Southwest® flights from Anchorage to Chicago (Midway) from $214

Promo Code

Low fares from Anchorage to Chicago (Midway)

$

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/25/2026

One-way

Basic

From
$214

Low fares from Anchorage to Chicago (Midway)

$

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/25/2026

One-way

Basic

From
$214
Seen: 12 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/25/2026

One-way

Choice

From
$254
Seen: 12 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/13/2026

One-way

Basic

From
$268
Seen: 23 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 06/05/2026

One-way

Basic

From
$279
Seen: 14 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 06/06/2026

One-way

Basic

From
$284
Seen: 14 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/13/2026

One-way

Choice

From
$308
Seen: 23 hrs ago

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Mar 2026
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Apr 2026
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May 2026
From$214*
Seen: 12 hrs 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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