STS - ORD

$137 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 9/23. 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

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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Flights 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

Fri, Nov 14 - Tue, Nov 18
Alaska Airlines Logo
2:29 pm - 6:22 amSTS-ORD
13h 53m1 stop
Alaska Airlines Logo
8:00 am - 1:37 pmORD-STS
7h 37m1 stop
$292Alaska Airlines
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Tue, Sep 30 - Fri, Oct 3
Alaska Airlines Logo
2:28 pm - 11:59 pmSTS-ORD
7h 31m1 stop
Alaska Airlines Logo
5:45 pm - 1:34 pmORD-STS
21h 49m1 stop
$298Alaska Airlines
Find Deal
Fri, Nov 14 - Tue, Nov 18
Alaska Airlines Logo
7:35 pm - 9:39 pmSTS-ORD
24h 04m2 stops
Alaska Airlines Logo
8:00 am - 5:45 pmORD-STS
11h 45m2 stops
$303Alaska Airlines
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Tue, Sep 30 - Fri, Oct 3
Alaska Airlines Logo
7:00 am - 10:04 pmSTS-ORD
13h 04m1 stop
Alaska Airlines Logo
6:20 am - 11:59 pmORD-STS
19h 39m2 stops
$314Alaska Airlines
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Fri, Aug 15 - Mon, Aug 18
Alaska Airlines Logo
6:47 pm - 11:39 pmSTS-ORD
26h 52m1 stop
Alaska Airlines Logo
8:42 pm - 7:07 pmORD-STS
24h 25m1 stop
$329Alaska Airlines
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Tue, Jul 1 - Sat, Jul 5
American Airlines Logo
4:16 pm - 12:32 amSTS-ORD
6h 16m1 stop
American Airlines Logo
7:22 am - 12:31 pmORD-STS
7h 09m1 stop
$489American Airlines
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Sun, Aug 3 - Sat, Aug 9
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
$499Hawaiian Airlines
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Sat, Jul 12 - Mon, Jul 14
Hawaiian Airlines Logo
11:55 am - 11:39 pmSTS-ORD
9h 44m1 stop
Hawaiian Airlines Logo
6:00 am - 1:25 pmORD-STS
9h 25m1 stop
$644Hawaiian Airlines
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Thu, Jul 3 - Mon, Jul 7
American Airlines Logo
4:17 pm - 12:32 amSTS-ORD
6h 15m1 stop
American Airlines Logo
6:00 am - 11:40 amORD-STS
7h 40m1 stop
$759American Airlines
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Mon, Jul 7 - Sun, Jul 13
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
$802Hawaiian Airlines
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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$137
Best time to beat the crowds but there is an average 74% increase in price.
Most popular time to fly with an average 20% 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 $137 for a one-way ticket and $292 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 $629 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 $568 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
7.1Food
8.1Boarding
7.1Entertainment
7.8Comfort
8.5Crew
Airline reviews

Very bad, terrible food and late by 2 hours. Then no to open aircraft doors

2.0 MediocreStephen, Jun 2025SAN - HNL
Read more Alaska Airlines reviews

Very bad, terrible food and late by 2 hours. Then no to open aircraft doors

The Alaska app and website were not fully operational. I had to spend about 15 minutes at the counter doing things that should have been completed online. The agent was very nice and helpful, however.

Flying on Hawaiian Airlines was good. But, getting a boarding pass was a hassle. I booked what I thought was an Alaska Airlines flight that was actually a Hawaiian Airlines flight. I couldn't check in online. I had to wait for the Hawaiian Airlines counter to open so I could get my boarding pass which was a requirement for me to get in The Club or the Centurion Lounge. (I had no check in luggage so I didn't expect to have to physically check in.) The Alaska Airlines staff blamed the FAA for the problem.

Staff are helpful and patient. I don’t appreciate the almost 5 hours delay and also the delay of our luggage and being switched from one carousel to another to pick them up.

Staff were great but we were delayed on the tarmac for over an hour.

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

Thank you still providing bags for vomit. My son had a migraine and needed a bag to vomit in and it was right there behind the seat in front of us. Thank you!

We waited over an hour for our luggage to arrive at the carousel in Seattle.

The plane was delayed a bit. It wasn't a huge problem though, as we were heading back home.

Flight was great. Boarding was crazy because another flight was boarding late next to ours so everyone was standing and in the way.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

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?

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

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