Southwest® flights from Chicago-Midway to Santa Rosa from $241

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Low fares from Chicago-Midway to Santa Rosa

$

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 03/12/2027

One-way

Basic

From
$241

Low fares from Chicago-Midway to Santa Rosa

$

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 10/14/2026

One-way

Basic

From
$241
Seen: 10 hrs ago

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 11/06/2026

One-way

Basic

From
$279
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 11/24/2026

One-way

Basic

From
$279
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 10/14/2026

One-way

Choice

From
$291
Seen: 10 hrs ago

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 09/30/2026

One-way

Basic

From
$325
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Santa Rosa (STS)
Depart: 10/01/2026

One-way

Basic

From
$325
Seen: 2 hrs ago

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Explore flights from Chicago-Midway to Santa Rosa

Sep 2026
From$325*
Seen: 21 hrs ago
One Way/Basic
Oct 2026
From$241*
Seen: 10 hrs ago
One Way/Basic
Nov 2026
From$279*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $325
Displaying fares for September-2026
  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

    SEP

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    14

    Mon

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    15

    Tue

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    16

    Wed

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    17

    Thu

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    18

    Fri

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    19

    Sat

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    20

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    21

    Mon

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    22

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  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    23

    Wed

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    24

    Thu

  • MDW–STS, 09/25/2026: From $465
    25

    Fri

  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    26

    Sat

  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    27

    Sun

  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    28

    Mon

  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    29

    Tue

  • MDW–STS, 09/30/2026: From $325
    30

    Wed

  • MDW–STS, 10/01/2026: From $325
    01

    Thu

    OCT

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    02

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    03

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    04

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    05

    Mon

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    06

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    07

    Wed

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    08

    Thu

  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    09

    Fri

  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    10

    Sat

  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    11

    Sun

  • MDW–STS: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

    • Range$325-$465

    *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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