Southwest® flights from Chicago-Midway to Santa Rosa from $560

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Low fares from Chicago-Midway to Santa Rosa

$

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 03/29/2027

One-way

Basic

From
$288

Low fares from Chicago-Midway to Santa Rosa

$

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 11/13/2026

One-way

Choice

From
$560
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 11/13/2026

One-way

Choice Preferred

From
$640
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 11/13/2026

One-way

Choice Extra

From
$700
Seen: 8 hrs ago

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Explore flights from Chicago-Midway to Santa Rosa

Nov 2026
From$560*
Seen: 8 hrs ago
One Way/Basic
Dec 2026
No result for this month.
Jan 2027
No result for this month.
cmp-daily-histogram-bars-legend-min-price-aria-label $560
Displaying fares for November-2026
  • MDW–STS, 11/13/2026: From $560
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    • Range$560

    *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

    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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