STS - ORD

$133 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 5/2. 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
$265
Alaska Airlines
Tue 4/14Tue 4/21
STS - ORD • 1 stop
Cheapest one-way
$133
Alaska Airlines
Sat 5/2
STS - ORD • 1 stop
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 $379 (round-trip)
Shortest trip • 6h 35m (one-way)
Insights
Insights
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Insights
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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, Apr 14 - Tue, Apr 21
Alaska Airlines Logo
7:00 am - 6:40 pm
STS
-
ORD
9h 40m
1 stop
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
$265Alaska Airlines
Tue, Apr 14 - Mon, Apr 20
Alaska Airlines Logo
7:00 am - 6:40 pm
STS
-
ORD
9h 40m
1 stop
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
$285Alaska Airlines
Tue, Apr 14 - Tue, Apr 21
Alaska Airlines Logo
7:00 am - 6:40 pm
STS
-
ORD
9h 40m
1 stop
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
$287Alaska Airlines
Mon, Apr 13 - Tue, Apr 21
Alaska Airlines Logo
7:46 pm - 2:21 pm
STS
-
ORD
16h 35m
1 stop
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
$289Alaska Airlines
Tue, Apr 14 - Wed, Apr 22
Alaska Airlines Logo
7:00 am - 6:40 pm
STS
-
ORD
9h 40m
1 stop
Alaska Airlines Logo
6:00 am - 12:21 pm
ORD
-
STS
8h 21m
1 stop
$291Alaska Airlines
Tue, May 5 - Sat, May 9
Alaska Airlines Logo
10:01 am - 11:59 pm
STS
-
ORD
11h 58m
2 stops
Alaska Airlines Logo
8:50 am - 7:06 pm
ORD
-
STS
12h 16m
1 stop
$294Alaska Airlines
Thu, Apr 16 - Mon, Apr 20
Alaska Airlines Logo
7:00 am - 7:02 pm
STS
-
ORD
10h 02m
1 stop
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
$305Alaska Airlines
Mon, Apr 13 - Mon, Apr 20
Alaska Airlines Logo
7:46 pm - 2:21 pm
STS
-
ORD
16h 35m
1 stop
Alaska Airlines Logo
4:10 pm - 11:13 pm
ORD
-
STS
9h 03m
1 stop
$309Alaska Airlines
Thu, Apr 16 - Wed, Apr 22
Alaska Airlines Logo
7:00 am - 7:02 pm
STS
-
ORD
10h 02m
1 stop
Alaska Airlines Logo
6:00 am - 12:21 pm
ORD
-
STS
8h 21m
1 stop
$311Alaska Airlines
Sat, Apr 25 - Tue, Apr 28
Alaska Airlines Logo
7:46 pm - 6:40 am
STS
-
ORD
8h 54m
1 stop
Alaska Airlines Logo
3:52 pm - 10:58 am
ORD
-
STS
21h 06m
1 stop
$315Alaska 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.

What is the most popular layover airport when flying from Santa Rosa to Chicago?

Percentage of 1-stop round-trip flights from Santa Rosa to Chicago chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Seattle (SEA) is the top choice – 44% of KAYAK users who clicked on 1-stop flights from Santa Rosa to Chicago picked an itinerary connecting there.

What is the cheapest layover airport when flying from Santa Rosa to Chicago?

Average round-trip price for 1-stop flights from Santa Rosa to Chicago clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Seattle (SEA) offer the most affordable fares, with an average round-trip price of $379.

Which layover airport offers the shortest total travel time from Santa Rosa to Chicago?

Shortest average total travel time for 1-stop one-way flights from Santa Rosa to Chicago via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Phoenix (PHX) for the shortest journey. The average one-way travel time for flights connecting there is 6h 35m.

Which layover airport has the quickest connection when flying from Santa Rosa to Chicago?

Average layover duration at different layover airports for 1-stop one-way flights from Santa Rosa to Chicago, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Phoenix (PHX) often has the shortest layovers from Santa Rosa to Chicago, with an average of 1h 01m.

Good to know

Cheapest flight$133
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 $133 for a one-way ticket and $265 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 $429 and an overall rating of 7.9, 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 7.1.

