Southwest® flights from Chicago (Midway) to Santa Rosa from $215

Promo Code
St. Marteen

Visit Santa Rosa


Discover the best of Sonoma County (Santa Rosa) and unwind with world-class wines and stunning views of the redwoods.

Flights available to book today. Service starts April 7, 2026.

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Low fares from Chicago (Midway) to Santa Rosa

$

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 04/14/2026

One-way

Basic

From
$215

Low fares from Chicago (Midway) to Santa Rosa

$

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 04/14/2026

One-way

Basic

From
$215
Seen: 2 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 05/09/2026

One-way

Basic

From
$215
Seen: 35 minutes ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 04/03/2026

One-way

Basic

From
$239
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 06/10/2026

One-way

Basic

From
$239
Seen: 6 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 04/05/2026

One-way

Basic

From
$239
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

Santa Rosa (STS)
Depart: 04/02/2026

One-way

Basic

From
$239
Seen: 21 hrs ago

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Explore flights from Chicago (Midway) to Santa Rosa

Try alternate month or interact with individual days below in order to find offers.
Mar 2026
No result for this month.
Apr 2026
From$215*
Seen: 2 hrs ago
One Way/Basic
May 2026
From$215*
Seen: 35 minutes ago
One Way/Basic
$215
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    • Range$215-$239

    *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:
    Chicago Midway International Airport
    Arriving at:
    Charles M. Schulz–Sonoma County Airport
    Distance:
    1857 miles

    Route Information

    39† 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 39 weekly flights from Chicago (Midway) to Santa Rosa on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) 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 (Midway) 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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