ORD - STS

$157 Find Cheap Flights from Chicago to Santa Rosa - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Santa Rosa departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Santa Rosa

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Santa Rosa, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Santa Rosa, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$346
Typical prices: $658-$547
Alaska Airlines
Tue 10/27Sat 10/31
ORD - STS • 1 stop
Cheapest one-way
$157
Alaska Airlines
Wed 8/19
ORD - STS • 1 stop
Top airlines
Cheapest • from $346 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Santa Rosa. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $525 (round-trip)
Shortest trip • 7h 16m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Santa Rosa!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Santa Rosa (ORD-STS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Santa Rosa that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Santa Rosa

Tue, Oct 27 - Sat, Oct 31
Alaska Airlines Logo
6:00 am - 1:06 pm
ORD
-
STS
9h 06m
1 stop
Alaska Airlines Logo
7:00 am - 6:20 pm
STS
-
ORD
9h 20m
1 stop
$346Alaska Airlines
Sat, Aug 22 - Tue, Aug 25
Alaska Airlines Logo
6:01 am - 2:12 pm
ORD
-
STS
10h 11m
1 stop
Alaska Airlines Logo
10:34 am - 7:21 pm
STS
-
ORD
6h 47m
1 stop
$357Alaska Airlines
Tue, Jul 14 - Tue, Jul 21
Alaska Airlines Logo
6:20 am - 5:16 pm
ORD
-
STS
12h 56m
2 stops
Alaska Airlines Logo
1:06 pm - 6:57 pm
STS
-
ORD
27h 51m
2 stops
$360Alaska Airlines
Fri, Aug 21 - Tue, Aug 25
Alaska Airlines Logo
2:18 pm - 9:54 am
ORD
-
STS
21h 36m
1 stop
Alaska Airlines Logo
10:34 am - 7:21 pm
STS
-
ORD
6h 47m
1 stop
$363Alaska Airlines
Tue, Oct 20 - Sat, Oct 24
Alaska Airlines Logo
2:21 pm - 4:12 pm
ORD
-
STS
27h 51m
2 stops
Alaska Airlines Logo
7:00 am - 6:20 pm
STS
-
ORD
9h 20m
1 stop
$372Alaska Airlines
Tue, Aug 18 - Thu, Aug 20
Alaska Airlines Logo
6:20 am - 5:16 pm
ORD
-
STS
12h 56m
2 stops
Alaska Airlines Logo
6:13 am - 11:59 pm
STS
-
ORD
15h 46m
1 stop
$374Alaska Airlines
Sat, Aug 8 - Mon, Aug 10
Alaska Airlines Logo
5:59 pm - 10:58 pm
ORD
-
STS
6h 59m
1 stop
Alaska Airlines Logo
5:56 pm - 1:21 pm
STS
-
ORD
17h 25m
1 stop
$379Alaska Airlines
Tue, Jul 28 - Tue, Aug 4
Alaska Airlines Logo
6:20 am - 5:16 pm
ORD
-
STS
12h 56m
2 stops
Alaska Airlines Logo
7:03 pm - 5:00 am
STS
-
ORD
7h 57m
1 stop
$380Alaska Airlines
Sat, Aug 8 - Mon, Aug 10
Alaska Airlines Logo
7:20 am - 4:55 pm
ORD
-
STS
11h 35m
2 stops
Alaska Airlines Logo
7:00 am - 5:00 am
STS
-
ORD
20h 00m
1 stop
$390Alaska Airlines
Tue, Oct 27 - Sat, Oct 31
Alaska Airlines Logo
6:00 am - 1:06 pm
ORD
-
STS
9h 06m
1 stop
Alaska Airlines Logo
7:00 am - 11:59 pm
STS
-
ORD
14h 59m
2 stops
$392Alaska Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Santa Rosa flights

Get data-powered insights and trends into flights from Chicago to Santa Rosa to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Santa Rosa?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Santa Rosa departing in October.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Santa Rosa?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Santa Rosa, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Santa Rosa is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are August and November, where the average cost of round-trip tickets is $878 and $769 respectively.

Good to know

Low seasonDecember
Cheapest flight$157
Best time to beat the crowds with an average 55% drop in price.
Most popular time to fly with an average 67% increase in price.
Flight from Chicago to Santa Rosa

When to book flights from Chicago to Santa Rosa

Are your dates flexible? Find out the best times to travel from Chicago to Santa Rosa based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Santa Rosa flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Santa Rosa?

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Santa Rosa was $157 for a one-way ticket and $346 for a round-trip.

  • Do I need a passport to fly between Chicago and Santa Rosa?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago to Santa Rosa?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Santa Rosa?

    oneworld is the only airline alliance operating flights between Chicago and Santa Rosa.

  • Which is the best airline for flights from Chicago to Santa Rosa, Alaska Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Santa Rosa are Alaska Airlines and American Airlines. With an average price for the route of $478 and an overall rating of 7.9, Alaska Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $743 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Santa Rosa?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Santa Rosa.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Santa Rosa?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Santa Rosa from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Santa Rosa?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Santa Rosa with an airline and back to Chicago with another airline. Booking your flights between Chicago and STS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Santa Rosa?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Santa Rosa from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Santa Rosa

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Santa Rosa. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Santa Rosa? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12508 reviews
8.1Boarding
8.5Crew
7.0Entertainment
7.0Food
7.8Comfort
Airline reviews

People were friendly. Flight was a little delayed. Maybe I missed the reason for it. Overall a nice experience.

8.0 ExcellentScott, Jun 2026
SEA - LAX
Read more Alaska Airlines reviews

People were friendly. Flight was a little delayed. Maybe I missed the reason for it. Overall a nice experience.

The flight itself was great. But we had to wait over an hour to deplane so I missed my train. Not the crews fault. They were wonderful!

Great trip. No complaints. Impressed with the crew’s response to various challenges pre-boarding.

Over all it was great. My original flight was canceled but they quickly rebooked me. I was frustrated because I had to cancel my entire plans for the day but all considered, not bad. The crew tried to keep us calm while we sat in the plane for was felt was an hour or so but they could use a bit of a script. The seats were comfortable and I would give it another try.

Wish there were more complimentary drinks available - only had water and apple juice. Also - no snacks were provided during the flight, but we were offered some items as we exited the plane.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

On this flight there wer only 25 people on board. So no one in 5 rows ahead of me and noone in 7 rows behind me. So very chill.

Thanks for all you do to keep us safe and on time!

Departing flight for our weekend trip was cancelled due to weather which meant our return flight was useless. The whole thing was difficult to get support through but Alaska did recover and was able to reimburse us for the flights yesterday. For some reason, Kayak was not kept in the loop, adding to the confusion.

You sent me an email saying boarding was at 9:29 and AA sent one that was 8:29 on Sunday morning. I had to call AA to get that it was indeed 8:29.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Everything you need to know for your flight from Chicago to Santa Rosa

Information on your arrival and departure airports