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$109+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$234
(Mytrip)

One-way from

$109
(Mytrip)

Popular in

February

Cheapest in

December

Average price

$868
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
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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. 16% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/39:10 amSTS - ORD
1 stop18h 57mMultiple Airlines
Thu 3/69:47 pmORD - STS
1 stop17h 35mMultiple Airlines
Deal found 2/18$234
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/94:17 pmSTS - ORD
1 stop6h 23mAmerican Airlines
Tue 4/156:00 amORD - STS
1 stop8h 17mAmerican Airlines
Deal found 2/19$323
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 4/93:09 pmSTS - ORD
2 stops12h 31mAlaska Airlines
Tue 4/153:16 pmORD - STS
1 stop20h 09mAlaska Airlines
Deal found 2/19$379
This Hawaiian Airlines deal was found by Cheapflights users on 2/20. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:00 pmSTS - ORD
1 stop8h 04mHawaiian Airlines
Fri 10/107:45 amORD - STS
1 stop8h 03mHawaiian Airlines
Deal found 2/20$565

Find flights from Santa Rosa to Chicago within your budget

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 20, 2025.

Fly from

Santa Rosa

Fly to

Chicago

Route

Depart

Return

Price

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 3/3

9:10 am-6:07 am

1 stop18h 57m

Chicago O'Hare Intl

Thu 3/6

9:47 pm-1:22 pm

1 stop17h 35m

$234

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Wed 4/9

4:17 pm-12:40 am

1 stop6h 23m

Chicago O'Hare Intl

Tue 4/15

6:00 am-12:17 pm

1 stop8h 17m

$323

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Wed 4/9

3:09 pm-5:40 am

2 stops12h 31m

Chicago O'Hare Intl

Tue 4/15

3:16 pm-9:25 am

1 stop20h 09m

$379

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 3/31

9:16 am-8:13 pm

2 stops32h 57m

$109

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Wed 5/7

12:30 pm-9:09 pm

1 stop6h 39m

$162

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 5/6

12:45 pm-6:05 am

2 stops15h 20m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Santa Rosa to Chicago

Get recent, data-driven insights about flights from Santa Rosa to Chicago including ideal travel times, pricing trends, and more.

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 February 20, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 20, 2025.
Alaska Airlines
8.0
Very good
9,697 reviews

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,697 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

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

    Currently priced at $323, American Airlines will fly you from Santa Rosa to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Alaska Airlines for as low as $379. 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, 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 Santa Rosa?

Book flights to Santa Rosa if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$318Average$693FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$333Average$629FlexibilityNo cancel feeOn-time75%
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