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

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

$

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

$

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 06/06/2026

One-way

Basic

From
$249
Seen: 12 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 06/06/2026

One-way

Choice

From
$294
Seen: 12 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 06/07/2026

One-way

Basic

From
$355
Seen: 12 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 06/06/2026

One-way

Choice Preferred

From
$374
Seen: 12 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 06/07/2026

One-way

Choice

From
$387
Seen: 12 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 06/06/2026

One-way

Choice Extra

From
$434
Seen: 12 hrs ago

Looking for more low-fare flights?

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.

Find low fares

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

May 2026
From$525*
Seen: 7 hrs ago
One Way/Basic
Jun 2026
From$249*
Seen: 12 hrs ago
One Way/Basic
Jul 2026
No result for this month.
$525
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    • Range$525

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

    Route Information

    8† 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 8 weekly flights from Chicago (O'Hare) to Santa Rosa on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (O'Hare) to Santa Rosa with Southwest, check out our Low Fare Calendar.
    You can rent a car at Charles M. Schulz–Sonoma County Airport book yours with your flight.
    Yes! Flights from Chicago (O'Hare) to Santa Rosa—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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