ORD - STS

$186 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 8/18. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$379
Typical prices: $513-$773
American Airlines
Sat 9/26Sat 10/3
ORD - STS • 1 stop
Cheapest one-way
$186
Alaska Airlines
Tue 8/18
ORD - STS • 2 stops
Top airlines
Cheapest • from $379 (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 09m (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

Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
5:00 am - 12:26 pm
ORD
-
STS
9h 26m
1 stop
American Airlines Logo
12:56 pm - 11:43 pm
STS
-
ORD
8h 47m
1 stop
$379American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
10:30 am - 3:37 pm
ORD
-
STS
7h 07m
1 stop
American Airlines Logo
12:58 pm - 11:30 pm
STS
-
ORD
8h 32m
1 stop
$380American Airlines
Tue, Nov 3 - Sat, Nov 14
Delta Logo
7:10 am - 4:08 pm
ORD
-
STS
10h 58m
2 stops
Delta Logo
11:25 am - 9:53 pm
STS
-
ORD
8h 28m
1 stop
$384Delta
Tue, Nov 3 - Sat, Nov 14
Delta Logo
8:15 am - 4:08 pm
ORD
-
STS
9h 53m
2 stops
Delta Logo
11:25 am - 11:50 pm
STS
-
ORD
10h 25m
2 stops
$389Delta
Tue, Aug 25 - Mon, Aug 31
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
$394Alaska Airlines
Sat, Oct 17 - Wed, Oct 21
Alaska Airlines Logo
7:16 pm - 1:06 pm
ORD
-
STS
19h 50m
1 stop
Alaska Airlines Logo
1:58 pm - 6:20 am
STS
-
ORD
14h 22m
2 stops
$398Alaska Airlines
Thu, Aug 27 - Sun, Aug 30
Alaska Airlines Logo
8:17 pm - 9:54 am
ORD
-
STS
15h 37m
1 stop
Alaska Airlines Logo
6:47 pm - 1:22 pm
STS
-
ORD
16h 35m
1 stop
$399Alaska Airlines
Sat, Aug 1 - Tue, Aug 4
Alaska Airlines Logo
5:59 pm - 10:58 pm
ORD
-
STS
6h 59m
1 stop
Alaska Airlines Logo
7:03 pm - 5:00 am
STS
-
ORD
7h 57m
1 stop
$401Alaska Airlines
Sat, Aug 8 - Sat, Aug 15
American Airlines Logo
6:00 am - 12:09 pm
ORD
-
STS
8h 09m
1 stop
American Airlines Logo
12:58 pm - 10:30 pm
STS
-
ORD
7h 32m
1 stop
$402American Airlines
Mon, Aug 24 - Tue, Sep 1
Alaska Airlines Logo
8:17 pm - 9:54 am
ORD
-
STS
15h 37m
1 stop
Alaska Airlines Logo
10:34 am - 7:21 pm
STS
-
ORD
6h 47m
1 stop
$406Alaska 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.

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 November and July, where the average cost of round-trip tickets is $885 and $764 respectively.

Good to know

Low seasonDecember
Cheapest flight$186
Best time to beat the crowds with an average 56% drop in price.
Most popular time to fly and prices are also 12% lower on average.
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 $186 for a one-way ticket and $379 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 $563 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 12590 reviews
7.0Food
8.5Crew
7.8Comfort
7.0Entertainment
8.1Boarding
Airline reviews

We showed up to our gate less than 15 minutes after boarding started and they wouldn’t let us in. It was still 15 minutes even before take off so we’re weren’t even late to the flight.

4.0 OkayAnonymous, Jun 2026
PDX - STS
Read more Alaska Airlines reviews

We showed up to our gate less than 15 minutes after boarding started and they wouldn’t let us in. It was still 15 minutes even before take off so we’re weren’t even late to the flight.

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

My flight got canceled never left san diego and miss out my fam event

would have been nice for flight to not be delayed by 2 hours so that we had to pay $80 to get home since BART had shut down. i thought a 10pm arrival would leave enough time to account for delays but i was wrong.

I like that volunteers were asked to check in their carryons for free. And then they come out of the carousels within 20 minutes as promised.

The landing was a little rough - but a good flight overall! :)

The issue was not alaska airlines. The ticket you printed was innacurate.

Pretty terrible. The aisles on this flight were too narrow so we had to carry our baby, care seat, luggage, travel stroller step by step down the aisle slowing down a lot of passengers in the process. Not only was this a safety hazard but remember that scene from game of thrones where Cersei walks naked through the streets? It felt about as excruciating as that except both me and my husband were carrying 50lbs of weight while everyone from the flight attendants and passengers dolled out comments like “that stroller doesn’t fit in the overhead compartment and you should check it at the gate” when it is a travel stroller that absolutely fits and did fit in the overhead compartment. The flight said it was 30 min delayed but in actuality we did not take off until 1.5 hours past the original time. It was absolutely terrible. Alaska also charged us 200 dollars just in baggage fees even tho we took the time to buy two check on baggages via their app and bought an extra seat for our child and they still refused to overlook our first time flying with them. Everyone in general looked super miserable and traveling with them with a child is pretty much untenable. Lastly I originally thought I had booked an AM flight for my family but it was a PM flight which I knew was not going to end well since we had a 1.5 year old with us on a flight that gets in 9p. I ended up calling Alaska to try to change the first leg for a change fee, and would even have accepted half of a refund to book a completely different flight but of course they refused and absolutely allowed no flexibility to plans so I guess my revenge was our baby cried for 3 out of the four hour flight and hopefully convinced every miserable person on that flight to never fly Alaska again 🤷🏻‍♀️

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

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.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Boarding was a mess - the agent basically called every group in rapid succession, so there was no organization at all. The economy seats are a joke, and main cabin extra seats were sold out when I purchased my flight. As such, I was locked in the same position for four hours. Being 6’6”, it was impossible to get my bag out from under the seat in front of me, and I couldn’t have used my laptop even if my bag were accessible due to the minuscule seat pitch. Also the wifi was broken. American is a joke - can’t wait until they merge with Spirit.

Horrible scam. Make you pay extra for more leg room then switch your seat as you’re boarding to a regular seat. Never fly American!

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

Information on your arrival and departure airports