$240 Cheap Flights from Chicago (MDW) to Santa Rosa (STS)

View $240 flight on Sat, May 16, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Santa Rosa, CA (STS-Sonoma County)

Cheap Flights from Chicago to Santa Rosa (MDW-STS)

Prices were available within the past 7 days and start at $240 for one-way flights and $479 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$479 Roundtrip, found 4 days ago
$479
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $479 found 4 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$484 Roundtrip, found 4 days ago
$484
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $484 found 4 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$489 Roundtrip, found 4 days ago
$489
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $489 found 4 days ago
Southwest Airlines
Fri, Apr 17 - Sun, Apr 19
MDW
Chicago
STS
Santa Rosa
$499 Roundtrip, found 5 days ago
$499
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Apr 17 from Chicago to Santa Rosa, returning Sun, Apr 19, priced at $499 found 5 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$559 Roundtrip, found 4 days ago
$559
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $559 found 4 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$564 Roundtrip, found 4 days ago
$564
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $564 found 4 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$569 Roundtrip, found 4 days ago
$569
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $569 found 4 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$579 Roundtrip, found 4 days ago
$579
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $579 found 4 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$584 Roundtrip, found 4 days ago
$584
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $584 found 4 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
MDW
Chicago
STS
Santa Rosa
$589 Roundtrip, found 4 days ago
$589
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Chicago to Santa Rosa, returning Mon, Apr 13, priced at $589 found 4 days ago

Alternative airports near Santa Rosa

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Sonoma County STS. Cheapest and Closest option available. Average driving time to city center is 10 minutes. Flights from $890
STS
Sonoma County
CheapestClosest
Average driving time to city center10 min
Flights from $890

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Sonoma County Airport (STS) cost?
Snag a cheap one-way flight from $240 or cheap return flight from $479 from Midway Intl. Airport (MDW) to Sonoma County Airport (STS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Sonoma County Airport (STS)?
April is the least expensive month to fly from MDW to STS. Planning your trip for the off-season is often the key to landing a great deal.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Sonoma County Airport (STS)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to STS flight.
How many flights per day from Midway Intl. Airport (MDW) to Sonoma County Airport (STS)?
Nonstop flights from Midway Intl. Airport (MDW) to Sonoma County Airport (STS) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to STS?
Generally you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can change based on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Sonoma County Airport (STS)?
To land at Sonoma County Airport (STS) on schedule, opt for a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Santa Rosa from Midway Intl. Airport (MDW)?
You can arrive at San Francisco Intl. Airport (SFO) or Oakland Intl. Airport (OAK) when you travel to Santa Rosa on a direct flight from Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Sonoma County Airport (STS) last-minute?
Waiting until just before your departure to book a ticket from MDW to STS often results in higher prices. While you may come across some last-minute offers, they aren't always guaranteed. Allow some flexibility in your schedule to boost your chances of landing a bargain.
Is it cheaper to book a MDW to STS flight and hotel package?
Opting for a MDW to STS flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Choose from our wide range of accommodations and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Sonoma County Airport (STS)?
If you reserved your MDW to STS flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Sonoma County
Roundtrip price
$478
Distance
1852 mi

Book with confidence

Chicago to Santa Rosa Flights

The cheapest times to fly from Chicago to Santa Rosa

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Santa Rosa are during the month of April. You can find some of the cheapest flights from Chicago to Santa Rosa with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Santa Rosa

Sunday is one of the best days to book for cheap flights from Chicago to Santa Rosa: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Santa Rosa

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Santa Rosa in 2025. You can also book with separate airlines for your outbound and return journeys, from $240 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Santa Rosa flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Santa Rosa airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Santa Rosa Flights

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*Available to One Key members.