 19m1 stop Minneapolis St Paul
Delta Logo
10:01 am - 8:59 pmMDW  Chicago Midway-ANC Anchorage
13h 58m1 stop Minneapolis St Paul
$463Delta
Wed, Sep 30 - Wed, Oct 7
Delta Logo
6:00 am - 6:19 pmANC  Anchorage-MDW Chicago Midway
9h 19m1 stop Minneapolis St Paul
Delta Logo
9:29 am - 8:59 pmMDW  Chicago Midway-ANC Anchorage
14h 30m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$468Delta
Wed, Sep 30 - Wed, Oct 7
Delta Logo
10:10 pm - 1:20 pmANC  Anchorage-MDW Chicago Midway
12h 10m1 stop Minneapolis St Paul
Delta Logo
2:00 pm - 9:00 pmMDW  Chicago Midway-ANC Anchorage
10h 00m1 stop Minneapolis St Paul
$473Delta
Fri, Sep 25 - Mon, Sep 28
Delta Logo
2:28 pm - 8:48 amANC  Anchorage-MDW Chicago Midway
15h 20m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
2:00 pm - 9:00 pmMDW  Chicago Midway-ANC Anchorage
10h 00m1 stop Minneapolis St Paul
$478Delta
Fri, Sep 25 - Mon, Sep 28
Delta Logo
10:10 pm - 8:39 amANC  Anchorage-MDW Chicago Midway
7h 29m1 stop Minneapolis St Paul
Delta Logo
1:19 pm - 9:20 pmMDW  Chicago Midway-ANC Anchorage
11h 01m1 stop Detroit Metropolitan Wayne County
$479Delta
Fri, Sep 4 - Mon, Sep 7
Delta Logo
10:10 pm - 12:39 pmANC  Anchorage-MDW Chicago Midway
11h 29m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 9:00 pmMDW  Chicago Midway-ANC Anchorage
14h 31m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$483Delta
Fri, Sep 25 - Mon, Sep 28
Delta Logo
6:00 am - 6:01 pmANC  Anchorage-MDW Chicago Midway
9h 01m1 stop Minneapolis St Paul
Delta Logo
9:29 am - 8:15 pmMDW  Chicago Midway-ANC Anchorage
13h 46m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$484Delta
Fri, Sep 4 - Fri, Sep 11

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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 1
ANC6:00 amAnchorage
9h 19m
1 stop
MDW6:19 pmChicago Midway
Oct 8
MDW12:27 pmChicago Midway
11h 32m
1 stop
ANC8:59 pmAnchorage
$443
Delta
Oct 1
ANC6:00 amAnchorage
9h 19m
1 stop
MDW6:19 pmChicago Midway
Oct 8
MDW9:29 amChicago Midway
14h 30m
2 stops
ANC8:59 pmAnchorage
$448
Delta
Oct 31
ANC7:45 pmAnchorage
15h 02m
2 stops
MDW1:47 pmChicago Midway
Nov 4
MDW6:04 amChicago Midway
17h 55m
2 stops
ANC8:59 pmAnchorage
$453

Southwest flights from Alaska to Chicago Midway Airport

Our best Southwest deals on Alaska to Chicago Midway Airport flight tickets
Southwest
Sep 3
ANC11:55 pmAnchorage
14h 05m
2 stops
MDW5:00 pmChicago Midway
Sep 7
MDW11:10 amChicago Midway
14h 35m
1 stop
ANC10:45 pmAnchorage
$603
Southwest
Sep 3
ANC11:55 pmAnchorage
14h 05m
2 stops
MDW5:00 pmChicago Midway
Sep 7
MDW10:15 amChicago Midway
15h 30m
2 stops
ANC10:45 pmAnchorage
$608
Southwest
Aug 28
ANC10:25 pmAnchorage
9h 10m
1 stop
MDW10:35 amChicago Midway
Sep 1
MDW10:30 amChicago Midway
15h 15m
2 stops
ANC10:45 pmAnchorage
$616

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 August 17, 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

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Thu 10/1

6:00 am-6:19 pm

1 stop9h 19m

Chicago Midway

Thu 10/8

12:27 pm-8:59 pm

1 stop11h 32m

$443

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Thu 10/1

6:00 am-6:19 pm

1 stop9h 19m

Chicago Midway

Thu 10/8

9:29 am-8:59 pm

2 stops14h 30m

$448

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Sat 10/31

7:45 pm-1:47 pm

2 stops15h 02m

Chicago Midway

Wed 11/4

6:04 am-8:59 pm

2 stops17h 55m

$453

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Wed 9/30

6:00 am-6:19 pm

1 stop9h 19m

Chicago Midway

Wed 10/7

10:01 am-8:59 pm

1 stop13h 58m

$463

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Wed 9/30

6:00 am-6:19 pm

1 stop9h 19m

Chicago Midway

Wed 10/7

9:29 am-8:59 pm

2 stops14h 30m

$468

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Fri 9/25

10:10 pm-1:20 pm

1 stop12h 10m

Chicago Midway

Mon 9/28

2:00 pm-9:00 pm

1 stop10h 00m

$473

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Fri 9/25

2:28 pm-8:48 am

2 stops15h 20m

Chicago Midway

Mon 9/28

2:00 pm-9:00 pm

1 stop10h 00m

$478
Quickest round-trip

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Fri 9/4

10:10 pm-8:39 am

1 stop7h 29m

Chicago Midway

Mon 9/7

1:19 pm-9:20 pm

1 stop11h 01m

$479

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Fri 9/25

10:10 pm-12:39 pm

2 stops11h 29m

Chicago Midway

Mon 9/28

9:29 am-9:00 pm

2 stops14h 31m

$483

AnchorageChicago

ANC Anchorage - MDW Chicago Midway

ANCMDW

Anchorage

Fri 9/4

6:00 am-6:01 pm

1 stop9h 01m

Chicago Midway

Fri 9/11

9:29 am-8:15 pm

2 stops13h 46m

$484

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

Best Price Found

$221

Fastest flight time

7h 35m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Alaska in the past 72 hours is $221. The best round-trip flight deal from Alaska to Chicago Midway Airport found on momondo in the last 72 hours is $443.
The fastest flight from Alaska to Chicago Midway Airport takes 7h 35m
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.

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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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