STS - ORD

$112 Find Cheap Flights from Santa Rosa to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Santa Rosa to Chicago departing on 3/23. 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 Chicago O'Hare Intl Airport

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

Cheapest round-trip
$223
Overall average: $425
Alaska Airlines
Tue 5/12Tue 5/19
STS - ORD • 1 stop
Cheapest one-way
$112
Alaska Airlines
Mon 3/23
STS - ORD • 1 stop
When to travel
November
Cheapest • 40% price drop
September
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 Chicago!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Santa Rosa to Chicago 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 Santa Rosa to Chicago

Tue, May 12 - Tue, May 19
Alaska Airlines Logo
7:23 am - 7:03 pm
STS
-
ORD
9h 40m
1 stop
Alaska Airlines Logo
3:43 pm - 11:26 pm
ORD
-
STS
9h 43m
1 stop
$223Alaska Airlines
Tue, May 12 - Mon, May 18
Alaska Airlines Logo
10:01 am - 7:03 pm
STS
-
ORD
7h 02m
1 stop
Alaska Airlines Logo
7:59 pm - 11:26 pm
ORD
-
STS
29h 27m
1 stop
$283Alaska Airlines
Tue, May 12 - Tue, May 19
Alaska Airlines Logo
7:00 am - 6:40 am
STS
-
ORD
21h 40m
2 stops
Alaska Airlines Logo
3:43 pm - 11:26 pm
ORD
-
STS
9h 43m
1 stop
$288Alaska Airlines
Tue, Mar 10 - Wed, Mar 11
Alaska Airlines Logo
10:51 am - 11:59 pm
STS
-
ORD
11h 08m
1 stop
Alaska Airlines Logo
3:54 pm - 9:52 pm
ORD
-
STS
7h 58m
1 stop
$290Alaska Airlines
Wed, Mar 18 - Wed, Mar 25
Alaska Airlines Logo
9:50 am - 7:02 pm
STS
-
ORD
7h 12m
1 stop
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
$300Alaska Airlines
Mon, Mar 2 - Sat, Mar 7
Alaska Airlines Logo
6:37 pm - 2:58 pm
STS
-
ORD
18h 21m
1 stop
Alaska Airlines Logo
3:54 pm - 9:52 pm
ORD
-
STS
7h 58m
1 stop
$303Alaska Airlines
Wed, Mar 4 - Wed, Mar 11
Alaska Airlines Logo
8:00 am - 11:56 pm
STS
-
ORD
13h 56m
2 stops
Alaska Airlines Logo
3:54 pm - 9:52 pm
ORD
-
STS
7h 58m
1 stop
$305Alaska Airlines
Fri, May 15 - Wed, May 20
Alaska Airlines Logo
7:38 pm - 6:46 pm
STS
-
ORD
21h 08m
1 stop
Alaska Airlines Logo
3:43 pm - 11:26 pm
ORD
-
STS
9h 43m
1 stop
$313Alaska Airlines
Thu, Mar 5 - Wed, Mar 11
Alaska Airlines Logo
7:57 pm - 1:11 pm
STS
-
ORD
15h 14m
2 stops
Alaska Airlines Logo
3:54 pm - 9:52 pm
ORD
-
STS
7h 58m
1 stop
$315Alaska Airlines
Wed, Mar 4 - Tue, Mar 10
Alaska Airlines Logo
8:00 am - 11:56 pm
STS
-
ORD
13h 56m
2 stops
Alaska Airlines Logo
3:54 pm - 9:52 pm
ORD
-
STS
7h 58m
1 stop
$318Alaska Airlines
Booking Insights

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Santa Rosa to Chicago O'Hare Intl Airport, 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 Santa Rosa to Chicago O'Hare Intl Airport is November, where tickets cost $329 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $1,028 and $775 respectively.

