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$204+ Cheap flights from Chicago (CHI) to Santa Rosa (STS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
1 adult, Economy
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Cheap flight deals from Chicago to Santa Rosa

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Santa Rosa (STS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 30, 2025.

Round-trip from

$286
(Trip.com)

One-way from

$204
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$665
From Chicago (CHI) to Santa Rosa Sonoma County
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One-way flight from Chicago (CHI) to Santa Rosa Sonoma County
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Highest demand for flights based on searches. 12% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Chicago to Santa Rosa

Cheapest flights from Chicago to Santa Rosa
Explore the most affordable flight options available from Chicago to Santa Rosa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.

This Trip.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:08 amORD - STS
1 stop9h 17mMultiple Airlines
Tue 8/1910:00 amSTS - ORD
2 stops17h 40mMultiple Airlines
Deal found 6/28$286
This Trip.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/132:03 pmORD - STS
1 stop7h 40mHawaiian Airlines
Wed 8/202:28 pmSTS - ORD
1 stop7h 31mHawaiian Airlines
Deal found 6/28$303
This Alaska Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:00 amORD - STS
1 stop14h 43mAlaska Airlines
Tue 8/198:01 pmSTS - ORD
1 stop16h 23mAlaska Airlines
Deal found 6/28$318

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Santa Rosa that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 30, 2025.
Use the filters below to find and compare flights from Chicago to Santa Rosa that are best for you.

Fly from

Chicago

Fly to

Santa Rosa

Route

Depart

Return

Price

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 8/12

7:08 am-2:25 pm

1 stop9h 17m

Santa Rosa Sonoma County

Tue 8/19

10:00 am-5:40 am

2 stops17h 40m

$286

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Wed 8/13

2:03 pm-7:43 pm

1 stop7h 40m

Santa Rosa Sonoma County

Wed 8/20

2:28 pm-11:59 pm

1 stop7h 31m

$303

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 8/12

7:00 am-7:43 pm

1 stop14h 43m

Santa Rosa Sonoma County

Tue 8/19

8:01 pm-2:24 pm

1 stop16h 23m

$318

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Sat 8/16

6:00 am-11:37 am

1 stop7h 37m

Santa Rosa Sonoma County

Sat 8/23

12:17 pm-8:57 pm

1 stop6h 40m

$490

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Fri 8/15

1:03 pm-7:09 pm

1 stop8h 06m

$204

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Sun 7/20

5:00 am-12:31 pm

2 stops9h 31m

$415

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Best time to book a flight from Chicago to Santa Rosa

Have a flexible travel schedule? Discover the best time to fly to Santa Rosa from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Santa Rosa

What is the cheapest month to book a flight from Chicago to Santa Rosa?

Currently, February is the cheapest month in which you can book a flight from Chicago to Santa Rosa (average of $202). Flying from Chicago to Santa Rosa in June is currently the most expensive (average of $395). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to STS?

Find hourly flight availability from Chicago to Santa Rosa. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 30, 2025.

It’s optimal to fly from Chicago to Santa Rosa in the afternoon. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the morning.

How much does it cost to fly round-trip from Chicago to Santa Rosa?

Reviews of airlines servicing Santa Rosa

Get insights into the airlines that provide service to Santa Rosa. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Santa Rosa. Reviews last updated June 30, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Hawaiian Airlines, and American Airlines from Chicago to Santa Rosa to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,529 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Santa Rosa. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Santa Rosa from Chicago?

    Most people fly into Santa Rosa Sonoma County (STS) if they book a flight to Santa Rosa from Chicago. On average, Sonoma County has 0 inbound flights from Chicago per day from 1 airline. Santa Rosa Sonoma County is conveniently located just 7.2 mi from Santa Rosa’s city center.

  • What are the cheapest airlines flying from Chicago to Santa Rosa round-trip?

    Our cheapest airline available from Chicago to Santa Rosa is Hawaiian Airlines. Our recent data shows that you can find tickets from as low as $303 on this airline. An additional option worth looking into is Alaska Airlines, starting at $318. Hawaiian Airlines is currently priced 48% below the average price you’ll pay for this route.

  • Can I find deals for flights from Chicago to Santa Rosa that include hotel bookings?

    Yes. In addition to deals on Chicago to Santa Rosa flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Santa Rosa?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Santa Rosa.

  • Can I find deals for business class flights from Chicago to Santa Rosa?

    Yes. Cheapflights offers flight deals from Chicago to Santa Rosa by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Santa Rosa?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Santa Rosa (average of $202). Flying from Chicago to Santa Rosa in June is currently the most expensive (average of $395). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Santa Rosa

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Santa Rosa

Discover the top airline that operate flights from Chicago to Santa Rosa. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$363Average$658FlexibilityNo cancel feeOn-time71%

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