STS - ORD

$144 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 11/8. 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 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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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

Wed, Nov 5 - Mon, Nov 10
Alaska Airlines Logo
6:49 am - 7:55 pmSTS-ORD
11h 06m1 stop
Alaska Airlines Logo
2:54 pm - 11:57 pmORD-STS
11h 03m1 stop
$277Alaska Airlines
Find Deal
Tue, Oct 21 - Wed, Nov 5
Alaska Airlines Logo
9:43 am - 11:59 pmSTS-ORD
12h 16m2 stops
Alaska Airlines Logo
9:20 am - 4:02 pmORD-STS
8h 42m1 stop
$283Alaska Airlines
Find Deal
Thu, Nov 13 - Tue, Nov 18
Alaska Airlines Logo
6:49 am - 7:55 pmSTS-ORD
11h 06m1 stop
Alaska Airlines Logo
9:20 am - 4:02 pmORD-STS
8h 42m1 stop
$288Alaska Airlines
Find Deal
Tue, Oct 28 - Sat, Nov 15
Alaska Airlines Logo
10:50 am - 11:59 pmSTS-ORD
11h 09m2 stops
Alaska Airlines Logo
9:20 am - 9:46 pmORD-STS
14h 26m2 stops
$289Alaska Airlines
Find Deal
Mon, Nov 10 - Wed, Nov 12
Alaska Airlines Logo
7:46 pm - 1:54 pmSTS-ORD
16h 08m1 stop
Alaska Airlines Logo
9:20 am - 4:02 pmORD-STS
8h 42m1 stop
$297Alaska Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
Alaska Airlines Logo
6:49 am - 7:55 pmSTS-ORD
11h 06m1 stop
Alaska Airlines Logo
9:20 am - 11:57 pmORD-STS
16h 37m1 stop
$298Alaska Airlines
Find Deal
Tue, Oct 28 - Wed, Nov 19
Alaska Airlines Logo
10:50 am - 11:59 pmSTS-ORD
11h 09m2 stops
Alaska Airlines Logo
9:20 am - 11:57 pmORD-STS
16h 37m1 stop
$304Alaska Airlines
Find Deal
Sat, Oct 18 - Fri, Oct 24
Alaska Airlines Logo
6:25 am - 11:59 pmSTS-ORD
15h 34m1 stop
Alaska Airlines Logo
3:50 pm - 11:16 pmORD-STS
9h 26m1 stop
$307Alaska Airlines
Find Deal
Wed, Nov 5 - Mon, Nov 10
Alaska Airlines Logo
6:49 am - 12:24 amSTS-ORD
15h 35m2 stops
Alaska Airlines Logo
2:54 pm - 11:57 pmORD-STS
11h 03m1 stop
$311Alaska Airlines
Find Deal
Fri, Nov 14 - Tue, Nov 18
Alaska Airlines Logo
7:46 pm - 7:55 pmSTS-ORD
22h 09m1 stop
Alaska Airlines Logo
9:20 am - 4:02 pmORD-STS
8h 42m1 stop
$317Alaska Airlines
Find Deal

Everything you should know

When to travel
November
Cheapest • 43% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$277
Overall average: $308
Alaska Airlines
Wed 11/5Mon 11/10
STS - ORD • 1 stop
Cheapest one-way
$144
Alaska Airlines
Sat 11/8
STS - ORD • 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 Chicago!
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’s the cheapest day of the week to fly from Santa Rosa to Chicago?

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

Your flight ticket price will generally be cheaper if you fly to Chicago on a Wednesday and more expensive on a Thursday. On your return trip to Santa Rosa, you should consider flying back on a Tuesday, and avoid Wednesdays for better deals.

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 $308 (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$144
Best time to beat the crowds but there is an average 91% increase in price.
Most popular time to fly and prices are also 25% 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 $144 for a one-way ticket and $277 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 $542 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 $653 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 10000 reviews
8.1Boarding
8.5Crew
7.1Food
7.8Comfort
7.1Entertainment
Airline reviews

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

10.0 ExcellentAnonymous, Sep 2025ONT - PDX
Read more Alaska Airlines reviews

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

Flight attendant was awful, I felt second hand embarrassment with every one of her interactions with people onboard. She was so incredibly rude every chance she got

Great flight - efficient and cheerful team on board, at SFO gate. Also, PAE (Paine Field, Everett, WA) is a great little airport to fly out or in to!

Why was I charged for a glass of wine on one flight and not on another? Why no movie or TVs? It was a long flight.

My flight wait is 3 hours delayed due to Unknown reason. We waited a very long time in the tarmac. Our flight 24 was scheduled @ 7, therefore we left my house at 330 to park our car. We were at the gate @ 530, then we were told at 6a that it will be late , we boarded at 930 but did not take off until 1015. Therefore my arranged pick up in JFK was cancelled because of no show. Before all these I got an email offers of changing my flight to a different date which I took a day earlier. I will never again take Alaska Airlines, very Inefficient and Disappointing.

Such great crew, from checkin to the plane. So friendly and helpful, I was genuinely impressed.

I was sitting towards back of plane and the flight attendants I thought spoke unusually loud for an evening flight. They chatted and chatted all night long and it seemed odd to me that they didn’t try to lower their voices. It is annoying as a passenger to hear all their conversations.

5 1/2 hour trip. Nice plane. easy boarding. Could have used a bit more beverage service but it was a red eye flight and they didn't want to wake everyone.

Staff at Gate desk were helpful. My connecting flight from the first part of my trip Kona to Seattle was late. I had to run through SeaTac Seattle to catch my flight to San Jose. They made an exception to let me board. On my return trip San Jose to San Diego and San Diego to Honolulu the same thing happened. One flight arrived late and I had to run through the terminal to catch my connection. There are no Gluten-free & Vegan options meals and snacks to purchase.

Had to pay $8 for internet wasnt cool, no tv’s, had to use phone to watch movies, no food choices seemed available unless u ordered in advance maybe I'm wrong about that but seemed that way, no snacks were served. Seemed a very bare bones flight. But it was on time and safe so that was good

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

Information on your arrival and departure airports

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