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$144+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$277
(Alaska Airlines)

One-way from

$144
(Alaska Airlines)

Popular in

February

Cheapest in

December

Average price

$462
From Santa Rosa Sonoma County to Chicago (CHI)
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One-way flight from Santa Rosa Sonoma County to Chicago (CHI)
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Highest demand for flights based on searches. 20% potential increase in price ($132 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 12/58:00 amSTS - ORD
1 stop8h 54mAlaska Airlines
Tue 12/93:05 pmORD - STS
1 stop10h 03mAlaska Airlines
Deal found 9/14$277
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/219:43 amSTS - ORD
2 stops12h 16mAlaska Airlines
Tue 10/289:20 amORD - STS
1 stop8h 42mAlaska Airlines
Deal found 9/14$283
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/79:43 amSTS - ORD
2 stops12h 16mAlaska Airlines
Sat 10/113:50 pmORD - STS
1 stop9h 26mAlaska Airlines
Deal found 9/14$293
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 11/107:46 pmSTS - ORD
1 stop16h 08mAlaska Airlines
Wed 11/129:20 amORD - STS
1 stop8h 42mAlaska Airlines
Deal found 9/15$297
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 11/107:46 pmSTS - ORD
1 stop16h 08mAlaska Airlines
Sat 11/159:20 amORD - STS
2 stops14h 26mAlaska Airlines
Deal found 9/15$304
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/77:53 pmSTS - ORD
1 stop16h 57mAlaska Airlines
Wed 10/153:50 pmORD - STS
1 stop9h 26mAlaska Airlines
Deal found 9/14$308
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 12/67:50 amSTS - ORD
2 stops14h 09mAlaska Airlines
Thu 12/113:05 pmORD - STS
1 stop10h 03mAlaska Airlines
Deal found 9/14$311
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 12/26:43 pmSTS - ORD
1 stop22h 11mAlaska Airlines
Wed 12/109:15 amORD - STS
1 stop7h 21mAlaska Airlines
Deal found 9/14$317
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 11/177:46 pmSTS - ORD
1 stop16h 08mAlaska Airlines
Tue 11/188:59 pmORD - STS
1 stop16h 21mAlaska Airlines
Deal found 9/14$318
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 11/137:46 pmSTS - ORD
1 stop16h 08mAlaska Airlines
Tue 11/189:20 amORD - STS
1 stop8h 42mAlaska Airlines
Deal found 9/14$320
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 10/207:42 pmSTS - ORD
1 stop17h 08mAlaska Airlines
Tue 10/289:20 amORD - STS
2 stops14h 26mAlaska Airlines
Deal found 9/14$324

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 September 15, 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

Fri 12/5

8:00 am-6:54 pm

1 stop8h 54m

Chicago O'Hare Intl

Tue 12/9

3:05 pm-11:08 pm

1 stop10h 03m

$277

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Wed 10/15

6:25 am-11:59 pm

1 stop15h 34m

Chicago O'Hare Intl

Wed 10/22

3:50 pm-11:16 pm

1 stop9h 26m

$297

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Wed 11/12

6:49 am-11:59 pm

1 stop15h 10m

Chicago O'Hare Intl

Tue 11/18

9:20 am-4:02 pm

1 stop8h 42m

$297

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sat 11/15

6:49 am-7:55 pm

1 stop11h 06m

Chicago O'Hare Intl

Tue 11/18

9:20 am-4:02 pm

1 stop8h 42m

$297

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 11/10

7:46 pm-1:54 pm

1 stop16h 08m

Chicago O'Hare Intl

Tue 11/18

9:20 am-4:02 pm

1 stop8h 42m

$297

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 11/10

7:46 pm-1:54 pm

1 stop16h 08m

Chicago O'Hare Intl

Thu 11/13

9:20 am-4:02 pm

1 stop8h 42m

$297

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 11/11

6:49 am-1:54 pm

1 stop29h 05m

Chicago O'Hare Intl

Tue 11/18

9:20 am-4:02 pm

1 stop8h 42m

$297

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 11/11

7:46 pm-7:55 pm

1 stop22h 09m

Chicago O'Hare Intl

Sat 11/15

9:20 am-9:46 pm

2 stops14h 26m

$304

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 11/10

7:46 pm-1:54 pm

1 stop16h 08m

Chicago O'Hare Intl

Sat 11/15

9:20 am-9:46 pm

2 stops14h 26m

$304

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Fri 11/14

7:46 pm-7:55 pm

1 stop22h 09m

Chicago O'Hare Intl

Tue 11/18

9:20 am-4:02 pm

1 stop8h 42m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 19 results
1
2

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, August is the cheapest month in which you can book a flight from Santa Rosa to Chicago (average of $245). Flying from Santa Rosa to Chicago in March is currently the most expensive (average of $321). 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 September 15, 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 in the morning tend to be the most expensive. A flight at noon could potentially save you up to 6% 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 September 15, 2025.
See what other customers who have flown with 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.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 8h 54m. Alaska Airlines provides one of the quickest options available for as low as $277. 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 $308, 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 40% 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, August is the cheapest month in which you can book a flight from Santa Rosa to Chicago (average of $245). Flying from Santa Rosa to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$308Average$542FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$316Average$653FlexibilityNo cancel feeOn-time71%

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