Good to know

Low seasonJanuary
Cheapest flight$112
Best time to beat the crowds but there is an average 87% increase in price.
Most popular time to fly and prices are also 28% lower on average.
Flight from Santa Rosa to Chicago

When to book flights from Santa Rosa to Chicago

Are your dates flexible? Find out the best times to travel from Santa Rosa to Chicago 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 Santa Rosa to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Santa Rosa to Chicago O'Hare Intl Airport was $112 for a one-way ticket and $223 for a round-trip.

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

    No

  • Which airports will I be using when flying from Santa Rosa to Chicago?

    Santa Rosa airport is called Santa Rosa Sonoma County and the only airport in Chicago is Chicago O'Hare Intl.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Santa Rosa to Chicago are Alaska Airlines and American Airlines. With an average price for the route of $408 and an overall rating of 8.0, 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 7.2.

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

    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 Santa Rosa to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Santa Rosa 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 Santa Rosa to Chicago?

    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 Chicago with an airline and back to Santa Rosa with another airline. Booking your flights between Santa Rosa and ORD 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 Santa Rosa to Chicago?

    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 Chicago from Santa Rosa 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 Santa Rosa to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Santa Rosa to Chicago. 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 Santa Rosa to Chicago? 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.
8.0
Alaska AirlinesOverall score based on 11819 reviews
7.8Comfort
7.1Food
8.1Boarding
7.0Entertainment
8.5Crew
Airline reviews

Due to plane delays on both legs of my flight home, I had to be rerouted from Santa Rosa to Las Vegas on Skywest and then to DCA on American. SkyWest airlines sat on runway in Las Vegas for 20 minutes waiting for gate to clear. My boarding pass for American that I was given by Alaska was incomplete and the Las Vegas airport lacked signage and departure boards. I barely made my flight bc it was so confusing. American Airlines has a much better wireless connection. I’ll never fly Alaska again. It clearly has problems.

2.0 MediocreAnonymous, Jan 2026
STS - SAN
Read more Alaska Airlines reviews

Due to plane delays on both legs of my flight home, I had to be rerouted from Santa Rosa to Las Vegas on Skywest and then to DCA on American. SkyWest airlines sat on runway in Las Vegas for 20 minutes waiting for gate to clear. My boarding pass for American that I was given by Alaska was incomplete and the Las Vegas airport lacked signage and departure boards. I barely made my flight bc it was so confusing. American Airlines has a much better wireless connection. I’ll never fly Alaska again. It clearly has problems.

I paid for wifi and it never worked... it was miserable. I couldn't access my shared files to work on the plane, it didn't work on my phone. I paid for nothing but frustration and continual refreshing, hoping it would work

The stewardess are very nice and pleasant, Someone onboard had a medical attention, and they attended that person non-stop all throughout the flight, and yet, did not forget to serve and help other passengers.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

My TSA pre check was left Off my boarding pass which was a large inconvenience.

Again, very smooth and all of the Alaska folks were great. They continue to meet all my needs.

Overall it was fine, however one of my two checked bags did not arrive and I was told it was left in Palm Springs. I don't understand how one of the two bags made it through fine but the other got lost .

The Alaska Airlines app made it very difficult to find my boarding pass. It was very frustrating to use! The flight itself was flawless.

It wasn’t great. Your app is not user friendly unless you sign up for those points. It tries to force you and won’t show you flight/trip info until you sign up. You have to somehow get into get your boarding pass because your kiosks don’t offer boarding pass information only bag check. It was not helpful or user friendly. The app is useless unless you sign up for your rewards program. My daughters info was missing even though I checked us in we had to get out of security and go back to a ticket window the woman told us that it sometimes populates incorrectly so it didn’t have her information. It populated incorrect birth date. She said this is common. Luckily we were at Palm Springs and not JFK where leaving the giant security line would have been a much bigger problem. I will avoid your airline in the future if it’s possible. Also no food availability except dry snack boxes.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

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

Information on your arrival and departure airports