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Santa Rosa

$138+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$277
(Alaska Airlines)

One-way from

$138
(Alaska Airlines)

Popular in

December

Cheapest in

November

Average price

$755
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. 3% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/16. 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 10/143:50 pmORD - STS
1 stop9h 26mAlaska Airlines
Tue 10/217:53 pmSTS - ORD
1 stop16h 57mAlaska Airlines
Deal found 9/16$277
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 10/143:50 pmORD - STS
1 stop9h 26mAlaska Airlines
Sat 10/186:25 amSTS - ORD
1 stop15h 34mAlaska Airlines
Deal found 9/15$297
This Hawaiian Airlines deal was found by Cheapflights users on 9/16. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/143:50 pmORD - STS
1 stop9h 26mHawaiian Airlines
Tue 10/217:05 amSTS - ORD
1 stop7h 58mHawaiian Airlines
Deal found 9/16$305
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 10/143:50 pmORD - STS
1 stop9h 26mAlaska Airlines
Wed 10/156:25 amSTS - ORD
2 stops15h 34mAlaska Airlines
Deal found 9/15$311
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 12/43:05 pmORD - STS
1 stop10h 03mAlaska Airlines
Mon 12/86:43 pmSTS - ORD
1 stop22h 11mAlaska Airlines
Deal found 9/17$317
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/86:00 amORD - STS
1 stop9h 36mAlaska Airlines
Tue 10/146:25 amSTS - ORD
1 stop10h 34mAlaska Airlines
Deal found 9/14$318
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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 10/243:50 pmORD - STS
1 stop9h 26mAlaska Airlines
Tue 10/286:49 amSTS - ORD
1 stop10h 10mAlaska Airlines
Deal found 9/16$332
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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 10/216:00 amORD - STS
1 stop9h 36mAlaska Airlines
Tue 10/217:53 pmSTS - ORD
1 stop26h 06mAlaska Airlines
Deal found 9/16$338
This Trip.com deal was found by Cheapflights users on 9/14. 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 10/87:15 amORD - STS
2 stops12h 56mMultiple Airlines
Tue 10/149:43 amSTS - ORD
2 stops36h 10mMultiple Airlines
Deal found 9/14$343

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 September 17, 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 10/14

3:50 pm-11:16 pm

1 stop9h 26m

Santa Rosa Sonoma County

Tue 10/21

9:43 am-11:59 pm

2 stops12h 16m

$283

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Wed 10/15

3:50 pm-11:16 pm

1 stop9h 26m

Santa Rosa Sonoma County

Sat 10/18

6:25 am-11:59 pm

1 stop15h 34m

$297

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 10/21

6:00 am-3:33 pm

2 stops11h 33m

Santa Rosa Sonoma County

Tue 10/21

7:53 pm-2:50 pm

1 stop16h 57m

$311

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Tue 10/14

3:50 pm-11:16 pm

1 stop9h 26m

Santa Rosa Sonoma County

Wed 10/15

6:25 am-11:59 pm

2 stops15h 34m

$311

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Wed 10/22

3:50 pm-11:16 pm

1 stop9h 26m

Santa Rosa Sonoma County

Tue 10/28

6:49 am-12:24 am

2 stops15h 35m

$311

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Sat 11/8

9:20 am-11:57 pm

1 stop16h 37m

Santa Rosa Sonoma County

Sat 11/15

6:49 am-7:55 pm

1 stop11h 06m

$318

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Wed 10/8

6:00 am-1:36 pm

1 stop9h 36m

Santa Rosa Sonoma County

Tue 10/14

6:25 am-6:59 pm

1 stop10h 34m

$318

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Thu 12/4

3:05 pm-11:08 pm

1 stop10h 03m

Santa Rosa Sonoma County

Mon 12/8

8:03 pm-4:55 pm

2 stops18h 52m

$325

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Fri 10/24

3:50 pm-11:16 pm

1 stop9h 26m

Santa Rosa Sonoma County

Tue 10/28

6:49 am-6:59 pm

1 stop10h 10m

$332

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Sat 11/8

2:54 pm-11:57 pm

1 stop11h 03m

Santa Rosa Sonoma County

Fri 11/14

7:46 pm-1:54 pm

1 stop16h 08m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 20 results
1
2

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 September 17, 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 September 17, 2025.
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
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 26m. 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 American Airlines. Our recent data shows that you can find tickets from as low as $384 on this airline. An additional option worth looking into is Hawaiian Airlines, starting at $444. American Airlines is currently priced 38% 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

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$384Average$743FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$444Average$547FlexibilityNo cancel feeOn-time85%

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