Southwest® flights from Anchorage to Chicago (Midway) from $254

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Low fares from Anchorage to Chicago (Midway)

$

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 07/15/2026

One-way

Basic

From
$254
Seen: 4 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 06/15/2026

One-way

Basic

From
$274
Seen: 4 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 06/14/2026

One-way

Basic

From
$277
Seen: 4 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 06/16/2026

One-way

Basic

From
$299
Seen: 4 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 07/15/2026

One-way

Choice

From
$304
Seen: 4 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 07/16/2026

One-way

Basic

From
$321
Seen: 4 hrs ago

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Explore flights from Anchorage to Chicago (Midway)

Jun 2026
From$274*
Seen: 4 hrs ago
One Way/Basic
Jul 2026
From$254*
Seen: 4 hrs ago
One Way/Basic
Aug 2026
No result for this month.
cmp-daily-histogram-bars-legend-min-price-aria-label $274
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    • Range$274-$367

    *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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