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Santa Rosa

$135+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 agosto 14, 2025.

Round-trip from

$272
(Alaska Airlines)

One-way from

$135
(Alaska Airlines)

Popular in

December

Cheapest in

November

Average price

$563
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. 9% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 14, 2025.

This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
mié. 10/153:50 pmORD - STS
1 stop9h 26mAlaska Airlines
mar. 10/219:43 amSTS - ORD
2 stops12h 16mAlaska Airlines
Deal found 8/14$272
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
mié. 10/153:50 pmORD - STS
1 stop9h 26mAlaska Airlines
mié. 10/226:25 amSTS - ORD
1 stop10h 34mAlaska Airlines
Deal found 8/14$287
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
mar. 10/147:59 pmORD - STS
1 stop29h 17mAlaska Airlines
mar. 10/219:43 amSTS - ORD
2 stops12h 16mAlaska Airlines
Deal found 8/14$290
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
sáb. 11/17:00 amORD - STS
1 stop14h 27mAlaska Airlines
mié. 11/56:49 amSTS - ORD
1 stop10h 10mAlaska Airlines
Deal found 8/14$293
This Trip.com deal was found by Cheapflights users on 8/12. 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.
sáb. 9/2012:05 pmORD - STS
1 stop10h 18mMultiple Airlines
mar. 9/237:03 amSTS - ORD
1 stop9h 11mMultiple Airlines
Deal found 8/12$301
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
mar. 10/148:20 amORD - STS
1 stop27h 47mAlaska Airlines
mié. 10/226:25 amSTS - ORD
1 stop15h 34mAlaska Airlines
Deal found 8/14$304
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
mié. 10/153:50 pmORD - STS
1 stop9h 26mAlaska Airlines
lun. 10/207:42 pmSTS - ORD
1 stop17h 08mAlaska Airlines
Deal found 8/14$306
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
sáb. 10/188:00 amORD - STS
1 stop7h 36mAlaska Airlines
mar. 10/216:25 amSTS - ORD
1 stop30h 25mAlaska Airlines
Deal found 8/14$311
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
mié. 10/153:50 pmORD - STS
1 stop9h 26mAlaska Airlines
jue. 10/236:25 amSTS - ORD
1 stop15h 34mAlaska Airlines
Deal found 8/14$316

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 agosto 14, 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

sáb. 10/18

3:50 pm-11:16 pm

1 stop9h 26m

Santa Rosa Sonoma County

sáb. 10/25

6:25 am-11:59 pm

1 stop15h 34m

$287

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mar. 10/14

7:59 pm-11:16 pm

1 stop29h 17m

Santa Rosa Sonoma County

mar. 10/21

9:43 am-11:59 pm

2 stops12h 16m

$290

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

sáb. 11/1

10:00 am-10:05 pm

1 stop14h 05m

Santa Rosa Sonoma County

mié. 11/5

6:49 am-6:59 pm

1 stop10h 10m

$293

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

sáb. 9/20

12:05 pm-8:23 pm

1 stop10h 18m

Santa Rosa Sonoma County

mar. 9/23

7:03 am-6:14 pm

1 stop9h 11m

$301

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

sáb. 10/18

3:50 pm-11:16 pm

1 stop9h 26m

Santa Rosa Sonoma County

lun. 10/20

7:42 pm-2:50 pm

1 stop17h 08m

$306

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mié. 10/15

3:50 pm-11:16 pm

1 stop9h 26m

Santa Rosa Sonoma County

lun. 10/20

7:42 pm-2:50 pm

1 stop17h 08m

$306

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mié. 10/29

9:20 am-2:24 pm

1 stop7h 04m

$135

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

sáb. 10/4

3:50 pm-11:16 pm

1 stop9h 26m

$135

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mar. 12/16

2:59 pm-10:46 pm

1 stop9h 47m

$135

ChicagoSanta Rosa

ORD - STS

ORDSTS

Chicago O'Hare Intl

mar. 10/28

9:20 am-2:24 pm

1 stop7h 04m

$135

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 14 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 agosto 14, 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.

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 agosto 14, 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

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

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

  • What is the cheapest airline to fly 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 $363 on this airline. American Airlines is currently priced 40% 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 airline flying from Chicago to Santa Rosa

Discover the top airline 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$363Average$658FlexibilityNo cancel feeOn-time71%

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