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$99+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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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 February 5, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 5/27:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Thu 5/73:52 pm
ORD
-
STS
1 stop9h 35m
Alaska Airlines
Deal found 2/2$210
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 5/27:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Wed 5/66:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Deal found 2/2$217
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 3/177:57 pm
STS
-
ORD
1 stop8h 42m
Alaska Airlines
Tue 3/314:13 pm
ORD
-
STS
1 stop9h 00m
Alaska Airlines
Deal found 2/2$230
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 3/316:53 pm
STS
-
ORD
1 stop9h 46m
Alaska Airlines
Wed 4/154:10 pm
ORD
-
STS
1 stop9h 03m
Alaska Airlines
Deal found 2/2$253
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 3/38:00 am
STS
-
ORD
1 stop27h 11m
Alaska Airlines
Tue 3/107:00 am
ORD
-
STS
1 stop16h 52m
Alaska Airlines
Deal found 2/2$260
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 4/66:53 pm
STS
-
ORD
1 stop9h 46m
Alaska Airlines
Wed 4/154:10 pm
ORD
-
STS
1 stop9h 03m
Alaska Airlines
Deal found 2/2$263
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 5/11:13 pm
STS
-
ORD
1 stop8h 46m
Alaska Airlines
Wed 5/66:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Deal found 2/2$270
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 3/189:50 am
STS
-
ORD
1 stop7h 12m
Alaska Airlines
Wed 3/254:10 pm
ORD
-
STS
1 stop9h 03m
Alaska Airlines
Deal found 2/2$293
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 4/87:00 am
STS
-
ORD
1 stop10h 02m
Alaska Airlines
Fri 4/104:10 pm
ORD
-
STS
1 stop9h 03m
Alaska Airlines
Deal found 2/2$302

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$210
(Alaska Airlines)

One-way from

$99
(Orbitz)

Popular in

May

Cheapest in

November

Average price

$814
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. 11% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 5, 2026.
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 5/2

7:23 am-7:03 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 5/7

3:52 pm-11:27 pm

1 stop9h 35m

$210

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sat 5/2

7:23 am-7:03 pm

1 stop9h 40m

Chicago O'Hare Intl

Wed 5/6

6:00 am-11:59 pm

2 stops19h 59m

$265

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Fri 5/1

1:13 pm-11:59 pm

1 stop8h 46m

Chicago O'Hare Intl

Wed 5/6

6:00 am-12:21 pm

1 stop8h 21m

$270

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 3/3

6:50 pm-1:11 pm

1 stop16h 21m

Chicago O'Hare Intl

Tue 3/10

8:20 am-7:17 pm

2 stops12h 57m

$283

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 3/17

7:57 pm-6:39 am

1 stop8h 42m

Chicago O'Hare Intl

Tue 3/31

2:09 pm-6:01 pm

2 stops29h 52m

$285

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Wed 4/8

7:00 am-7:02 pm

1 stop10h 02m

Chicago O'Hare Intl

Fri 4/10

4:10 pm-11:13 pm

1 stop9h 03m

$302

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 3/31

7:05 am-11:59 pm

2 stops14h 54m

Chicago O'Hare Intl

Wed 4/15

4:10 pm-11:13 pm

1 stop9h 03m

$308

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 3/31

6:53 pm-6:39 am

1 stop9h 46m

Chicago O'Hare Intl

Thu 4/9

7:59 pm-11:13 pm

1 stop29h 14m

$313

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 4/6

6:53 pm-6:39 am

1 stop9h 46m

Chicago O'Hare Intl

Thu 4/9

7:59 pm-11:13 pm

1 stop29h 14m

$323

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Thu 3/5

7:57 pm-1:11 pm

2 stops15h 14m

Chicago O'Hare Intl

Mon 3/9

3:07 pm-7:02 pm

1 stop29h 55m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 18 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.

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 February 5, 2026.
See what other customers who have flown with Alaska 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
11,839 reviews

Food

7.1

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,839 reviews
Alaska Airlines
8.0
Very good
11,839 reviews

Food

7.1

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 9h 40m. Alaska Airlines provides one of the quickest options available for as low as $210. 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 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

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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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$292Average$408FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$316Average$563FlexibilityNo cancel feeOn-time71%

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