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 6/17. 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: $531-$290
American Airlines
Wed 5/6Tue 5/12
ORD - SBP • 1 stop
Cheapest one-way
$138
Typical prices: $340-$543
American Airlines
Wed 6/17
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 $349 (round-trip)
Shortest trip • 7h 11m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% 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

Wed, May 6 - Tue, May 12
American Airlines Logo
5:25 pm - 10:10 pm
ORD
-
SBP
6h 45m
1 stop
American Airlines Logo
4:32 pm - 12:32 am
SBP
-
ORD
6h 00m
1 stop
$275American Airlines
Wed, May 6 - Tue, May 12
Alaska Airlines Logo
8:50 am - 2:59 pm
ORD
-
SBP
8h 09m
1 stop
Alaska Airlines Logo
5:36 pm - 5:05 am
SBP
-
ORD
9h 29m
1 stop
$283Alaska Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
3:07 pm - 10:10 pm
ORD
-
SBP
9h 03m
2 stops
American Airlines Logo
7:02 pm - 5:21 am
SBP
-
ORD
8h 19m
1 stop
$288American Airlines
Tue, Jun 2 - Tue, Jun 9
Alaska Airlines Logo
9:00 am - 2:19 pm
ORD
-
SBP
7h 19m
1 stop
Alaska Airlines Logo
6:00 am - 6:50 pm
SBP
-
ORD
10h 50m
1 stop
$303Alaska Airlines
Wed, May 27 - Tue, Jun 2
American Airlines Logo
5:00 am - 11:47 am
ORD
-
SBP
8h 47m
2 stops
American Airlines Logo
12:51 pm - 12:42 am
SBP
-
ORD
9h 51m
1 stop
$326American Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
5:50 pm - 10:45 pm
ORD
-
SBP
6h 55m
1 stop
American Airlines Logo
12:28 pm - 10:26 pm
SBP
-
ORD
7h 58m
1 stop
$332American Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
3:50 pm - 10:45 pm
ORD
-
SBP
8h 55m
2 stops
American Airlines Logo
12:28 pm - 10:26 pm
SBP
-
ORD
7h 58m
1 stop
$337American Airlines
Wed, May 6 - Tue, May 12
American Airlines Logo
3:07 pm - 10:10 pm
ORD
-
SBP
9h 03m
2 stops
American Airlines Logo
4:32 pm - 12:32 am
SBP
-
ORD
6h 00m
1 stop
$344American Airlines
Thu, May 7 - Mon, May 11
American Airlines Logo
3:00 pm - 10:10 pm
ORD
-
SBP
9h 10m
1 stop
American Airlines Logo
4:32 pm - 12:32 am
SBP
-
ORD
6h 00m
1 stop
$349American Airlines
Tue, Apr 21 - Sat, Apr 25
United Airlines Logo
2:35 pm - 9:35 pm
ORD
-
SBP
9h 00m
1 stop
United Airlines Logo
5:00 am - 1:12 pm
SBP
-
ORD
6h 12m
1 stop
$362United 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 May.

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 31% drop in price.
Most popular time to fly and prices are also 16% 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 $426 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 9562 reviews
7.1Entertainment
7.7Boarding
6.6Food
8.1Crew
7.3Comfort
Airline reviews

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

2.0 MediocreAaron, Apr 2026
ORD - BNA
Read more United Airlines reviews

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!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

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

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

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

Information on your arrival and departure airports