  • 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.
7.9
Alaska AirlinesOverall score based on 12075 reviews
7.0Entertainment
7.0Food
8.1Boarding
8.5Crew
7.8Comfort
Airline reviews

I have been flying commercial for decades. I was in one of the ladder boarding groups, had my bag tagged because they thought there was not going to be enough space for it in the overhead bins. I politely asked one of the attendance if I could try to find a space- she said I could and I did. I then took the bag tag off and gave it to one of the other attendants as I was told to do by the first one. He, in a curt, anal, and disrespectful manner, told me that I needed to take my bag down from the overhead bin and check it. This was a situation I’ve never encountered before. The attendant’s attitude was confrontational and belittling in front of other onlooking passengers as if daring me to challenge him. I am a physician who takes care of patients day in and day out. Not wanting to make a scene, I calmly told him, “do what you need to do.” he took my bag down from the overhead bin, put the back tag back on it, and checked it only to make room for another bag that was also supposed to be technically checked by a following passenger. The same male attendant later came up to me and said “you shouldn’t have showed me the bag tag,” as if conveying that he was just following protocol was a justification for treating me like a kid out of line. I cared about this because it took 15 minutes from my life to then retrieve the bag at baggage claim and it also felt like really poor customer service. I understand the need for protocols. This is also a service industry, and we the passengers are the clients. We should be made to feel welcome and respected and our life in transit made as easy as it can be within reason. This attendant clearly needs to be reminded of that. Of note, an older female fellow passenger sitting next to me agreed with this assessment.

4.0 OkayAlex, Mar 2026
SFO - SAN
Read more Alaska Airlines reviews

I have been flying commercial for decades. I was in one of the ladder boarding groups, had my bag tagged because they thought there was not going to be enough space for it in the overhead bins. I politely asked one of the attendance if I could try to find a space- she said I could and I did. I then took the bag tag off and gave it to one of the other attendants as I was told to do by the first one. He, in a curt, anal, and disrespectful manner, told me that I needed to take my bag down from the overhead bin and check it. This was a situation I’ve never encountered before. The attendant’s attitude was confrontational and belittling in front of other onlooking passengers as if daring me to challenge him. I am a physician who takes care of patients day in and day out. Not wanting to make a scene, I calmly told him, “do what you need to do.” he took my bag down from the overhead bin, put the back tag back on it, and checked it only to make room for another bag that was also supposed to be technically checked by a following passenger. The same male attendant later came up to me and said “you shouldn’t have showed me the bag tag,” as if conveying that he was just following protocol was a justification for treating me like a kid out of line. I cared about this because it took 15 minutes from my life to then retrieve the bag at baggage claim and it also felt like really poor customer service. I understand the need for protocols. This is also a service industry, and we the passengers are the clients. We should be made to feel welcome and respected and our life in transit made as easy as it can be within reason. This attendant clearly needs to be reminded of that. Of note, an older female fellow passenger sitting next to me agreed with this assessment.

Ended up sitting in front of a child who kicked the back of the seat and screamed for most of the flight.

After landing in Seattle, 3 hours waiting to find parking space do to driving problems. Very uncomfortable.

My only complaint was how far it was from plane to baggage claim

I had a problem with my reservation and no one could help me understand what happened. I booked my flight months ago and received a confirmation email. In the confirmation email, it said that the flight would depart at 3:15 p.m. A few hours before the flight, I tried to go online and check in, and suddenly it said that the flight was leaving an hour earlier. I had to rush to get to the airport and almost didn't make it. No one could help me understand why this happened, and I'm really concerned that it might happen in the future. I would appreciate some support in this matter.

They cancelled the flight and provided no support to find another way home or how to get a refund. Links provided didn’t work and phone wait times were over eight hours. Battery on my phone couldn’t last long enough.

It was a super old plane so the first class experience was just not luxurious

signage from the upper area to the tram down 2 escalator!

You sent me an email saying boarding was at 9:29 and AA sent one that was 8:29 on Sunday morning. I had to call AA to get that it was indeed 8:29.

Not bad. Due to not buying a seat, on the way back, my seat was not assigned till 2 hrs before the flight left. Got me worried I wouldn’t have a seat.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

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

Information on your arrival and departure airports