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$162+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 11/227:00 pmSTS - ORD
1 stop8h 01mAlaska Airlines
Tue 12/28:59 pmORD - STS
1 stop19h 37mAlaska Airlines
Deal found 10/29$315
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 11/236:35 amSTS - ORD
1 stop14h 57mAlaska Airlines
Tue 12/28:59 pmORD - STS
1 stop19h 37mAlaska Airlines
Deal found 10/29$332
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 stop16h 55mAlaska Airlines
Sun 1/48:58 pmORD - STS
1 stop16h 25mAlaska Airlines
Deal found 10/30$342
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 11/187:46 pmSTS - ORD
1 stop16h 08mAlaska Airlines
Tue 12/28:59 pmORD - STS
1 stop19h 37mAlaska Airlines
Deal found 10/29$350
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 11/246:35 amSTS - ORD
1 stop14h 57mAlaska Airlines
Tue 12/28:59 pmORD - STS
1 stop19h 37mAlaska Airlines
Deal found 10/29$352
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 12/253:53 pmSTS - ORD
2 stops11h 09mAlaska Airlines
Wed 12/313:37 pmORD - STS
1 stop21h 46mAlaska Airlines
Deal found 10/30$353
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 stop16h 55mAlaska Airlines
Fri 1/28:58 pmORD - STS
1 stop29h 01mAlaska Airlines
Deal found 10/30$362
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 12/253:53 pmSTS - ORD
2 stops11h 09mAlaska Airlines
Sat 1/33:37 pmORD - STS
1 stop10h 22mAlaska Airlines
Deal found 10/30$363
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 12/218:17 pmSTS - ORD
1 stop6h 45mAlaska Airlines
Wed 12/313:37 pmORD - STS
1 stop21h 46mAlaska Airlines
Deal found 10/30$367
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 12/233:53 pmSTS - ORD
2 stops11h 10mAlaska Airlines
Wed 12/313:37 pmORD - STS
1 stop21h 46mAlaska Airlines
Deal found 10/30$373
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 12/218:17 pmSTS - ORD
1 stop6h 45mAlaska Airlines
Sat 1/38:39 amORD - STS
1 stop17h 20mAlaska Airlines
Deal found 10/30$377

Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$287
(Alaska Airlines)

One-way from

$162
(Alaska Airlines)

Popular in

February

Cheapest in

August

Average price

$665
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. 14% potential increase in price ($91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 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

Mon 3/9

6:58 am-11:10 pm

1 stop14h 12m

Chicago O'Hare Intl

Tue 3/10

2:59 pm-10:46 pm

1 stop9h 47m

$287

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sat 11/22

7:00 pm-5:01 am

1 stop8h 01m

Chicago O'Hare Intl

Tue 12/2

8:59 pm-2:36 pm

1 stop19h 37m

$315

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 11/18

7:46 pm-1:54 pm

1 stop16h 08m

Chicago O'Hare Intl

Tue 12/2

8:59 pm-2:36 pm

1 stop19h 37m

$350

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sun 12/21

8:17 pm-5:02 am

1 stop6h 45m

Chicago O'Hare Intl

Wed 12/31

3:37 pm-11:23 am

1 stop21h 46m

$367

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Thu 12/18

7:00 am-8:02 pm

2 stops11h 02m

$162

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Fri 12/19

7:52 pm-11:59 pm

1 stop26h 07m

$172

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 12/23

7:42 pm-2:37 pm

1 stop16h 55m

$192

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sun 12/21

8:17 pm-5:02 am

1 stop6h 45m

$211

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 12/22

8:17 pm-5:02 am

1 stop6h 45m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Compare providers for flights from Santa Rosa to Chicago

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 Santa Rosa to Chicago in October.
ProviderPrice AccuracyTrust Score*
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 Santa Rosa-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Santa Rosa-Chicago flight deals on Cheapflights vs. eDreams >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 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 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 March is currently the most expensive (average of $207). 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 October 30, 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 October 30, 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
11,214 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Crew

8.5

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
11,214 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Crew

8.5

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
11,030 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Crew

8.5

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 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 14h 12m. Alaska Airlines provides one of the quickest options available for as low as $287. 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 46% 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 March is currently the most expensive (average of $207). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$292Average$506FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$316Average$653FlexibilityNo cancel feeOn-time71%

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