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$129+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$250
(Alaska Airlines)

One-way from

$129
(Alaska Airlines)

Popular in

December

Cheapest in

January

Average price

$343
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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High demand for flights, 12% potential price rise
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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 November 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 November 6, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/53:05 pmORD - STS
1 stop9h 49mAlaska Airlines
Mon 12/88:00 amSTS - ORD
1 stop28h 09mAlaska Airlines
Deal found 11/5$250
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/48:59 pmORD - STS
1 stop27h 55mAlaska Airlines
Mon 12/88:00 amSTS - ORD
1 stop28h 09mAlaska Airlines
Deal found 11/5$277
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/246:00 amORD - STS
1 stop18h 17mAlaska Airlines
Mon 1/57:52 pmSTS - ORD
1 stop16h 45mAlaska Airlines
Deal found 11/5$307
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/256:00 amORD - STS
1 stop9h 32mAlaska Airlines
Thu 1/16:00 amSTS - ORD
1 stop22h 29mAlaska Airlines
Deal found 11/5$341
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/256:00 amORD - STS
1 stop9h 32mAlaska Airlines
Wed 12/318:17 pmSTS - ORD
1 stop14h 59mAlaska Airlines
Deal found 11/5$351
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/246:00 amORD - STS
1 stop18h 17mAlaska Airlines
Thu 1/16:00 amSTS - ORD
1 stop22h 29mAlaska Airlines
Deal found 11/5$352
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/208:58 pmORD - STS
1 stop29h 01mAlaska Airlines
Mon 1/57:52 pmSTS - ORD
1 stop22h 10mAlaska Airlines
Deal found 11/5$357
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/246:08 pmORD - STS
1 stop30h 09mAlaska Airlines
Wed 12/318:17 pmSTS - ORD
1 stop14h 59mAlaska Airlines
Deal found 11/5$362
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/196:00 amORD - STS
1 stop9h 32mAlaska Airlines
Mon 1/52:51 pmSTS - ORD
1 stop21h 46mAlaska Airlines
Deal found 11/5$367

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 November 6, 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

Mon 3/2

2:59 pm-10:46 pm

1 stop9h 47m

Santa Rosa Sonoma County

Fri 3/6

6:58 am-1:59 pm

1 stop29h 01m

$265

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Thu 12/4

8:59 pm-10:54 pm

1 stop27h 55m

Santa Rosa Sonoma County

Mon 12/8

8:00 am-2:09 pm

1 stop28h 09m

$277

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Thu 1/29

8:00 am-11:11 pm

2 stops17h 11m

Santa Rosa Sonoma County

Mon 2/2

6:52 pm-11:37 pm

1 stop26h 45m

$278

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Wed 12/24

6:00 am-10:17 pm

1 stop18h 17m

Santa Rosa Sonoma County

Mon 1/5

7:52 pm-2:37 pm

1 stop16h 45m

$307

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Fri 12/5

8:00 am-11:52 pm

2 stops17h 52m

Santa Rosa Sonoma County

Mon 12/8

7:50 am-11:59 pm

2 stops14h 09m

$398

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Thu 11/27

8:00 am-1:49 pm

1 stop7h 49m

Santa Rosa Sonoma County

Wed 12/3

6:43 pm-2:09 pm

1 stop17h 26m

$412

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Fri 11/28

8:00 am-1:49 pm

1 stop7h 49m

Santa Rosa Sonoma County

Wed 12/3

6:43 pm-2:09 pm

1 stop17h 26m

$460

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Fri 11/28

6:00 am-1:49 pm

1 stop9h 49m

Santa Rosa Sonoma County

Thu 12/4

6:43 pm-2:09 pm

1 stop17h 26m

$475

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Wed 3/18

7:45 am-1:48 pm

1 stop8h 03m

Santa Rosa Sonoma County

Wed 3/25

3:00 pm-11:58 pm

1 stop6h 58m

$478

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

Wed 12/3

3:05 pm-10:54 pm

1 stop9h 49m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 15 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Santa Rosa flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 November 6, 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 November 6, 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
11,246 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

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
11,246 reviews
Alaska Airlines
8.0
Very good
11,246 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

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
11,040 reviews
Alaska Airlines
8.0
Very good
11,246 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

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 47m. 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 35% 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$384Average$743FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$444Average$547FlexibilityNo cancel feeOn-time85%

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