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CA $283 Cheap Flights from Chicago (ORD) to Santa Rosa (STS)

View CA $283 flight on Sat, Aug 8, 2026Opens in a new window

Popular airlines from Chicago O'Hare International Airport (ORD) to Santa Rosa, CA (STS-Sonoma County)

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Cheap flights from Chicago (ORD) to Santa Rosa (STS)

Prices were available within the past 7 days and start at CA $283 for one-way flights and CA $655 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Aug 8 - Sun, Aug 9
ORD
Chicago
STS
Santa Rosa
CA $655 Roundtrip, found 5 days ago
CA $655
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 8 from Chicago to Santa Rosa, returning Sun, Aug 9, priced at CA $655 found 5 days ago
Alaska Airlines
Sat, Aug 8 - Sun, Aug 9
ORD
Chicago
STS
Santa Rosa
CA $685 Roundtrip, found 5 days ago
CA $685
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sat, Aug 8 from Chicago to Santa Rosa, returning Sun, Aug 9, priced at CA $685 found 5 days ago
Alaska Airlines
Sat, Aug 8 - Sun, Aug 9
ORD
Chicago
STS
Santa Rosa
CA $721 Roundtrip, found 5 days ago
CA $721
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sat, Aug 8 from Chicago to Santa Rosa, returning Sun, Aug 9, priced at CA $721 found 5 days ago
Alaska Airlines
Wed, Aug 12 - Sun, Aug 16
ORD
Chicago
STS
Santa Rosa
CA $734 Roundtrip, found 2 days ago
CA $734
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Aug 12 from Chicago to Santa Rosa, returning Sun, Aug 16, priced at CA $734 found 2 days ago
Alaska Airlines
Wed, Aug 12 - Sun, Aug 16
ORD
Chicago
STS
Santa Rosa
CA $778 Roundtrip, found 2 days ago
CA $778
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Aug 12 from Chicago to Santa Rosa, returning Sun, Aug 16, priced at CA $778 found 2 days ago
American Airlines
Sat, Aug 8 - Sun, Aug 9
ORD
Chicago
STS
Santa Rosa
CA $779 Roundtrip, found 5 days ago
CA $779
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 8 from Chicago to Santa Rosa, returning Sun, Aug 9, priced at CA $779 found 5 days ago
Alaska Airlines
Sat, Aug 8 - Sun, Aug 9
ORD
Chicago
STS
Santa Rosa
CA $792 Roundtrip, found 5 days ago
CA $792
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sat, Aug 8 from Chicago to Santa Rosa, returning Sun, Aug 9, priced at CA $792 found 5 days ago
Alaska Airlines
Thu, Aug 13 - Sun, Aug 16
ORD
Chicago
STS
Santa Rosa
CA $804 Roundtrip, found 2 days ago
CA $804
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Thu, Aug 13 from Chicago to Santa Rosa, returning Sun, Aug 16, priced at CA $804 found 2 days ago
Alaska Airlines
Wed, Aug 12 - Sun, Aug 16
ORD
Chicago
STS
Santa Rosa
CA $812 Roundtrip, found 2 days ago
CA $812
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Aug 12 from Chicago to Santa Rosa, returning Sun, Aug 16, priced at CA $812 found 2 days ago
American Airlines
Sat, Aug 8 - Sun, Aug 9
ORD
Chicago
STS
Santa Rosa
CA $834 Roundtrip, found 5 days ago
CA $834
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 8 from Chicago to Santa Rosa, returning Sun, Aug 9, priced at CA $834 found 5 days ago

Frequently asked questions

How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
There are approximately 17 connecting flights per day from Chicago, IL (ORD-O'Hare Intl.) (ORD) to Santa Rosa, CA (STS-Sonoma County) (STS). Some common connection points include Seattle - Tacoma Intl. (SEA), Portland Intl. (PDX), and San Diego Intl. (SAN).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) typically departs at approximately 12:00 AM local time, operated by American Airlines. This is a seasonal service active in December. An early departure like this can help maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
You'll typically find the most flights from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) on a Monday, with around 21 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Alaska Airlines, American Airlines, and Southwest Airlines. Flight schedules are consistent throughout the week.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
The most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) are in the morning, from 6am to 9am. About 37% of passengers prefer this time. Alaska Airlines and American Airlines offer flights during this window. This timing works well because it allows you to get an early start on your travel day and arrive at your destination with plenty of time left.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
Flights from ORD to STS with one stop typically take around 9 hours 30 minutes, covering approximately 1,843 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
Select the "Business class" and "First class" filters when looking for ORD to STS flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Santa Rosa from O'Hare Intl. (ORD)?
If you're planning to travel to Santa Rosa from O'Hare Intl. (ORD), you can fly into Sonoma County (STS) Some flights may connect through major hubs like Seattle - Tacoma Intl. (SEA), Hartsfield-Jackson Atlanta Intl. (ATL), Minneapolis - St. Paul Intl. (MSP) before reaching Santa Rosa. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Santa Rosa, CA (STS-Sonoma County) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Sonoma County
Roundtrip price
CA $654
Distance
2949 km

Book with confidence

Chicago to Windsor Flights

The easy way to book your flights from Chicago to Santa Rosa 

With Expedia, it’s simple to find and book flights to Santa Rosa from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Sonoma County, too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Santa Rosa today, tomorrow, or this week.  

 

Save dollars with cheap flights from O'Hare Intl., ORD to Sonoma County, STS 

Sort your search results by price to find great deals on your flight from Chicago to Santa Rosa—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Santa Rosa from Chicago currently is just CA $655 rising to CA $834.  

Here are more money-saving tips: 

  • Fly in August when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Santa Rosa  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Santa Rosa from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Santa Rosa with Expedia today.

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