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Santa Rosa

$144+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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Find cheap flights from Chicago to Santa Rosa with Cheapflights

1. Tell us where you want to go

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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 March 24, 2026.

This Alaska Airlines deal was found by Cheapflights users on 3/20. 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 4/214:10 pm
ORD
-
STS
1 stop9h 03m
Alaska Airlines
Sat 5/27:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/20$287
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 5/58:50 am
ORD
-
STS
1 stop12h 16m
Alaska Airlines
Wed 5/67:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/23$301
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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.
Wed 4/226:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Wed 4/2910:01 am
STS
-
ORD
1 stop7h 02m
Alaska Airlines
Deal found 3/23$309
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 4/216:00 am
ORD
-
STS
2 stops19h 13m
Alaska Airlines
Tue 4/287:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/23$314
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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.
Wed 4/226:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Sat 5/27:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/20$322
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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 4/214:10 pm
ORD
-
STS
1 stop9h 03m
Alaska Airlines
Fri 5/87:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/20$329
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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.
Wed 4/226:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Wed 5/61:13 pm
STS
-
ORD
1 stop8h 46m
Alaska Airlines
Deal found 3/20$357
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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.
Wed 4/226:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Mon 5/47:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/20$364
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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.
Fri 4/243:52 pm
ORD
-
STS
1 stop9h 35m
Alaska Airlines
Thu 5/77:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/20$371

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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$287
(Alaska Airlines)

One-way from

$144
(Alaska Airlines)

Popular in

February

Cheapest in

January

Average price

$436
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
High demand for flights, 4% potential price rise
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 24, 2026.
Use the filters below to find and compare flights from Chicago to Santa Rosa that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Wed 4/22

6:00 am-12:21 pm

1 stop8h 21m

Santa Rosa Sonoma County

Wed 4/29

10:01 am-7:03 pm

1 stop7h 02m

$309

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 5/5

6:00 am-12:21 pm

1 stop8h 21m

Santa Rosa Sonoma County

Wed 5/6

1:13 pm-11:59 pm

1 stop8h 46m

$357

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Fri 5/8

3:52 pm-11:27 pm

1 stop9h 35m

Santa Rosa Sonoma County

Mon 5/11

10:01 am-7:03 pm

1 stop7h 02m

$445

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 9/15

2:54 pm-4:05 pm

2 stops27h 11m

Santa Rosa Sonoma County

Sat 9/19

3:18 pm-11:59 pm

1 stop6h 41m

$456

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Thu 8/20

2:54 pm-10:53 pm

1 stop9h 59m

Santa Rosa Sonoma County

Mon 8/24

1:26 pm-11:59 pm

2 stops32h 33m

$476

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Thu 5/28

6:00 am-12:17 pm

1 stop8h 17m

Santa Rosa Sonoma County

Tue 6/9

7:01 am-6:50 pm

1 stop9h 49m

$492

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 7/28

6:00 am-12:17 pm

1 stop8h 17m

Santa Rosa Sonoma County

Sat 8/1

7:03 pm-5:02 am

1 stop7h 59m

$519

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 8/18

6:00 am-12:17 pm

1 stop8h 17m

Santa Rosa Sonoma County

Tue 8/18

7:03 pm-5:02 am

1 stop7h 59m

$519
Cheapest one-way

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 4/28

3:52 pm-10:58 am

1 stop21h 06m

$149

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 6/2

2:10 pm-11:56 pm

1 stop11h 46m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

Showing 1-10 of 17 resultsSorted by cheapest first
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 March.
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, May is the cheapest month in which you can book a flight from Chicago to Santa Rosa (average of $134). Flying from Chicago to Santa Rosa in February is currently the most expensive (average of $217). 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.

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 March 24, 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
7.9
Good
12,105 reviews

Boarding

8.1

Overall

7.9

Comfort

7.8

Entertainment

7.0

Crew

8.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Alaska Airlines
7.9
Good
12,105 reviews
Alaska Airlines
7.9
Good
12,105 reviews

Boarding

8.1

Overall

7.9

Comfort

7.8

Entertainment

7.0

Crew

8.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
American Airlines
7.1
Good
11,491 reviews
Alaska Airlines
7.9
Good
12,105 reviews

Boarding

8.1

Overall

7.9

Comfort

7.8

Entertainment

7.0

Crew

8.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

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 8h 21m. Fly via Alaska Airlines or Southwest to get the fastest option. There are 1842 mi between Chicago and Santa Rosa. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $478. Hawaiian Airlines is currently priced 24% 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, May is the cheapest month in which you can book a flight from Chicago to Santa Rosa (average of $134). Flying from Chicago to Santa Rosa in February is currently the most expensive (average of $217). 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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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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$444Average$547FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$478Average$749FlexibilityNo cancel feeOn-time71%

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