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

Currently priced at $272, 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 Hawaiian Airlines for as low as $305. You may be able to fly from Santa Rosa to Chicago for 48% less than the average price by searching for these airlines.

What is the cheapest day to fly from Santa Rosa to Chicago?

Travelers seeking maximum savings on their Santa Rosa to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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.

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).

What is the cheapest day to fly round-trip from Santa Rosa to Chicago?

Users have found that flying from Santa Rosa to Chicago on a Saturday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

How far in advance should I book a flight from Santa Rosa to Chicago?

Find a great deal and save up to 95% by booking at least 35 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Santa Rosa to Chicago within the next two weeks, with the cheapest ticket starting at $397.

What is the cheapest month to fly from Santa Rosa to Chicago?

The best pricing can be found in the month of February. Prices to Chicago from Santa Rosa average $339. You can even find prices in February for less than $339, as users have found deals to Chicago from as low as $183. The month of December appears to be one of the more expensive times to travel to Chicago from Santa Rosa. Flying in the targeted month can save you up to 27%.

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.

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.

$159+ Flights from Santa Rosa to Chicago

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Cheap flight deals from Santa Rosa to Chicago

Round-trip from	$272 (Alaska Airlines)
One-way from	$159 (Alaska Airlines)
Popular in	February
Cheapest in	December
Average price	$361

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. 19% potential increase in price ($125 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).

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Average for round-trip flights in August 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 August 2, 2025.

Tue 10/219:43 amSTS - ORD

2 stops12h 16mAlaska Airlines

Wed 10/299:20 amORD - STS

1 stop7h 04mAlaska Airlines

Deal found 8/1

$272

Sat 8/302:28 pmSTS - ORD

1 stop7h 31mHawaiian Airlines

Sat 9/68:00 amORD - STS

1 stop7h 36mHawaiian Airlines

Deal found 8/1

$305

Best flights from Santa Rosa to Chicago
Discover carefully curated flight deals from Santa Rosa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2025.

Tue 10/219:43 amSTS - ORD

2 stops12h 16mAlaska Airlines

Wed 10/299:20 amORD - STS

1 stop7h 04mAlaska Airlines

Deal found 8/1

$272

Sat 8/302:28 pmSTS - ORD

1 stop7h 31mHawaiian Airlines

Sat 9/68:00 amORD - STS

1 stop7h 36mHawaiian Airlines

Deal found 8/1

$305

Last-minute flights from Santa Rosa to Chicago
Discover last-minute flight deals from Santa Rosa to Chicago. Data last updated August 2, 2025 and is based on user searches.

Thu 8/712:59 pmSTS - ORD

1 stop9h 36mAmerican Airlines

Thu 8/149:55 amORD - STS

1 stop7h 52mAmerican Airlines

Deal found 7/31

$829

Tue 8/127:12 amSTS - ORD

1 stop7h 45mAlaska Airlines

Thu 8/218:00 amORD - STS

1 stop7h 36mAlaska Airlines

Deal found 7/31

$780

Fri 8/1512:59 pmSTS - ORD

1 stop7h 44mAmerican Airlines

Sun 8/179:55 amORD - STS

1 stop7h 52mAmerican Airlines

Deal found 7/31

$759

Fri 8/225:55 pmSTS - ORD

1 stop9h 05mAlaska Airlines

Tue 8/268:00 amORD - STS

1 stop7h 41mAlaska Airlines

Deal found 7/31

$316

Sat 8/302:28 pmSTS - ORD

1 stop7h 31mHawaiian Airlines

Sat 9/68:00 amORD - STS

1 stop7h 36mHawaiian Airlines

Deal found 8/1

$305

One-way flights from Santa Rosa to Chicago
Search for one-way flight options from Santa Rosa to Chicago. Find affordable one-way fares based on user searches. Data last updated August 2, 2025.

Tue 9/162:28 pmSTS - ORD

1 stop7h 35mAlaska Airlines

Deal found 8/1

$159

Fly from

Fly to

Route

Depart

Return

Price

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 10/21

9:43 am-11:59 pm

2 stops12h 16m

Chicago O'Hare Intl

Wed 10/29

9:20 am-2:24 pm

1 stop7h 04m

$272

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Sat 8/30

2:28 pm-11:59 pm

1 stop7h 31m

Chicago O'Hare Intl

Sat 9/6

8:00 am-1:36 pm

1 stop7h 36m

$305

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Tue 9/16

2:28 pm-12:03 am

1 stop7h 35m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

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?

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

See what other customers who have flown with Alaska Airlines and Hawaiian 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

10,000 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Alaska Airlines

8.0

Very good

10,000 reviews

Alaska Airlines

8.0

Very good

10,000 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Hawaiian Airlines

7.8

Good

2,611 reviews

Alaska Airlines

8.0

Very good

10,000 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

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 $272, 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 Hawaiian Airlines for as low as $305. You may be able to fly from Santa Rosa to Chicago for 48% 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.

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Top 2 airlines flying from Santa Rosa to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Alaska Airlines	Cheapest$308	Average$582	FlexibilityNo cancel fee	On-time75%
American Airlines	Cheapest$318	Average$578	FlexibilityNo cancel fee	On-time71%

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$159+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Santa Rosa to Chicago with Cheapflights

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2. Select your favorite providers

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Cheap flight deals from Santa Rosa to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Santa Rosa to Chicago

Cheapest flights from Santa Rosa to ChicagoExplore 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 August 2, 2025.

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 August 2, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Santa Rosa to Chicago that are best for you.

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.

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?

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 August 2, 2025.

Reviews of airlines servicing Chicago

See what other customers who have flown with Alaska Airlines and Hawaiian 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.

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?

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

Can I find deals for flights from Santa Rosa to Chicago that include hotel bookings?

How can I find direct flights from Santa Rosa to Chicago?

Can I find deals for business class flights from Santa Rosa to Chicago?

What is the cheapest month to book a flight from Santa Rosa to Chicago?

Traveling to a place near Chicago?

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Alternative routes for Santa Rosa to Chicago

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Top 2 airlines flying from Santa Rosa to Chicago

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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 August 2, 2025.