Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

STS - ORD

Find cheap flights from Santa Rosa to Chicago from $383

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Santa Rosa to Chicago departing on 5/31. 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
0 bags
Wed 5/29
Wed 6/5

Search hundreds of travel sites at once for deals on flights to Chicago

 
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
In the last 7 days travelers have searched 43,983,279 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
7:28 pm - 1:54 pmSTS-ORD
16h 26m1 stop
6:00 am - 10:34 pmORD-STS
18h 34m1 stop
$383Alaska Airlines
Find Deal
Fri, May 31 - Tue, Jun 4
7:28 pm - 4:40 amSTS-ORD
7h 12m1 stop
7:29 pm - 11:16 amORD-STS
17h 47m2 stops
$448Alaska Airlines
Find Deal
Fri, May 31 - Tue, Jun 4
7:00 am - 5:30 amSTS-ORD
20h 30m2 stops
7:00 am - 9:53 pmORD-STS
16h 53m2 stops
$484Alaska Airlines
Find Deal
Sat, Oct 19 - Tue, Oct 22
2:18 pm - 5:40 amSTS-ORD
13h 22m1 stop
9:20 pm - 10:34 pmORD-STS
27h 14m1 stop
$488Alaska Airlines
Find Deal
Tue, May 21 - Fri, May 24
11:56 am - 5:40 amSTS-ORD
15h 44m2 stops
9:20 pm - 10:34 pmORD-STS
27h 14m1 stop
$493Alaska Airlines
Find Deal
Tue, May 21 - Fri, May 24
11:56 am - 5:40 amSTS-ORD
15h 44m2 stops
9:20 pm - 11:16 amORD-STS
15h 56m2 stops
$498Alaska Airlines
Find Deal
Tue, May 21 - Fri, May 24
12:27 pm - 11:34 pmSTS-ORD
9h 07m1 stop
5:30 am - 3:42 pmORD-STS
12h 12m2 stops
$501American Airlines
Find Deal
Tue, Aug 27 - Wed, Sep 4
2:36 pm - 5:30 amSTS-ORD
12h 54m2 stops
9:10 pm - 10:07 pmORD-STS
26h 57m1 stop
$509Alaska Airlines
Find Deal
Fri, Aug 23 - Sun, Aug 25
10:01 am - 5:30 amSTS-ORD
17h 29m1 stop
7:00 am - 9:21 amORD-STS
28h 21m1 stop
$512Alaska Airlines
Find Deal
Sat, Oct 19 - Tue, Oct 22
4:15 pm - 7:57 amSTS-ORD
13h 42m2 stops
5:30 am - 3:42 pmORD-STS
12h 12m2 stops
$530American Airlines
Find Deal
Tue, Aug 27 - Wed, Sep 4

Flights from Santa Rosa to Chicago - Travel Insights & Trends

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 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 Tuesday and more expensive on a Thursday. On your return trip to Santa Rosa, you should consider flying back on a Saturday, 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 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 February, where tickets cost $317 on average. On the other hand, the most expensive months are June and November, where the average cost of tickets is $498 and $466 respectively.

How far in advance should I book a flight from Santa Rosa to Chicago O'Hare Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Santa Rosa to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Santa Rosa to Chicago O'Hare Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 85 days before departure.

Good to know

Low season

March

High season

June

Cheapest flight

$383
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 46% 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 $383 for a round-trip ticket.

  • 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.

  • 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.

See more FAQs

Top airline 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.
7.3
American AirlinesOverall score based on 14834 reviews
7.2Comfort
8.0Crew
7.6Boarding
7.1Entertainment
6.6Food
Airline reviews

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

6.0 GoodAnonymous, Apr 2024SPI - ORD
Read more about American Airlines reviews

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Santa Rosa - Chicago Flights

Departure:

Santa Rosa (STS)United States

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Santa Rosa

Cabin classes:

Browse origins:

Browse destinations: