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Southwest® flights from Chicago (Midway) to Anchorage from $269

Promo Code
St. Marteen

Visit Anchorage


Book your flight to Anchorage and explore Alaska's glaciers, wildlife, hiking trails, and unique outdoor adventures.

Flights available to book today. Service starts May 15, 2026.

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Low fares from Chicago (Midway) to Anchorage

$

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 08/21/2026

One-way

Basic

From
$210

Low fares from Chicago (Midway) to Anchorage

$

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 06/02/2026

One-way

Basic

From
$269
Seen: 9 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 07/25/2026

One-way

Basic

From
$306
Seen: 12 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 07/11/2026

One-way

Basic

From
$306
Seen: 7 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 07/03/2026

One-way

Basic

From
$306
Seen: 6 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 06/02/2026

One-way

Choice

From
$319
Seen: 9 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 07/06/2026

One-way

Basic

From
$347
Seen: 9 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

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Explore flights from Chicago (Midway) to Anchorage

May 2026
From$375*
Seen: 13 hrs ago
One Way/Basic
Jun 2026
From$269*
Seen: 9 hrs ago
One Way/Basic
Jul 2026
From$306*
Seen: 6 hrs ago
One Way/Basic
$269
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    • Range$269-$518

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

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