STS - ORD

$172 Find Cheap Flights from Santa Rosa to Chicago - Compare and Save

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 7/4. 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
$343
Alaska Airlines
Tue 6/30Sat 7/4
STS - ORD • 1 stop
Cheapest one-way
$172
Alaska Airlines
Sat 7/4
STS - ORD • 1 stop
Top airlines
Cheapest • from $343 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Santa Rosa and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $353 (round-trip)
Shortest trip • 6h 12m (one-way)
Insights
Insights
Insights
Insights
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, Jun 30 - Sat, Jul 4
Alaska Airlines Logo
7:03 pm - 5:00 am
STS
-
ORD
7h 57m
1 stop
Alaska Airlines Logo
5:59 pm - 10:58 pm
ORD
-
STS
6h 59m
1 stop
$343Alaska Airlines
Wed, Sep 9 - Tue, Sep 15
Alaska Airlines Logo
6:13 am - 7:21 pm
STS
-
ORD
11h 08m
1 stop
Alaska Airlines Logo
7:20 am - 4:39 pm
ORD
-
STS
11h 19m
2 stops
$359Alaska Airlines
Tue, Jun 30 - Tue, Jul 14
Alaska Airlines Logo
7:03 pm - 5:00 am
STS
-
ORD
7h 57m
1 stop
Alaska Airlines Logo
6:20 am - 5:16 pm
ORD
-
STS
12h 56m
2 stops
$363Alaska Airlines
Wed, Aug 19 - Wed, Aug 26
Alaska Airlines Logo
1:40 pm - 11:59 pm
STS
-
ORD
32h 19m
2 stops
Alaska Airlines Logo
6:01 am - 4:39 pm
ORD
-
STS
12h 38m
2 stops
$371Alaska Airlines
Tue, Jun 30 - Wed, Jul 15
Alaska Airlines Logo
7:03 pm - 5:00 am
STS
-
ORD
7h 57m
1 stop
Alaska Airlines Logo
6:00 am - 11:58 am
ORD
-
STS
7h 58m
1 stop
$372Alaska Airlines
Tue, Sep 1 - Wed, Sep 9
Alaska Airlines Logo
6:47 pm - 1:22 pm
STS
-
ORD
16h 35m
1 stop
Alaska Airlines Logo
7:20 am - 4:39 pm
ORD
-
STS
11h 19m
2 stops
$373Alaska Airlines
Mon, Sep 28 - Tue, Sep 29
Alaska Airlines Logo
6:13 am - 7:21 pm
STS
-
ORD
11h 08m
1 stop
Alaska Airlines Logo
7:20 am - 4:39 pm
ORD
-
STS
11h 19m
2 stops
$374Alaska Airlines
Wed, Sep 2 - Tue, Sep 8
Alaska Airlines Logo
6:13 am - 7:21 pm
STS
-
ORD
11h 08m
1 stop
Alaska Airlines Logo
7:20 am - 11:54 pm
ORD
-
STS
18h 34m
1 stop
$375Alaska Airlines
Tue, Nov 10 - Sat, Nov 14
Alaska Airlines Logo
6:56 pm - 11:49 pm
STS
-
ORD
26h 53m
1 stop
Alaska Airlines Logo
2:25 pm - 10:33 pm
ORD
-
STS
10h 08m
1 stop
$377Alaska Airlines
Wed, Aug 5 - Mon, Aug 10
Alaska Airlines Logo
1:06 pm - 11:36 pm
STS
-
ORD
32h 30m
2 stops
Alaska Airlines Logo
6:20 am - 5:16 pm
ORD
-
STS
12h 56m
2 stops
$378Alaska 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.

Which airlines provide the cheapest flights from Santa Rosa to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Santa Rosa to Chicago were found on Alaska Airlines ($343) and Delta ($384).

Good to know

Cheapest flight$172
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 5 days, the lowest price for a flight from Santa Rosa to Chicago O'Hare Intl Airport was $172 for a one-way ticket and $343 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.

