Southwest® flights from Santa Rosa to Chicago (Midway) from $216

Promo Code

Low fares from Santa Rosa to Chicago (Midway)

$

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 04/20/2026

One-way

Basic

From
$216

Low fares from Santa Rosa to Chicago (Midway)

$

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 04/20/2026

One-way

Basic

From
$216
Seen: 2 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 04/20/2026

One-way

Choice

From
$256
Seen: 2 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 04/11/2026

One-way

Basic

From
$273
Seen: 17 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 04/11/2026

One-way

Choice

From
$313
Seen: 17 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 04/20/2026

One-way

Choice Preferred

From
$336
Seen: 2 hrs ago

Santa Rosa (STS)to

Chicago (Midway) (MDW)
Depart: 04/11/2026

One-way

Choice Preferred

From
$393
Seen: 17 hrs ago

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Explore flights from Santa Rosa to Chicago (Midway)

*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:
Chicago Midway International Airport
Distance:
1857 miles

Route Information

46† 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 46 weekly flights from Santa Rosa to Chicago (Midway) on Southwest Airlines.
To find the lowest fares by day and time to fly Santa Rosa to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from Santa Rosa to Chicago (Midway)—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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