ORD - SBP

$180 Find Cheap Flights from Chicago to San Luis Obispo - 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 Chicago to San Luis Obispo departing on 8/19. 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
$344
United Airlines
Tue 8/11Sat 8/22
ORD - SBP • 1 stop
Cheapest one-way
$180
Typical prices: $115-$229
Alaska Airlines
Wed 8/19
ORD - SBP • 1 stop
Top airlines
Cheapest • from $344 (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
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Insights
Top layover airports
Cheapest • Avg $472 (round-trip)
Shortest trip • 6h 53m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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 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, Aug 11 - Sat, Aug 22
United Airlines Logo
1:58 pm - 7:47 pm
ORD
-
SBP
7h 49m
1 stop
United Airlines Logo
5:00 am - 1:30 pm
SBP
-
ORD
6h 30m
1 stop
$344United Airlines
Fri, Aug 21 - Fri, Aug 28
Alaska Airlines Logo
8:17 pm - 2:44 pm
ORD
-
SBP
20h 27m
1 stop
Alaska Airlines Logo
3:24 pm - 11:59 pm
SBP
-
ORD
6h 35m
1 stop
$348Alaska Airlines
Fri, Nov 6 - Sun, Nov 8
United Airlines Logo
3:40 pm - 9:53 pm
ORD
-
SBP
8h 13m
1 stop
United Airlines Logo
4:25 pm - 12:58 am
SBP
-
ORD
6h 33m
1 stop
$349United Airlines
Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
6:00 am - 11:39 am
ORD
-
SBP
7h 39m
1 stop
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
$354American Airlines
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
1 stop
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
$355American Airlines
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
6:00 am - 11:39 am
ORD
-
SBP
7h 39m
1 stop
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
$356American Airlines
Tue, Aug 11 - Sat, Aug 22
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
2 stops
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
$359American Airlines
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
2 stops
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
$360American Airlines
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
2 stops
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
$361American Airlines
Tue, Nov 3 - Tue, Nov 3
Alaska Airlines Logo
7:25 am - 1:47 pm
ORD
-
SBP
8h 22m
1 stop
Alaska Airlines Logo
5:41 pm - 5:40 am
SBP
-
ORD
9h 59m
1 stop
$362Alaska 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 August.

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 August, where tickets cost $0 (return) on average. On the other hand, the most expensive months are September and December, where the average cost of round-trip tickets is $678 and $656 respectively.

Good to know

Cheapest flight$180
Most popular time to fly and prices are also 24% 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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San Luis Obispo was $180 for a one-way ticket and $344 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 $368 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 9948 reviews
8.1Crew
6.7Food
7.7Boarding
7.3Comfort
7.1Entertainment
Airline reviews

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

2.0 Mediocremary kay, Jul 2026
ORD - LAX
Read more United Airlines reviews

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

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.

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

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

A bit rush for transit. Food and entertainment are not available

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

My flight was delayed for a whole day, so I lost a day of my vacation.

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

Dallas Hub. American taking ownership for their screwups instead of blaming their contractors and customers, trading their people, their call in service, reservation agents and their ticketing process. Make sure wheelchairs are available especially when the request is in their record.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Boarding was a mess - the agent basically called every group in rapid succession, so there was no organization at all. The economy seats are a joke, and main cabin extra seats were sold out when I purchased my flight. As such, I was locked in the same position for four hours. Being 6’6”, it was impossible to get my bag out from under the seat in front of me, and I couldn’t have used my laptop even if my bag were accessible due to the minuscule seat pitch. Also the wifi was broken. American is a joke - can’t wait until they merge with Spirit.

Horrible scam. Make you pay extra for more leg room then switch your seat as you’re boarding to a regular seat. Never fly American!

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

Information on your arrival and departure airports