HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$146+ Cheap flights from Santa Rosa (STS) to Chicago (CHI)

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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Santa Rosa to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Santa Rosa to Chicago

Cheapest flights from Santa Rosa to Chicago
Explore the most affordable flight options available from Santa Rosa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/318:17 pmSTS - ORD
1 stop14h 59mAlaska Airlines
Sun 1/48:39 amORD - STS
1 stop17h 20mAlaska Airlines
Deal found 12/16$618
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Mon 12/228:17 pmSTS - ORD
1 stop6h 45mAlaska Airlines
Thu 12/258:39 amORD - STS
1 stop8h 05mAlaska Airlines
Deal found 12/16$909
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Sat 12/206:08 pmSTS - ORD
1 stop8h 55mAlaska Airlines
Thu 12/258:39 amORD - STS
1 stop8h 05mAlaska Airlines
Deal found 12/16$997
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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 12/237:42 pmSTS - ORD
1 stop22h 20mAlaska Airlines
Sat 12/278:58 pmORD - STS
1 stop29h 01mAlaska Airlines
Deal found 12/16$1,013
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/188:17 pmSTS - ORD
1 stop6h 45mAlaska Airlines
Wed 12/243:33 pmORD - STS
1 stop23h 59mAlaska Airlines
Deal found 12/16$1,016
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Sat 12/206:08 pmSTS - ORD
1 stop8h 55mAlaska Airlines
Wed 12/243:33 pmORD - STS
1 stop23h 59mAlaska Airlines
Deal found 12/16$1,104
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:59 pmSTS - ORD
1 stop9h 17mAmerican Airlines
Mon 12/2910:40 amORD - STS
1 stop7h 11mAmerican Airlines
Deal found 12/16$1,118
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Sun 12/212:24 pmSTS - ORD
1 stop7h 35mAlaska Airlines
Thu 12/258:39 amORD - STS
1 stop8h 05mAlaska Airlines
Deal found 12/16$1,130
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Mon 12/228:17 pmSTS - ORD
1 stop6h 45mAlaska Airlines
Sat 12/278:58 pmORD - STS
1 stop29h 01mAlaska Airlines
Deal found 12/16$1,150

Find flight deals from Santa Rosa to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Santa Rosa (STS) to Chicago (CHI). 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 December 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$279
(Alaska Airlines)

One-way from

$146
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$325
Provider with most accurate pricing for Santa Rosa Sonoma County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Santa Rosa Sonoma County-Chicago (CHI) flights.
Search Deals
From Santa Rosa Sonoma County to Chicago (CHI)
Search Deals
One-way flight from Santa Rosa Sonoma County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Santa Rosa to Chicago 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 December 18, 2025.
Use the filters below to find and compare flights from Santa Rosa to Chicago that are best for you.

Fly from

Santa Rosa

Fly to

Chicago

Route

Depart

Return

Price

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sat 2/21

10:51 am-11:59 pm

1 stop11h 08m

Chicago O'Hare Intl

Wed 2/25

8:20 am-7:02 pm

1 stop12h 42m

$279

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 2/3

2:30 pm-11:37 pm

1 stop7h 07m

Chicago O'Hare Intl

Thu 2/5

3:44 pm-11:11 pm

1 stop9h 27m

$288

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 1/27

2:30 pm-11:37 pm

1 stop7h 07m

Chicago O'Hare Intl

Sun 2/1

9:00 am-2:29 pm

1 stop7h 29m

$289

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 2/2

9:38 am-2:29 pm

1 stop26h 51m

Chicago O'Hare Intl

Thu 2/5

3:44 pm-11:11 pm

1 stop9h 27m

$290

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Thu 2/5

6:50 am-5:10 pm

2 stops8h 20m

Chicago O'Hare Intl

Fri 2/6

3:35 pm-8:58 am

2 stops19h 23m

$293

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 1/27

6:50 am-5:10 pm

2 stops8h 20m

Chicago O'Hare Intl

Mon 2/2

8:00 am-12:22 pm

2 stops30h 22m

$293

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 1/27

6:50 am-5:10 pm

2 stops8h 20m

Chicago O'Hare Intl

Thu 2/5

3:44 pm-11:11 pm

1 stop9h 27m

$296

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Thu 2/5

6:50 am-5:10 pm

2 stops8h 20m

$146

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Thu 1/15

9:33 pm-11:50 pm

1 stop24h 17m

$167

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Thu 12/25

8:17 pm-5:02 am

1 stop6h 45m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 17 results
1
2
  • Most accurate provider: When it comes to deals on Santa Rosa-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Santa Rosa-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Santa Rosa-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Santa Rosa-Chicago 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 Santa Rosa-Chicago 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 Santa Rosa to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Santa Rosa 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 Santa Rosa to Chicago

What is the cheapest month to book a flight from Santa Rosa to Chicago?

