$204 Cheap United flights from Chicago to San Luis Obispo (ORD to SBP)

Find The Best Day To Fly from Chicago to San Luis Obispo

Amazing United ORD to SBP Flight Deals

The cheapest flights to San Luis Obispo County Regional found within the past 7 days were $306 round trip and $204 one way. Prices and availability subject to change. Additional terms may apply.

Sat, Nov 1 - Tue, Nov 4
ORD
Chicago
SBP
San Luis Obispo
$306 Roundtrip, found 5 days ago
$306
Roundtrip
found 5 days ago
Select United flight, departing Sat, Nov 1 from Chicago to San Luis Obispo, returning Tue, Nov 4, priced at $306 found 5 days ago
Sat, Nov 1 - Tue, Nov 4
ORD
Chicago
SBP
San Luis Obispo
$319 Roundtrip, found 5 days ago
$319
Roundtrip
found 5 days ago
Select United flight, departing Sat, Nov 1 from Chicago to San Luis Obispo, returning Tue, Nov 4, priced at $319 found 5 days ago

SBP From ORD Economy Coach Packages on Similar Airlines

Price found within the past 48 hours. Click for updated prices.
Pea Soup Andersen's Inn

Pea Soup Andersen's Inn

2.5 out of 5
per person
Oct 17 - Oct 24
found 4 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to San Luis Obispo (SBP)
Sideways Inn

Sideways Inn

3 out of 5
per person
Oct 17 - Oct 24
found 4 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to San Luis Obispo (SBP)
Skyview Hotel - 21 & Over Pool

Skyview Hotel - 21 & Over Pool

3.5 out of 5
per person
Oct 17 - Oct 24
found 4 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Santa Maria (SMX)
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Frequently asked questions

Can I catch a flight from O'Hare Airport to McChesney Field right now?
For any current SBP quarantine requirements and travel advice, visit our Covid-19 Travel Advisor. Look before you book your flight, so you don't get caught up.
What terminal is United Airlines at O'Hare Intl. Airport (ORD)?
Your boarding pass should tell you exactly which terminal your United Airlines flight will be leaving from at O'Hare Intl. Airport (ORD). It might also be able to provide you with arrival details for McChesney Field. If not, it's probably a wise idea to ask your airline.
Are there United Airlines non-stop flights from ORD to SBP?
Expect a stopover when flying from O'Hare Airport to San Luis Obispo County Regional Airport (SBP), as United Airlines doesn't offer direct flights between these two locations. While in transit, you might like to pick up a newspaper or an interesting magazine from the airport bookstore to help pass the time.
How long is a United Airlines flight from ORD to SBP?
Squeeze in some in-flight shut-eye and arrive at your destination well-rested. You'll have sufficient time to do so when traveling with United Airlines between O'Hare Airport and McChesney Field, with the flight taking around 5 hours and 47 minutes.
How many direct and indirect flights does United Airlines fly from ORD to SBP?
You'll enjoy lots of flexibility if you choose to fly with United Airlines from ORD to SBP. At the moment, it operates at least 2 flights per day.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to San Luis Obispo County Regional Airport (SBP), please visit our Customer Service Portal.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Discover our best United flight from Chicago ORD to San Luis Obispo SBP 

To find the best deals on flights to Chicago from San Luis Obispo with United, just enter your travel dates, filter by United, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Chicago ORD to San Luis Obispo SBP with United 

If you’re planning a round trip, booking return flights with United is usually the most cost-effective option. With airfares ranging from $306 to $319, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way United flights from Chicago ORD to San Luis Obispo SBP 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way United flight from Chicago to San Luis Obispo costs from $204. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to San Luis Obispo SBP from  Chicago ORD with United 

To find a cheap United flight from Chicago ORD to San Luis Obispo SBP, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on United flights from Chicago ORD to San Luis Obispo SBP 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as November, or if you book a flight with a stopover. 

 

Find nonstop flights from Chicago ORD to San Luis Obispo SBP with United 

If you’re keen to be on San Luis Obispo soil fast, don’t waste time with a stopover—filter your search results to show direct United flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for United flights from Chicago ORD to San Luis Obispo SBP 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to San Luis Obispo SBP from  Chicago ORD with United on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

United Airports
Hop on a(n) United flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
ORDUSAO'Hare Intl.227
DENUSADenver Intl.226
IAHUSAGeorge Bush Intercontinental136
IADUSAWashington Dulles Intl.100
SFOUSASan Francisco Intl.64
LAXUSALos Angeles Intl.23
EWRUSALiberty Intl.20
FRADEUFrankfurt Intl.19
NRTJPNNarita Intl.19
PEKCHNCapital Intl.16

Travelers ❤️ these 🏨 after their flight to San Luis Obispo

Vagabond Inn San Luis Obispo

Vagabond Inn San Luis Obispo

2 out of 5
210 Madonna Rd, San Luis Obispo, CA
This motel features an outdoor pool, a hot tub, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Free self parking, ...
8.4/10 Very Good! (1,143 reviews)
"Good value and great location. The only complaint I have is that the floors are not totally clean and when you walk around in bare feet they get dirty. But bathroom is clean and room overall is clean. Just the floors need more."

Reviewed on Aug 1, 2025

Vagabond Inn San Luis Obispo
Madonna Inn

Madonna Inn

3.5 out of 5
100 Madonna Road, San Luis Obispo, CA
A full-service spa, 2 restaurants, and 2 outdoor tennis courts are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour ...
9.2/10 Wonderful! (1,224 reviews)
"We heard about Madonna Inn from many friends and since we were going to be in the area we decided to spend 2 nights. As a family we prefer hotels that are newer and no carpet but still wanted to try Madonna Inn. We got a last minute deal and took it. The uniqueness of the rooms are interesting, we ..."

Reviewed on Aug 2, 2025

Madonna Inn
Embassy Suites by Hilton San Luis Obispo

Embassy Suites by Hilton San Luis Obispo

3.5 out of 5
333 Madonna Road, San Luis Obispo, CA
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 8739 conference rooms, free WiFi in public areas, ...
8.4/10 Very Good! (1,157 reviews)
"Food and clean hotel"

Reviewed on Jul 31, 2025

Embassy Suites by Hilton San Luis Obispo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.