Southwest® flights from Chicago (Midway) to Anchorage from $215

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: 05/28/2026

One-way

Basic

From
$215

Low fares from Chicago (Midway) to Anchorage

$

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 05/28/2026

One-way

Basic

From
$215
Seen: 51 minutes ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 05/18/2026

One-way

Basic

From
$255
Seen: 1 hour ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 05/28/2026

One-way

Choice

From
$265
Seen: 51 minutes ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 05/30/2026

One-way

Basic

From
$272
Seen: 3 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 06/06/2026

One-way

Basic

From
$272
Seen: 1 hour ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 06/23/2026

One-way

Basic

From
$272
Seen: 34 minutes ago

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Explore flights from Chicago (Midway) to Anchorage

Try alternate month or interact with individual days below in order to find offers.
Apr 2026
No result for this month.
May 2026
From$215*
Seen: 51 minutes ago
One Way/Basic
Jun 2026
From$272*
Seen: 1 hour ago
One Way/Basic
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    • *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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