Currently, April is the cheapest month in which you can book a flight from Santa Rosa to Chicago (average of $126). Flying from Santa Rosa to Chicago in December is currently the most expensive (average of $233). 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 STS to CHI?

Find hourly flight availability from Santa Rosa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

One of the essential ways to save on airfare from Santa Rosa to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 2% on airfare.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated December 18, 2025.
See what other customers who have flown with Alaska Airlines and American Airlines from Santa Rosa to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,474 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,474 reviews
Alaska Airlines
8.0
Very good
11,474 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,053 reviews
Alaska Airlines
8.0
Very good
11,474 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

Find useful and relevant information for your journey from Santa Rosa to Chicago. 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 from for flights from Santa Rosa to Chicago?

    For a flight from Santa Rosa to Chicago, you will be flying from Sonoma County. Santa Rosa Sonoma County (STS) is just 7.2 mi from the center of the city. Sonoma County is the only Santa Rosa airport and it handles 0 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Santa Rosa Sonoma County on a regular basis.

  • How long is the flight from Santa Rosa to Chicago?

    A quick flight from Santa Rosa to Chicago can take about 11h 08m. Alaska Airlines provides one of the quickest options available for as low as $279. There are 1842 mi between Santa Rosa and Chicago.

  • What are the cheapest airlines flying from Santa Rosa to Chicago round-trip?

    Currently priced at $292, Alaska Airlines will fly you from Santa Rosa to Chicago and back. In addition to Alaska Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $316. You may be able to fly from Santa Rosa to Chicago for 42% less than the average price by searching for these airlines.

  • Can I find deals for flights from Santa Rosa to Chicago that include hotel bookings?

    Yes. In addition to deals on Santa Rosa to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Santa Rosa to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Santa Rosa to Chicago.

  • Can I find deals for business class flights from Santa Rosa to Chicago?

    Yes. Cheapflights offers flight deals from Santa Rosa to Chicago 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 Santa Rosa to Chicago?

    Currently, April is the cheapest month in which you can book a flight from Santa Rosa to Chicago (average of $126). Flying from Santa Rosa to Chicago in December is currently the most expensive (average of $233). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Santa Rosa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Los Angeles to Midway flights
Ontario to O'Hare Intl flights
San Diego to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
San Francisco to Midway flights
Sacramento to O'Hare Intl flights
San Jose to O'Hare Intl flights
Los Angeles to St. Louis flights
Burbank to O'Hare Intl flights
Las Vegas to Midway flights
San Francisco to St. Louis flights
San Diego to Midway flights
Sacramento to Midway flights
Palm Springs to O'Hare Intl flights
Ontario to Midway flights
Oakland to O'Hare Intl flights
Santa Ana to Midway flights
San Jose to Midway flights
Fresno to O'Hare Intl flights
Reno to O'Hare Intl flights
Ontario to St. Louis flights
San Diego to St. Louis flights
Oakland to Midway flights
Sacramento to St. Louis flights
Las Vegas to St. Louis flights
Burbank to Midway flights
Long Beach to O'Hare Intl flights
Burbank to St. Louis flights
Santa Barbara to O'Hare Intl flights
Santa Ana to St. Louis flights
Los Angeles to Moline flights
San Jose to St. Louis flights
Monterey to O'Hare Intl flights
Los Angeles to Rockford flights
Bakersfield to O'Hare Intl flights
Reno to Midway flights
Fresno to Midway flights
Palm Springs to Midway flights
Los Angeles to Peoria flights
San Luis Obispo to O'Hare Intl flights
Santa Ana to Peoria flights
Long Beach to Midway flights
Long Beach to St. Louis flights
Ontario to Peoria flights
Reno to St. Louis flights
Santa Barbara to St. Louis flights
San Francisco to Peoria flights

Top 2 airlines flying from Santa Rosa to Chicago

Discover the top 2 airlines that operate flights from Santa Rosa to Chicago. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$292Average$506FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$316Average$653FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.