Southwest® flights from Santa Rosa to Chicago (O'Hare) from $218

Promo Code

Low fares from Santa Rosa to Chicago (O'Hare)

$

Santa Rosa (STS)to

Chicago (O'Hare) (ORD)
Depart: 05/19/2026

One-way

Basic

From
$218

Low fares from Santa Rosa to Chicago (O'Hare)

$

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 05/02/2026

One-way

Basic

From
$215
Seen: 3 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 04/23/2026

One-way

Basic

From
$244
Seen: 3 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 06/19/2026

One-way

Basic

From
$260
Seen: 1 hour ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 05/02/2026

One-way

Choice

From
$260
Seen: 3 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 05/29/2026

One-way

Basic

From
$265
Seen: 22 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 05/08/2026

One-way

Basic

From
$265
Seen: 11 hrs ago

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Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

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Explore flights from Santa Rosa to Chicago (O'Hare)

Apr 2026
From$244*
Seen: 3 hrs ago
One Way/Basic
May 2026
From$215*
Seen: 3 hrs ago
One Way/Basic
Jun 2026
From$260*
Seen: 1 hour ago
One Way/Basic
$244
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    • Range$244-$390

    *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.

    Flight Details

    Departing from:
    Charles M. Schulz–Sonoma County Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    1848 miles

    Route Information

    12† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 12 weekly flights from Santa Rosa to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Santa Rosa to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Santa Rosa to Chicago (O'Hare)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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