Southwest® flights from Anchorage to Chicago (O'Hare)

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Low fares from Anchorage to Chicago (O'Hare)

$

Anchorage (ANC)to

Chicago (O'Hare) (ORD)
Depart: 08/16/2026

One-way

Basic

From
$184

Low fares from Anchorage to Chicago (O'Hare)

$

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/21/2026

One-way

Basic

From
$184
Seen: 18 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/21/2026

One-way

Choice

From
$224
Seen: 18 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/21/2026

One-way

Choice Preferred

From
$314
Seen: 18 hrs ago

Anchorage (ANC)to

Chicago (Midway) (MDW)
Depart: 05/21/2026

One-way

Choice Extra

From
$384
Seen: 18 hrs ago

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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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