ORD - SBP

$138 Find Cheap Flights from Chicago to San Luis Obispo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Luis Obispo departing on 7/15. 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 San Luis Obispo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Luis Obispo, 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 Chicago to San Luis Obispo, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$275
Typical prices: $493-$437
Alaska Airlines
Tue 6/2Sat 6/6
ORD - SBP • 1 stop
Cheapest one-way
$138
Typical prices: $444-$535
United Airlines
Wed 7/15
ORD - SBP • 1 stop
Top airlines
Cheapest • from $275 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and San Luis Obispo. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $355 (round-trip)
Shortest trip • 7h 09m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 San Luis Obispo!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to San Luis Obispo (ORD-SBP)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San Luis Obispo 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 Chicago to San Luis Obispo

Tue, Jun 2 - Sat, Jun 6
Alaska Airlines Logo
2:10 pm - 11:53 pm
ORD
-
SBP
11h 43m
1 stop
Alaska Airlines Logo
2:59 pm - 11:55 pm
SBP
-
ORD
6h 56m
1 stop
$275Alaska Airlines
Sat, May 23 - Sat, May 30
Alaska Airlines Logo
7:59 pm - 2:19 pm
ORD
-
SBP
20h 20m
1 stop
Alaska Airlines Logo
2:59 pm - 11:55 pm
SBP
-
ORD
6h 56m
1 stop
$289Alaska Airlines
Mon, Jun 1 - Sat, Jun 6
Alaska Airlines Logo
9:00 am - 2:19 pm
ORD
-
SBP
7h 19m
1 stop
Alaska Airlines Logo
2:59 pm - 11:55 pm
SBP
-
ORD
6h 56m
1 stop
$312Alaska Airlines
Tue, Jun 2 - Sat, Jun 6
American Airlines Logo
3:50 pm - 10:45 pm
ORD
-
SBP
8h 55m
2 stops
American Airlines Logo
12:28 pm - 11:00 pm
SBP
-
ORD
8h 32m
1 stop
$317American Airlines
Sat, May 23 - Sat, May 30
American Airlines Logo
11:50 am - 6:22 pm
ORD
-
SBP
8h 32m
2 stops
American Airlines Logo
12:51 pm - 12:42 am
SBP
-
ORD
9h 51m
1 stop
$327American Airlines
Sat, May 9 - Sat, May 16
United Airlines Logo
7:00 am - 1:31 pm
ORD
-
SBP
8h 31m
1 stop
United Airlines Logo
2:15 pm - 11:29 pm
SBP
-
ORD
7h 14m
1 stop
$335United Airlines
Fri, May 22 - Tue, May 26
Alaska Airlines Logo
2:10 pm - 11:53 pm
ORD
-
SBP
11h 43m
1 stop
Alaska Airlines Logo
6:00 am - 6:50 pm
SBP
-
ORD
10h 50m
1 stop
$336Alaska Airlines
Sat, Jun 6 - Wed, Jun 10
Alaska Airlines Logo
9:00 am - 2:19 pm
ORD
-
SBP
7h 19m
1 stop
Alaska Airlines Logo
5:57 pm - 1:21 pm
SBP
-
ORD
17h 24m
1 stop
$347Alaska Airlines
Wed, Jul 22 - Sun, Jul 26
Alaska Airlines Logo
2:20 pm - 11:40 pm
ORD
-
SBP
11h 20m
1 stop
Alaska Airlines Logo
5:57 pm - 1:21 pm
SBP
-
ORD
17h 24m
1 stop
$349Alaska Airlines
Sat, May 9 - Sat, May 16
American Airlines Logo
3:07 pm - 10:10 pm
ORD
-
SBP
9h 03m
2 stops
American Airlines Logo
12:55 pm - 11:48 pm
SBP
-
ORD
8h 53m
1 stop
$360American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to San Luis Obispo flights

Get data-powered insights and trends into flights from Chicago to San Luis Obispo to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to San Luis Obispo?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to San Luis Obispo departing in June.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to San Luis Obispo?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to San Luis Obispo, 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 Chicago O'Hare Intl Airport to San Luis Obispo is January, where tickets cost $288 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $599 and $586 respectively.

Good to know

Low seasonJanuary
Cheapest flight$138
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Chicago to San Luis Obispo

When to book flights from Chicago to San Luis Obispo

Are your dates flexible? Find out the best times to travel from Chicago to San Luis Obispo 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 Chicago to San Luis Obispo flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to San Luis Obispo?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San Luis Obispo was $138 for a one-way ticket and $275 for a round-trip.

  • Do I need a passport to fly between Chicago and San Luis Obispo?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago to San Luis Obispo?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to San Luis Obispo?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and San Luis Obispo, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to San Luis Obispo, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to San Luis Obispo are United Airlines and American Airlines. With an average price for the route of $390 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $436 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to San Luis Obispo?

    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 Chicago to San Luis Obispo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San Luis Obispo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Luis Obispo from Chicago 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 Chicago to San Luis Obispo?

    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 San Luis Obispo with an airline and back to Chicago with another airline. Booking your flights between Chicago and SBP 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 Chicago to San Luis Obispo?

    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 San Luis Obispo from Chicago 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 Chicago to San Luis Obispo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Luis Obispo. 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 Chicago to San Luis Obispo? 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.
7.4
United AirlinesOverall score based on 9680 reviews
8.1Crew
6.6Food
7.7Boarding
7.3Comfort
7.1Entertainment
Airline reviews

A long delay. Don't travel late in the day.

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight from Chicago to San Luis Obispo

Information on your arrival and departure airports