STS - ORD

$182 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 5/30. 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

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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Cheap Flights from Santa Rosa to Chicago

 
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.

Recent round-trip flight deals from Santa Rosa to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Santa Rosa to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Alaska Airlines Logo
6:58 pm - 11:56 pmSTS-ORD
26h 58m1 stop
Alaska Airlines Logo
6:00 am - 1:25 pmORD-STS
9h 25m1 stop
$322Alaska Airlines
Find Deal
Wed, May 28 - Tue, Jun 3
Alaska Airlines Logo
9:38 am - 11:56 pmSTS-ORD
12h 18m2 stops
Alaska Airlines Logo
6:00 am - 1:25 pmORD-STS
9h 25m1 stop
$327Alaska Airlines
Find Deal
Wed, May 28 - Tue, Jun 3
Alaska Airlines Logo
9:38 am - 11:56 pmSTS-ORD
12h 18m2 stops
Alaska Airlines Logo
6:00 am - 6:18 pmORD-STS
14h 18m2 stops
$340Alaska Airlines
Find Deal
Wed, May 28 - Tue, Jun 3
Alaska Airlines Logo
7:00 am - 11:56 pmSTS-ORD
14h 56m2 stops
Alaska Airlines Logo
6:00 am - 1:25 pmORD-STS
9h 25m1 stop
$389Alaska Airlines
Find Deal
Thu, Jun 5 - Sun, Jun 8
Alaska Airlines Logo
7:00 am - 10:30 pmSTS-ORD
13h 30m2 stops
Alaska Airlines Logo
7:00 am - 6:07 pmORD-STS
13h 07m2 stops
$402Alaska Airlines
Find Deal
Tue, Jul 22 - Tue, Aug 12
Alaska Airlines Logo
8:01 pm - 5:40 amSTS-ORD
7h 39m1 stop
Alaska Airlines Logo
6:00 am - 7:07 pmORD-STS
15h 07m1 stop
$409Alaska Airlines
Find Deal
Mon, Jun 16 - Wed, Jun 18
Alaska Airlines Logo
7:00 am - 10:30 pmSTS-ORD
13h 30m2 stops
Alaska Airlines Logo
8:00 am - 7:07 pmORD-STS
13h 07m1 stop
$411Alaska Airlines
Find Deal
Tue, Jul 22 - Sat, Aug 16
Hawaiian Airlines Logo
8:01 pm - 5:40 amSTS-ORD
7h 39m1 stop
Hawaiian Airlines Logo
6:00 am - 1:25 pmORD-STS
9h 25m1 stop
$412Hawaiian Airlines
Find Deal
Thu, Jun 5 - Sun, Jun 8
Hawaiian Airlines Logo
8:01 pm - 5:40 amSTS-ORD
7h 39m1 stop
Hawaiian Airlines Logo
1:03 pm - 7:07 pmORD-STS
8h 04m1 stop
$576Hawaiian Airlines
Find Deal
Thu, Jun 12 - Sun, Jun 15
American Airlines Logo
12:24 pm - 9:08 pmSTS-ORD
6h 44m1 stop
American Airlines Logo
6:00 am - 11:44 amORD-STS
7h 44m1 stop
$759American Airlines
Find Deal
Wed, May 14 - Sun, May 18
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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 December, where tickets cost $333 (return) on average. On the other hand, the most expensive months are January and November, where the average cost of round-trip tickets is $1,028 and $853 respectively.

Good to know

Low seasonJanuary
High seasonApril
Cheapest flight$182
Best time to beat the crowds but there is an average 69% increase in price.
Most popular time to fly with an average 16% increase in price.
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 $182 for a one-way ticket and $322 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 $637 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 $578 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.

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 9968 reviews
8.2Boarding
7.9Comfort
7.1Food
7.1Entertainment
8.5Crew
Airline reviews

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

2.0 MediocreAnonymous, Apr 2025SNA - PDX
Read more Alaska Airlines reviews

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

There was no seating at the gate, no where to charge your devices, super crowded. Boarding in group F meant all luggage space was taken when it was time for me to board. The boarding crew was short with everyone and seemed irritated. The luggage space was insufficient, the seat was too small for me (6'4") and very uncomfortable trip. I was in a middle seat between a person snoring the whole trip and a person with very strong body odor. The flight crew was terse and unfriendly, seemed irritated and impatient. Yelled a lot at people with earbuds in, understandable. Finally, we arrived 10 minutes early, only to sit on the tarmac for 20 minutes and wait for a gate. Worst flight experience I've had in years.

Check your emails that you sent me. 9 emails were sent telling me that my flight is Delayed. Each one with a different time 7:10, 7:55, 9:31, 9:09, 9:29, 9:44, 10:00, 9:49, and 10:10. That was how my experience went.

It was my first time flying Alaska Airlines and first time flying from Santa Rosa airport. The staff was very professional and friendly. Their instructions were clear and any question was answered satisfactorily. My seat was comfortable and the in-flight beverage service very adequate for the duration of the flight. We arrived ahead of the scheduled landing time and deplaning was simple. I look forward to flying with Alaska again.

Personal demeanor not good on flight returning to LAX..Great and superb on the way to Portland

No non-alcoholic drinks available except water and small apple juice cans.

Flight attendant took my carefully folded coat and flung it across the aisle to the bin across the way. Where one of the passengers rescued it for me, because that just wasn’t right!!

First time flying with any airline that has decent seating. Great experience crew was friendly and the pilot was as well.

The flight was delayed by 3 hours and 30 minutes without any explanation.

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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

Information on your arrival and departure airports

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