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Santa Rosa

$99+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap 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 February 3, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 4/237:59 pm
ORD
-
STS
1 stop29h 28m
Alaska Airlines
Thu 4/307:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Deal found 2/2$283
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 3/25:29 pm
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Tue 3/1010:51 am
STS
-
ORD
1 stop26h 07m
Alaska Airlines
Deal found 2/2$313
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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.
Sat 3/143:54 pm
ORD
-
STS
2 stops19h 20m
Alaska Airlines
Thu 3/197:00 am
STS
-
ORD
1 stop10h 02m
Alaska Airlines
Deal found 2/3$318
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 3/23:54 pm
ORD
-
STS
1 stop9h 56m
Alaska Airlines
Mon 3/96:37 pm
STS
-
ORD
1 stop27h 22m
Alaska Airlines
Deal found 2/2$333
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Sat 2/287:00 am
ORD
-
STS
1 stop16h 52m
Alaska Airlines
Wed 3/48:00 am
STS
-
ORD
2 stops13h 56m
Alaska Airlines
Deal found 2/2$348
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Sat 2/287:00 am
ORD
-
STS
1 stop16h 52m
Alaska Airlines
Wed 3/1110:51 am
STS
-
ORD
1 stop11h 08m
Alaska Airlines
Deal found 2/2$353
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 4/97:59 pm
ORD
-
STS
1 stop29h 14m
Alaska Airlines
Sun 4/129:50 am
STS
-
ORD
1 stop26h 31m
Alaska Airlines
Deal found 2/1$363

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$283
(Alaska Airlines)

One-way from

$99
(Alaska Airlines)

Popular in

September

Cheapest in

January

Average price

$457
Provider with most accurate pricing for Chicago (CHI)-Santa Rosa Sonoma County flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Santa Rosa Sonoma County flights.
Search Deals
From Chicago (CHI) to Santa Rosa Sonoma County
Search Deals
One-way flight from Chicago (CHI) to Santa Rosa Sonoma County
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($128 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 3, 2026.
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

Mon 3/2

3:54 pm-11:50 pm

1 stop9h 56m

Santa Rosa Sonoma County

Wed 3/11

10:51 am-11:59 pm

1 stop11h 08m

$313

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Mon 3/2

5:29 pm-11:50 pm

1 stop8h 21m

Santa Rosa Sonoma County

Tue 3/10

10:51 am-2:58 pm

1 stop26h 07m

$313

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Sat 3/14

3:54 pm-9:14 am

2 stops19h 20m

Santa Rosa Sonoma County

Thu 3/19

7:00 am-7:02 pm

1 stop10h 02m

$318

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Mon 3/2

3:54 pm-11:50 pm

1 stop9h 56m

Santa Rosa Sonoma County

Mon 3/9

6:37 pm-11:59 pm

1 stop27h 22m

$333

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Sat 2/28

7:00 am-9:52 pm

1 stop16h 52m

Santa Rosa Sonoma County

Wed 3/4

8:00 am-11:56 pm

2 stops13h 56m

$348

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Sat 2/28

7:00 am-9:52 pm

1 stop16h 52m

Santa Rosa Sonoma County

Wed 3/11

10:51 am-11:59 pm

1 stop11h 08m

$353

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Sat 2/28

7:00 am-9:52 pm

1 stop16h 52m

Santa Rosa Sonoma County

Tue 3/10

10:51 am-11:59 pm

1 stop11h 08m

$353

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Thu 4/9

7:59 pm-11:13 pm

1 stop29h 14m

Santa Rosa Sonoma County

Sun 4/12

7:00 am-2:21 pm

1 stop29h 21m

$353

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 3/24

4:10 pm-11:13 pm

1 stop9h 03m

$99

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Fri 4/24

3:52 pm-11:27 pm

1 stop9h 35m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 19 results
1
2

Compare providers for flights from Chicago to Santa Rosa

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Santa Rosa in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Santa Rosa flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Santa Rosa flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Santa Rosa flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Santa Rosa flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Santa Rosa flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $130). Flying from Chicago to Santa Rosa in June is currently the most expensive (average of $196). 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.

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 February 3, 2026.
Peruse reviews from past customers who have flown with Alaska 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
11,833 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,833 reviews
Alaska Airlines
8.0
Very good
11,833 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,218 reviews
Alaska Airlines
8.0
Very good
11,833 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 2 airlines. Santa Rosa Sonoma County is conveniently located just 7.2 mi from Santa Rosa’s city center.

  • How long is the flight from Chicago to Santa Rosa?

    There are many flights that can get you from Chicago to Santa Rosa in 9h 56m. Fly via Alaska Airlines to get the fastest option. There are 1842 mi between Chicago and Santa Rosa.

  • 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 $444 on this airline. An additional option worth looking into is American Airlines, starting at $511. Hawaiian Airlines is currently priced 17% 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 $130). Flying from Chicago to Santa Rosa in June is currently the most expensive (average of $196). 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

Traveling to a place near Santa Rosa?

Book flights to Santa Rosa if you plan to visit one of these locations
Fort Bragg
Ukiah

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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 2 airlines flying from Chicago to Santa Rosa

Discover the top 2 airlines 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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$444Average$547FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$511Average$788FlexibilityNo cancel feeOn-time71%

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