ORD - STS

$142 Find Cheap Flights from Chicago to Santa Rosa

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 1/20. 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
$273
Alaska Airlines
Mon 1/12Tue 1/20
ORD - STS • 2 stops
Cheapest one-way
$142
Alaska Airlines
Tue 1/20
ORD - STS • 2 stops
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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

Mon, Jan 12 - Tue, Jan 20
Alaska Airlines Logo
8:00 am - 12:22 pm
ORD
-
STS
30h 22m2 stops
Alaska Airlines Logo
6:50 am - 11:50 pm
STS
-
ORD
15h 00m2 stops
$273Alaska Airlines
Sat, Feb 21 - Sat, Feb 28
Alaska Airlines Logo
8:20 am - 7:02 pm
ORD
-
STS
12h 42m1 stop
Alaska Airlines Logo
8:00 am - 11:56 pm
STS
-
ORD
13h 56m2 stops
$278Alaska Airlines
Sat, Feb 21 - Tue, Feb 24
Alaska Airlines Logo
8:20 am - 7:02 pm
ORD
-
STS
12h 42m1 stop
Alaska Airlines Logo
10:51 am - 11:59 pm
STS
-
ORD
11h 08m1 stop
$282Alaska Airlines
Thu, Feb 5 - Tue, Feb 10
Alaska Airlines Logo
3:44 pm - 11:11 pm
ORD
-
STS
9h 27m1 stop
Alaska Airlines Logo
6:50 am - 11:50 pm
STS
-
ORD
15h 00m2 stops
$287Alaska Airlines
Thu, Feb 19 - Thu, Feb 26
Alaska Airlines Logo
3:54 pm - 9:14 am
ORD
-
STS
19h 20m2 stops
Alaska Airlines Logo
5:27 pm - 2:11 pm
STS
-
ORD
18h 44m2 stops
$288Alaska Airlines
Thu, Feb 5 - Tue, Feb 10
Alaska Airlines Logo
9:00 am - 11:11 pm
ORD
-
STS
16h 11m1 stop
Alaska Airlines Logo
2:30 pm - 2:29 pm
STS
-
ORD
21h 59m1 stop
$291Alaska Airlines
Tue, Feb 17 - Tue, Feb 24
Alaska Airlines Logo
5:29 pm - 9:52 pm
ORD
-
STS
30h 23m1 stop
Alaska Airlines Logo
10:51 am - 11:59 pm
STS
-
ORD
11h 08m1 stop
$292Alaska Airlines
Sat, Feb 21 - Wed, Feb 25
Alaska Airlines Logo
8:20 am - 7:02 pm
ORD
-
STS
12h 42m1 stop
Alaska Airlines Logo
7:00 am - 12:01 pm
STS
-
ORD
27h 01m2 stops
$293Alaska Airlines
Wed, Mar 11 - Wed, Mar 18
Alaska Airlines Logo
7:40 am - 7:02 pm
ORD
-
STS
13h 22m1 stop
Alaska Airlines Logo
7:00 am - 7:02 pm
STS
-
ORD
10h 02m1 stop
$297Alaska Airlines
Thu, Feb 19 - Thu, Feb 26
Alaska Airlines Logo
7:00 am - 11:50 pm
ORD
-
STS
18h 50m1 stop
Alaska Airlines Logo
7:57 pm - 11:56 pm
STS
-
ORD
25h 59m1 stop
$302Alaska 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’s the cheapest day of the week to fly from Chicago to Santa Rosa?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Santa Rosa clicked on KAYAK for each day over the last 12 months.

For Chicago to Santa Rosa, Tuesday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Santa Rosa back to Chicago, the best deals are generally found on Wednesday, with Thursday being the most expensive.

Good to know

Low seasonDecember
Cheapest flight$142
Best time to beat the crowds with an average 62% drop in price.
Most popular time to fly with an average 30% 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 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Santa Rosa was $142 for a one-way ticket and $273 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, Hawaiian Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Santa Rosa are Hawaiian Airlines and American Airlines. With an average price for the route of $547 and an overall rating of 7.8, Hawaiian Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $783 and an overall rating of 7.2.

  • 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.
7.8
Hawaiian AirlinesOverall score based on 2820 reviews
8.5Crew
7.7Comfort
8.0Boarding
7.1Entertainment
6.9Food
Airline reviews

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

6.0 GoodGregg, Dec 2025
HNL - OAK
Read more Hawaiian Airlines reviews

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

I like Hawaiian, it was great that they had good internet connection across the Pacific Ocean, thanks to Star Link satellites. The seating was comfortable, ( I was in economy ). Maybe I missed it, but I only got offered a beverage once. It was a nonstop flight KOA to SMF. I would take it again next time I go that way.

Previously flown Hawaiian Airlines on similar routes, I found Alaska Airlines to be noticeably more comfortable. The seats on Alaska Airlines provided better support and cushioning, which made a significant difference on the long flight to the islands. When you’re spending 5-6 hours in the air, seat comfort really matters, and Alaska Airlines delivered where it counts. After comparing both carriers, I’ve decided to book with Alaska Airlines for all my future Hawaii trips. The superior seat comfort alone makes it worth choosing Alaska over Hawaiian Airlines. If you’re planning a trip to Hawaii and prioritizing comfort, I’d recommend giving Alaska Airlines a try. You won’t be disappointed. Highly recommended for Hawaii travel!

I received several emails about my 3:10 flight. When I showed up to the airport at 12:30 to check my bags I was told the flight was actually at 1 pm. They grudgingly rebooked me for a flight at 5:22 to Vegas to get a connecting to LAX. I did find the gate for my original 3:10 flight but they were booked. I proceeded to receive status updates and gate change information for the 3:10 flight, even though I was apparently never supposed to be on that flight

The crew was EXTREMELY helpful And sweet and the flight was smooth!

The Kayak confirmation number did not work for checking in the day before. I checked in at 8.30 using my ticket number. When I arrived at the airport, I was informed that the flight was overbooked, and since I had checked in late, I did not have a seat. The Next flight was not until ten PM. I called my wife, who had been taking care of our kids all weekend, and she was upset, calling me a liar and telling me to stay in SD. It turned my weekend getaway into a nightmare! I blame the Kayak website and will not book flights using your app in the future.

One hour waiting time after boarding, but arrived in time. I am satisfied

Flying with Hawaiian Airlines is a treat! They have the best crew, food and drinks! I’ve always enjoyed flying with Hawaiian Airlines and will continue to use them!

Amazing all female crew, including the pilot. Great flight attendants and smooth trip. Food was good. Boarding the plane from back to front would have made things significantly smoother. Took forever to wait for people to clear the alley. A little extra leg room would be nice also. Please thank your flight crew!

We decided to take our mom on vacation but we were worried how well she will do on the flight, she's a senior and required special accommodations such as transport chair since she can't stand for long periods. To our surprise my whole family was given priority boarding, my mom was given chair, we were not standing in line and were given seats in good area next to our mom. A+ experience!

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

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

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

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

Information on your arrival and departure airports