Southwest® flights from Chicago (Midway) to Anchorage from $302

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Low fares from Chicago (Midway) to Anchorage

$

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 08/06/2026

One-way

Basic

From
$302
Seen: 1 hour ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 05/28/2026

One-way

Basic

From
$330
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 06/24/2026

One-way

Basic

From
$333
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 08/06/2026

One-way

Choice

From
$352
Seen: 1 hour ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 05/23/2026

One-way

Basic

From
$362
Seen: 9 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 08/27/2026

One-way

Basic

From
$373
Seen: 8 hrs ago

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Explore flights from Chicago (Midway) to Anchorage

May 2026
From$330*
Seen: 13 hrs ago
One Way/Basic
Jun 2026
From$333*
Seen: 11 hrs ago
One Way/Basic
Jul 2026
From$377*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $330
cmp-daily-histogram-bars-legend-max-price-aria-label $548
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    • Range$330-$548

    *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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