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Santa Rosa

$130+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
nov. 22 — nov. 291
sáb. 11/22
sáb. 11/29
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 octubre 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$254
(Alaska Airlines)

One-way from

$130
(Alaska Airlines)

Popular in

December

Cheapest in

November

Average price

$638
Provider with most accurate pricing for Chicago (CHI)-Santa Rosa Sonoma County flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Santa Rosa Sonoma County flights.
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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 ($32 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 23, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
mar. 12/28:59 pmORD - STS
1 stop27h 55mAlaska Airlines
mar. 12/98:00 amSTS - ORD
1 stop13h 50mAlaska Airlines
Deal found 10/22$258
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
jue. 12/43:05 pmORD - STS
1 stop9h 49mAlaska Airlines
mié. 12/108:00 amSTS - ORD
1 stop13h 50mAlaska Airlines
Deal found 10/22$259
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
mié. 11/129:20 amORD - STS
1 stop8h 42mAlaska Airlines
mié. 11/192:09 pmSTS - ORD
1 stop7h 50mAlaska Airlines
Deal found 10/22$260
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
mié. 12/33:05 pmORD - STS
1 stop9h 49mAlaska Airlines
mié. 12/106:54 pmSTS - ORD
2 stops9h 27mAlaska Airlines
Deal found 10/22$286
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
jue. 12/43:05 pmORD - STS
1 stop9h 49mAlaska Airlines
jue. 12/117:00 amSTS - ORD
2 stops13h 30mAlaska Airlines
Deal found 10/22$287
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
mié. 11/129:20 amORD - STS
2 stops14h 26mAlaska Airlines
mar. 11/182:09 pmSTS - ORD
1 stop7h 50mAlaska Airlines
Deal found 10/22$292
This Alaska Airlines deal was found by Cheapflights users on 10/21. 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.
vie. 11/148:59 pmORD - STS
1 stop16h 21mAlaska Airlines
dom. 11/166:49 amSTS - ORD
1 stop15h 10mAlaska Airlines
Deal found 10/21$297
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
mié. 12/33:05 pmORD - STS
1 stop9h 49mAlaska Airlines
jue. 12/117:55 pmSTS - ORD
1 stop8h 26mAlaska Airlines
Deal found 10/22$300
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
mié. 12/33:05 pmORD - STS
1 stop9h 49mAlaska Airlines
mar. 12/97:00 amSTS - ORD
2 stops13h 30mAlaska Airlines
Deal found 10/22$306
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
jue. 12/43:05 pmORD - STS
1 stop9h 49mAlaska Airlines
mar. 12/97:00 amSTS - ORD
2 stops13h 30mAlaska Airlines
Deal found 10/22$307
This Alaska Airlines deal was found by Cheapflights users on 10/21. 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.
jue. 11/132:54 pmORD - STS
1 stop11h 03mAlaska Airlines
dom. 11/166:49 amSTS - ORD
1 stop15h 10mAlaska Airlines
Deal found 10/21$312

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 octubre 23, 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

vie. 1/9

9:00 am-2:29 pm

1 stop7h 29m

Santa Rosa Sonoma County

dom. 1/11

6:52 pm-11:37 pm

1 stop26h 45m

$254

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mar. 12/2

8:59 pm-10:54 pm

1 stop27h 55m

Santa Rosa Sonoma County

mar. 12/9

8:00 am-11:50 pm

1 stop13h 50m

$258

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mar. 12/2

8:59 pm-10:54 pm

1 stop27h 55m

Santa Rosa Sonoma County

mié. 12/10

8:00 am-11:50 pm

1 stop13h 50m

$258

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

jue. 12/4

3:05 pm-10:54 pm

1 stop9h 49m

Santa Rosa Sonoma County

mié. 12/10

8:00 am-11:50 pm

1 stop13h 50m

$259

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

jue. 12/4

3:05 pm-10:54 pm

1 stop9h 49m

Santa Rosa Sonoma County

mar. 12/9

8:00 am-11:50 pm

1 stop13h 50m

$259

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mar. 2/24

2:59 pm-10:46 pm

1 stop9h 47m

Santa Rosa Sonoma County

sáb. 2/28

6:58 am-11:10 pm

1 stop14h 12m

$261

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

lun. 3/2

2:59 pm-10:46 pm

1 stop9h 47m

Santa Rosa Sonoma County

vie. 3/6

6:58 am-1:59 pm

1 stop29h 01m

$276

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mié. 11/12

9:20 am-4:02 pm

1 stop8h 42m

Santa Rosa Sonoma County

mié. 12/3

6:43 pm-11:50 pm

1 stop27h 07m

$286

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mié. 12/3

3:05 pm-10:54 pm

1 stop9h 49m

Santa Rosa Sonoma County

jue. 12/11

7:00 am-10:30 pm

2 stops13h 30m

$286

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mié. 12/3

3:05 pm-10:54 pm

1 stop9h 49m

Santa Rosa Sonoma County

mié. 12/10

6:54 pm-6:21 am

2 stops9h 27m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust 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 $198). 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 octubre 23, 2025.

It’s optimal to fly from Chicago to Santa Rosa at noon. By choosing this option you can save up to 53% on the cost of your flight, compared to a flight in the morning.

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 octubre 23, 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
11,155 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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
11,155 reviews
Alaska Airlines
8.0
Very good
11,155 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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
11,028 reviews
Alaska Airlines
8.0
Very good
11,155 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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 7h 29m. 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 37% 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 $198). 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 octubre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$384Average$743FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$444Average$547FlexibilityNo cancel feeOn-time85%

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