ORD - STS

$138 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 10/7. 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

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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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 14 - Tue, Oct 21
Alaska Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
Alaska Airlines Logo
7:53 pm - 2:50 pmSTS-ORD
16h 57m1 stop
$277Alaska Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Alaska Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
Alaska Airlines Logo
9:43 am - 11:59 pmSTS-ORD
12h 16m2 stops
$283Alaska Airlines
Find Deal
Tue, Oct 14 - Sat, Oct 18
Alaska Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
Alaska Airlines Logo
6:25 am - 11:59 pmSTS-ORD
15h 34m1 stop
$297Alaska Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Hawaiian Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
Hawaiian Airlines Logo
7:05 am - 5:03 pmSTS-ORD
7h 58m1 stop
$305Hawaiian Airlines
Find Deal
Tue, Oct 14 - Wed, Oct 15
Alaska Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
Alaska Airlines Logo
6:25 am - 11:59 pmSTS-ORD
15h 34m2 stops
$311Alaska Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Alaska Airlines Logo
3:05 pm - 11:08 pmORD-STS
10h 03m1 stop
Alaska Airlines Logo
6:43 pm - 6:54 pmSTS-ORD
22h 11m1 stop
$317Alaska Airlines
Find Deal
Wed, Oct 8 - Tue, Oct 14
Alaska Airlines Logo
6:00 am - 1:36 pmORD-STS
9h 36m1 stop
Alaska Airlines Logo
6:25 am - 6:59 pmSTS-ORD
10h 34m1 stop
$318Alaska Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Alaska Airlines Logo
3:05 pm - 11:08 pmORD-STS
10h 03m1 stop
Alaska Airlines Logo
8:03 pm - 4:55 pmSTS-ORD
18h 52m2 stops
$325Alaska Airlines
Find Deal
Fri, Oct 24 - Tue, Oct 28
Alaska Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
Alaska Airlines Logo
6:49 am - 6:59 pmSTS-ORD
10h 10m1 stop
$332Alaska Airlines
Find Deal
Wed, Oct 8 - Tue, Oct 14
Multiple Airlines Logo
7:15 am - 6:11 pmORD-STS
12h 56m2 stops
Multiple Airlines Logo
9:43 am - 11:53 pmSTS-ORD
36h 10m2 stops
$343Multiple Airlines
Find Deal

Everything you should know

Top airlines
Alaska Airlines
Cheapest • from $277 (round-trip)
Hawaiian Airlines
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$277
Alaska Airlines
Tue 10/14Tue 10/21
ORD - STS • 1 stop
Cheapest one-way
$138
Alaska Airlines
Tue 10/7
ORD - STS • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Santa Rosa!
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 seasonJuly
Cheapest flight$138
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 25% 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 $138 for a one-way ticket and $277 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 $743 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 2729 reviews
7.7Comfort
8.0Boarding
7.0Food
8.5Crew
7.1Entertainment
Airline reviews

First class ticket. They ran out of food and I sat hungry watching the others eat

2.0 MediocreAnonymous, Sep 2025SEA - OAK
Read more Hawaiian Airlines reviews

First class ticket. They ran out of food and I sat hungry watching the others eat

Everything was great except having to check in at Alaska. That was a surprise and took extra time and effort. Should have been explained somewhere maybe on the HA electronic ticket.

I accidentally made this purchase and they wouldn’t refund me even though I called immediately to cancel it.

You. Changed my AIRLINE, CONFIRMATION CODE, TERMINAL. AND GATE COMM N CATION. WAS POOR AND SUBOPTITMUM AND RIDICULOUS MY AIRLINE WAS HAWAIIN. ,THEN SUDDENLY. YOU SAY IT WAS ALASKA Give me a break,,Black is not White I could not check in over the phone...all I received was Error. And info from Hawaiian air agent saying tooooo many people were trying to check in causing the problem On the other hand I am alive

I like that you have eliminated plastic cups, bottles and straws. The crew was conscientious about separating the used paper cups from the trash. This change to paper is a great move and makes me want to choose Alaska when I fly.

Attendants seemed un-engaged and indifferent when asked for assistance.

Overall it was a good flight. The thing I most appreciated was that you eliminated plastic cups and water bottles and stir sticks and had paper cups, wood stir sticks and cans. Plus, I saw that the airline staff were actually keeping the used paper cups separate and unfolding the used cardboard meal boxes and keeping those items separate from the trash. Good for them! This makes me want to support Alaska Airlines and fly Alaska again. Thank for taking this step in working to reduce single use plastics! Kudos!

Ok but why they need to sell the ear buds?

Departure was two hours late! Better than four hours late on our first flight

My experience was pleasant. It was perfect. That is enough🥰💃💖

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!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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

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