STS - ORD

$150 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 10/7. 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

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Everything you should know

Cheapest round-trip
$298
American Airlines
Wed 8/26Wed 9/2
STS - ORD • 1 stop
Cheapest one-way
$150
Delta
Wed 10/7
STS - ORD • 1 stop
Top airlines
Cheapest • from $298 (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 $318 (round-trip)
Shortest trip • 6h 17m (one-way)
Insights
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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

Wed, Aug 26 - Wed, Sep 2
American Airlines Logo
12:58 pm - 10:00 pm
STS
-
ORD
7h 02m
1 stop
American Airlines Logo
6:59 am - 12:28 pm
ORD
-
STS
7h 29m
1 stop
$298American Airlines
Mon, Sep 21 - Wed, Sep 23
Alaska Airlines Logo
6:47 pm - 1:22 pm
STS
-
ORD
16h 35m
1 stop
Alaska Airlines Logo
6:00 am - 12:46 pm
ORD
-
STS
8h 46m
1 stop
$299Alaska Airlines
Mon, Sep 21 - Thu, Sep 24
Alaska Airlines Logo
6:13 am - 7:21 pm
STS
-
ORD
11h 08m
1 stop
Alaska Airlines Logo
8:17 pm - 9:54 am
ORD
-
STS
15h 37m
1 stop
$299Alaska Airlines
Thu, Aug 20 - Sat, Aug 29
American Airlines Logo
12:58 pm - 11:30 pm
STS
-
ORD
8h 32m
1 stop
American Airlines Logo
6:59 am - 12:28 pm
ORD
-
STS
7h 29m
1 stop
$299American Airlines
Wed, Aug 26 - Wed, Sep 2
American Airlines Logo
12:58 pm - 10:00 pm
STS
-
ORD
7h 02m
1 stop
American Airlines Logo
6:59 am - 12:28 pm
ORD
-
STS
7h 29m
1 stop
$299American Airlines
Sat, Dec 12 - Tue, Dec 15
Alaska Airlines Logo
7:12 am - 5:01 pm
STS
-
ORD
7h 49m
1 stop
Alaska Airlines Logo
2:03 pm - 7:45 pm
ORD
-
STS
7h 42m
1 stop
$299Alaska Airlines
Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
12:58 pm - 11:30 pm
STS
-
ORD
8h 32m
1 stop
American Airlines Logo
6:00 am - 12:09 pm
ORD
-
STS
8h 09m
1 stop
$300American Airlines
Sat, Sep 12 - Tue, Sep 15
American Airlines Logo
1:08 pm - 11:43 pm
STS
-
ORD
8h 35m
1 stop
American Airlines Logo
6:59 am - 12:38 pm
ORD
-
STS
7h 39m
1 stop
$300American Airlines
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
12:58 pm - 11:30 pm
STS
-
ORD
8h 32m
1 stop
American Airlines Logo
5:00 am - 12:28 pm
ORD
-
STS
9h 28m
1 stop
$304American Airlines
Sat, Dec 12 - Tue, Dec 15
Alaska Airlines Logo
7:12 am - 5:01 pm
STS
-
ORD
7h 49m
1 stop
Alaska Airlines Logo
2:03 pm - 7:45 pm
ORD
-
STS
7h 42m
1 stop
$319Alaska 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 American Airlines ($298) and Alaska Airlines ($299).

Good to know

Cheapest flight

$150
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 $150 for a one-way ticket and $298 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 12728 reviews
8.5Crew
7.0Food
8.1Boarding
7.8Comfort
7.0Entertainment
Airline reviews

Only issue is that when you board last they make you check your carry on due to lack of space. Did not care for that.

8.0 ExcellentAnonymous, Jul 2026
SAN - ORD
Read more Alaska Airlines reviews

Only issue is that when you board last they make you check your carry on due to lack of space. Did not care for that.

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

My flight was several times rescheduled and then finally canceled.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Broke the wheels of my luggage. Should be more gentle with other peoples belongings. Very upset about needing a new suitcase before Christmas.

There was no coffee on the flight. I was very surprised. I know it is a small thing, but they seemed to have run out of other drinks.

If Alaska Air is going to partner with other airlines, then it has to make the transition to the connecting flight better, especially if Alaska Air is the one that is running late. When I realized our 30 minutes of lateness due to weather was going to make getting to my connecting flight home more difficult ,I would have expected more from the crew than blank stares and "sorry". My son and I had 20 minutes to get from Gate E to the end of Gate K in the Chicago airport. My 50+ year-old body had to sprint and yell to get through the throngs and have any chance of arriving to the gate on time. In addition, the seats I had chosen when I purchased the connecting flight were changed so that my son and I placed in the last rows next to the bathrooms and were separated. There needs to be better communication between the airlines if one is going to be late. The thought of not making it home on time (we still had an 1.5 hour drive to get there) was stressful and unnecessary.

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

Information on your arrival and departure airports