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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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
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 March 24, 2026.

This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 4/157:00 am
STS
-
ORD
1 stop10h 02m
Alaska Airlines
Tue 4/214:10 pm
ORD
-
STS
1 stop9h 03m
Alaska Airlines
Deal found 3/23$287
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 5/167:06 am
STS
-
ORD
1 stop9h 44m
Alaska Airlines
Mon 5/187:59 pm
ORD
-
STS
1 stop29h 57m
Alaska Airlines
Deal found 3/23$309
This Alaska Airlines deal was found by Cheapflights users on 3/19. 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 4/287:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Sat 5/26:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Deal found 3/19$322
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 4/157:00 am
STS
-
ORD
1 stop10h 02m
Alaska Airlines
Thu 4/233:52 pm
ORD
-
STS
1 stop9h 35m
Alaska Airlines
Deal found 3/23$329
This Alaska Airlines deal was found by Cheapflights users on 3/22. 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 5/167:06 am
STS
-
ORD
1 stop9h 44m
Alaska Airlines
Wed 5/209:00 am
ORD
-
STS
1 stop16h 50m
Alaska Airlines
Deal found 3/22$342
This Expedia deal was found by Cheapflights users on 3/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:23 am
STS
-
ORD
2 stops14h 36m
Alaska Airlines
Wed 5/63:52 pm
ORD
-
STS
1 stop21h 06m
Alaska Airlines
Deal found 3/21$347
This Southwest deal was found by Cheapflights users on 3/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
STS
-
ORD
2 stops14h 55m
Southwest
Tue 5/1211:55 am
ORD
-
STS
2 stops12h 15m
Southwest
Deal found 3/22$348
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 4/167:00 am
STS
-
ORD
1 stop10h 02m
Alaska Airlines
Wed 4/226:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Deal found 3/23$351
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 4/146:53 pm
STS
-
ORD
1 stop9h 46m
Alaska Airlines
Wed 4/226:00 am
ORD
-
STS
1 stop8h 21m
Alaska Airlines
Deal found 3/23$357
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 4/157:00 am
STS
-
ORD
1 stop10h 02m
Alaska Airlines
Sat 4/188:20 am
ORD
-
STS
1 stop13h 00m
Alaska Airlines
Deal found 3/23$362
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 4/146:53 pm
STS
-
ORD
1 stop9h 46m
Alaska Airlines
Fri 4/174:10 pm
ORD
-
STS
1 stop9h 03m
Alaska Airlines
Deal found 3/23$364
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 5/127:23 am
STS
-
ORD
1 stop9h 40m
Alaska Airlines
Mon 5/187:59 pm
ORD
-
STS
1 stop29h 57m
Alaska Airlines
Deal found 3/23$365

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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$287
(Alaska Airlines)

One-way from

$144
(Alaska Airlines)

Popular in

May

Cheapest in

November

Average price

$403
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. 18% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($54 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 24, 2026.
Use the filters below to find and compare flights from Santa Rosa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 4/28

7:23 am-7:03 pm

1 stop9h 40m

Chicago O'Hare Intl

Sat 5/2

6:00 am-12:21 pm

1 stop8h 21m

$322

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

$370

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Fri 5/8

7:23 am-7:03 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 5/15

2:10 pm-11:50 pm

1 stop11h 40m

$371

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 5/18

8:26 pm-6:20 am

1 stop7h 54m

Chicago O'Hare Intl

Sat 5/23

9:00 am-11:28 pm

1 stop16h 28m

$401

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 5/19

7:01 am-6:50 pm

1 stop9h 49m

Chicago O'Hare Intl

Wed 5/20

6:00 am-7:59 pm

2 stops15h 59m

$410

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Thu 4/23

7:00 am-11:59 pm

2 stops14h 59m

Chicago O'Hare Intl

Mon 4/27

3:52 pm-11:27 pm

1 stop9h 35m

$467

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Thu 7/2

6:26 am-7:00 pm

1 stop10h 34m

Chicago O'Hare Intl

Tue 7/7

6:22 am-5:16 pm

2 stops12h 54m

$486
Quickest round-trip

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 9/15

3:18 pm-11:59 pm

1 stop6h 41m

Chicago O'Hare Intl

Sun 9/20

2:54 pm-10:53 pm

1 stop9h 59m

$489

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Wed 9/16

3:18 pm-11:59 pm

1 stop6h 41m

Chicago O'Hare Intl

Sun 9/20

2:54 pm-10:53 pm

1 stop9h 59m

$489
Cheapest one-way

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sat 4/18

7:00 am-7:02 pm

1 stop10h 02m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 20 resultsSorted by cheapest first
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 $115). 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 March 24, 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
7.9
Good
12,101 reviews

Food

7.0

Crew

8.5

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Alaska Airlines
7.9
Good
12,101 reviews
Alaska Airlines
7.9
Good
12,101 reviews

Food

7.0

Crew

8.5

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

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. 1 airline has 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 $322. There are 1842 mi between Santa Rosa and Chicago.

  • What is the cheapest airline to fly 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. You may be able to fly from Santa Rosa to Chicago for 37% less than the average price by searching for this airline.

  • 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 $115). 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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Alternative routes for Santa Rosa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Santa Rosa to Chicago

Discover the top airline 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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$292Average$408FlexibilityNo cancel feeOn-time75%

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