ORD - STS

$133 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 4/15. 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
$265
Alaska Airlines
Tue 4/14Wed 4/29
ORD - STS • 1 stop
Cheapest one-way
$133
Alaska Airlines
Wed 4/15
ORD - STS • 1 stop
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 $333 (round-trip)
Shortest trip • 7h 17m (one-way)
Insights
Insights
Insights
Insights
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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!
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, Apr 14 - Wed, Apr 29
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
Alaska Airlines Logo
7:23 am - 7:03 pm
STS
-
ORD
9h 40m
1 stop
$265Alaska Airlines
Tue, Apr 14 - Thu, Apr 30
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
Alaska Airlines Logo
7:23 am - 11:43 pm
STS
-
ORD
14h 20m
1 stop
$272Alaska Airlines
Fri, Apr 17 - Wed, Apr 29
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
Alaska Airlines Logo
10:01 am - 7:03 pm
STS
-
ORD
7h 02m
1 stop
$285Alaska Airlines
Tue, May 5 - Wed, May 6
Alaska Airlines Logo
8:50 am - 7:06 pm
ORD
-
STS
12h 16m
1 stop
Alaska Airlines Logo
7:23 am - 7:03 pm
STS
-
ORD
9h 40m
1 stop
$289Alaska Airlines
Tue, Apr 14 - Sat, Apr 25
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
Alaska Airlines Logo
1:13 pm - 11:59 pm
STS
-
ORD
8h 46m
1 stop
$291Alaska Airlines
Fri, Apr 17 - Thu, Apr 30
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
Alaska Airlines Logo
7:23 am - 11:43 pm
STS
-
ORD
14h 20m
1 stop
$292Alaska Airlines
Fri, Apr 17 - Fri, May 1
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
Alaska Airlines Logo
7:23 am - 7:03 pm
STS
-
ORD
9h 40m
1 stop
$305Alaska Airlines
Mon, Apr 13 - Wed, Apr 29
Alaska Airlines Logo
7:59 pm - 10:03 am
ORD
-
STS
16h 04m
1 stop
Alaska Airlines Logo
7:23 am - 7:03 pm
STS
-
ORD
9h 40m
1 stop
$309Alaska Airlines
Fri, Apr 17 - Sat, Apr 25
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
Alaska Airlines Logo
1:13 pm - 11:59 pm
STS
-
ORD
8h 46m
1 stop
$311Alaska Airlines
Sat, Apr 18 - Mon, Apr 20
Alaska Airlines Logo
8:20 am - 7:05 pm
ORD
-
STS
12h 45m
1 stop
Alaska Airlines Logo
7:46 pm - 2:21 pm
STS
-
ORD
16h 35m
1 stop
$313Alaska 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 most popular layover airport when flying from Chicago to Santa Rosa?

Percentage of 1-stop round-trip flights from Chicago to Santa Rosa chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Phoenix (PHX) is the top choice – 61% of KAYAK users who clicked on 1-stop flights from Chicago to Santa Rosa picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago to Santa Rosa?

Average round-trip price for 1-stop flights from Chicago to Santa Rosa clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via San Diego (SAN) offer the most affordable fares, with an average round-trip price of $333.

Which layover airport offers the shortest total travel time from Chicago to Santa Rosa?

Shortest average total travel time for 1-stop one-way flights from Chicago to Santa Rosa via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Phoenix (PHX) for the shortest journey. The average one-way travel time for flights connecting there is 7h 17m.

Which layover airport has the quickest connection when flying from Chicago to Santa Rosa?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago to Santa Rosa, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Phoenix (PHX) often has the shortest layovers from Chicago to Santa Rosa, with an average of 1h 02m.

Good to know

Low seasonDecember
Cheapest flight$133
Best time to beat the crowds with an average 57% drop in price.
Most popular time to fly with an average 43% 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 $133 for a one-way ticket and $265 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 $749 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.
7.8
Hawaiian AirlinesOverall score based on 2838 reviews
6.9Food
7.7Comfort
7.1Entertainment
8.5Crew
8.0Boarding
Airline reviews

I like that if they asked you to checked in a bag at the gate they give you priority to board

10.0 ExcellentGRACE, Feb 2026
SMF - SAN
Read more Hawaiian Airlines reviews

I like that if they asked you to checked in a bag at the gate they give you priority to board

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!

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

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

Information on your arrival and departure airports