  • 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 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.
7.9
Alaska AirlinesOverall score based on 12534 reviews
7.0Entertainment
8.1Boarding
7.8Comfort
8.5Crew
7.0Food
Airline reviews

Subject: Formal Complaint – Incompetent Service and Denied Boarding on Flight 1409 (CLSVJM – Dear Alaska Airlines Customer Relations, I am writing to file a formal complaint regarding my experience on Flight 1409 departing from Seattle on 6/13/26. As a physician and business owner who frequently coordinates group travel, this was one of the worst airline experiences I have encountered. Upon arrival, I was informed that my check-in boarding pass was not official, despite successfully obtaining it electronically through your website/app with no warnings or indications of issues. My electronic boarding pass was rejected, leading to cancellation/denial of boarding. The gate agent (an older woman) was unhelpful, claimed my name had been announced multiple times (which it had not—she did not even know my name correctly), and mistakenly boarded my traveling companion under my name. Additionally, an older blonde staff member nearly failed to return my passport, highlighting a clear lack of training on your check-in and boarding systems. This chaos forced me onto a later flight while my group waited in Canada, unable to check into our Airbnb or pick up rental cars (as I was the primary booker). The entire incident caused significant business disruption, stress, and additional expenses. I have flown Alaska Airlines previously but will not consider it again without resolution. I request: • Full reimbursement of any additional costs incurred. • Appropriate compensation (vouchers/miles) for the inconvenience and poor service. • Confirmation of corrective actions for Please respond within 7-10 business days. Sincerely, Dr. Chunwen Teng

2.0 MediocreJane, Jun 2026
SMF - SEA
Read more Alaska Airlines reviews

Subject: Formal Complaint – Incompetent Service and Denied Boarding on Flight 1409 (CLSVJM – Dear Alaska Airlines Customer Relations, I am writing to file a formal complaint regarding my experience on Flight 1409 departing from Seattle on 6/13/26. As a physician and business owner who frequently coordinates group travel, this was one of the worst airline experiences I have encountered. Upon arrival, I was informed that my check-in boarding pass was not official, despite successfully obtaining it electronically through your website/app with no warnings or indications of issues. My electronic boarding pass was rejected, leading to cancellation/denial of boarding. The gate agent (an older woman) was unhelpful, claimed my name had been announced multiple times (which it had not—she did not even know my name correctly), and mistakenly boarded my traveling companion under my name. Additionally, an older blonde staff member nearly failed to return my passport, highlighting a clear lack of training on your check-in and boarding systems. This chaos forced me onto a later flight while my group waited in Canada, unable to check into our Airbnb or pick up rental cars (as I was the primary booker). The entire incident caused significant business disruption, stress, and additional expenses. I have flown Alaska Airlines previously but will not consider it again without resolution. I request: • Full reimbursement of any additional costs incurred. • Appropriate compensation (vouchers/miles) for the inconvenience and poor service. • Confirmation of corrective actions for Please respond within 7-10 business days. Sincerely, Dr. Chunwen Teng

Never had so many staff members be rude and disrespectful. I had a staff member sarcastically call me “girly” after making me wait 20 minutes to be seen by her. I was able to print my luggage tag and she told me I was too late to check luggage I said the system obviously disagrees. And you had me wait way too long while you asked every single passenger ahead of me about their Disney vacations. She wasted so much time to then say “girly your bag won’t make it on the plane” I’m not her girly I’m a full grown adult. She needs to learn a hell of a lot of respect

My flight was several times rescheduled and then finally canceled.

The flight itself was great. But we had to wait over an hour to deplane so I missed my train. Not the crews fault. They were wonderful!

Flying into PAE was so easy because it’s baggage claim is quick and accesible. I had a car rental and the counter is inside the baggage claim area, very convenient.

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

The first flight was fine, great crew, but the plane was delayed 45 minutes to go to Seattle because of they were missing a ramp. That would make sense if the plane was actually at the gate. Not if we’re still waiting for a plane. After we landed we waited 30-45 minutes on the tarmac just to get off the plane. Alaska made me miss my connecting flight, wasting my time, and my money. I should honestly be reimbursed, but hey, when does the airline ever actually take accountability? Never.

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

It was good. Too long for older people. Service and support was great! Friendly crew!

I had to change my flight last minute due to a medical emergency. Their agent was compassionate and extremely helpful. This airlines really cares about making travel, for fun, work, or an emergency a customer-focused experience. Thank you!

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

Information on your arrival and departure airports