ORD - SBP

$175 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 7/25. 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
$344
Overall average: $247
United Airlines
Wed 8/19Sat 8/29
ORD - SBP • 1 stop
Cheapest one-way
$175
Typical prices: $292-$495
Alaska Airlines
Sat 7/25
ORD - SBP • 1 stop
Top airlines
Cheapest • from $344 (round-trip)
Best reviews • 7.9 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 $472 (round-trip)
Shortest trip • 6h 53m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 44% 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, Aug 19 - Sat, Aug 29
United Airlines Logo
10:35 am - 3:22 pm
ORD
-
SBP
6h 47m
1 stop
United Airlines Logo
5:00 am - 1:30 pm
SBP
-
ORD
6h 30m
1 stop
$344United Airlines
Wed, Oct 28 - Sat, Oct 31
American Airlines Logo
5:00 am - 11:45 am
ORD
-
SBP
8h 45m
1 stop
American Airlines Logo
12:34 pm - 12:06 am
SBP
-
ORD
9h 32m
1 stop
$349American Airlines
Wed, Aug 19 - Sat, Aug 29
American Airlines Logo
5:00 am - 11:52 am
ORD
-
SBP
8h 52m
2 stops
American Airlines Logo
12:29 pm - 11:30 pm
SBP
-
ORD
9h 01m
1 stop
$354American Airlines
Wed, Aug 19 - Sat, Aug 29
American Airlines Logo
5:00 am - 11:52 am
ORD
-
SBP
8h 52m
2 stops
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
$359American Airlines
Thu, Oct 1 - Sun, Oct 4
United Airlines Logo
6:00 am - 10:07 am
ORD
-
SBP
6h 07m
1 stop
United Airlines Logo
2:15 pm - 12:59 am
SBP
-
ORD
8h 44m
1 stop
$383United Airlines
Fri, Oct 9 - Mon, Oct 12
Alaska Airlines Logo
2:21 pm - 11:43 pm
ORD
-
SBP
11h 22m
1 stop
Alaska Airlines Logo
3:36 pm - 11:59 pm
SBP
-
ORD
6h 23m
1 stop
$384Alaska Airlines
Thu, Aug 27 - Mon, Aug 31
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
$389American Airlines
Wed, Oct 28 - Sat, Oct 31
Alaska Airlines Logo
2:21 pm - 11:43 pm
ORD
-
SBP
11h 22m
1 stop
Alaska Airlines Logo
2:25 pm - 2:23 pm
SBP
-
ORD
21h 58m
2 stops
$406Alaska Airlines
Thu, Jul 9 - Mon, Jul 13
American Airlines Logo
5:19 pm - 10:50 pm
ORD
-
SBP
7h 31m
1 stop
American Airlines Logo
12:40 pm - 12:50 am
SBP
-
ORD
10h 10m
1 stop
$419American Airlines
Wed, Oct 28 - Sat, Oct 31
Alaska Airlines Logo
2:17 pm - 7:58 pm
ORD
-
SBP
7h 41m
1 stop
Alaska Airlines Logo
2:25 pm - 2:23 pm
SBP
-
ORD
21h 58m
2 stops
$425Alaska 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 $247 (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

Low seasonJanuary
Cheapest flight$175
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly and prices are also 21% 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 $175 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, Alaska Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to San Luis Obispo are Alaska Airlines and United Airlines. With an average price for the route of $358 and an overall rating of 7.9, Alaska Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $390 and an overall rating of 7.4.

  • 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 3 airlines serving 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.
7.9
Alaska AirlinesOverall score based on 12588 reviews
7.0Food
7.8Comfort
8.1Boarding
8.5Crew
7.0Entertainment
Airline reviews

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

2.0 MediocreJerry, Jan 2026
ORD - SAN
Read more Alaska Airlines reviews

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

My flight got canceled never left san diego and miss out my fam event

Plane seats are comfortable and seemed more roomy than others I have been on. Playing was clean and flight crew friendly. Passengers who have a connecting flight should however be allowed off the plane first

would have been nice for flight to not be delayed by 2 hours so that we had to pay $80 to get home since BART had shut down. i thought a 10pm arrival would leave enough time to account for delays but i was wrong.

I like that volunteers were asked to check in their carryons for free. And then they come out of the carousels within 20 minutes as promised.

The landing was a little rough - but a good flight overall! :)

The issue was not alaska airlines. The ticket you printed was innacurate.

Pretty terrible. The aisles on this flight were too narrow so we had to carry our baby, care seat, luggage, travel stroller step by step down the aisle slowing down a lot of passengers in the process. Not only was this a safety hazard but remember that scene from game of thrones where Cersei walks naked through the streets? It felt about as excruciating as that except both me and my husband were carrying 50lbs of weight while everyone from the flight attendants and passengers dolled out comments like “that stroller doesn’t fit in the overhead compartment and you should check it at the gate” when it is a travel stroller that absolutely fits and did fit in the overhead compartment. The flight said it was 30 min delayed but in actuality we did not take off until 1.5 hours past the original time. It was absolutely terrible. Alaska also charged us 200 dollars just in baggage fees even tho we took the time to buy two check on baggages via their app and bought an extra seat for our child and they still refused to overlook our first time flying with them. Everyone in general looked super miserable and traveling with them with a child is pretty much untenable. Lastly I originally thought I had booked an AM flight for my family but it was a PM flight which I knew was not going to end well since we had a 1.5 year old with us on a flight that gets in 9p. I ended up calling Alaska to try to change the first leg for a change fee, and would even have accepted half of a refund to book a completely different flight but of course they refused and absolutely allowed no flexibility to plans so I guess my revenge was our baby cried for 3 out of the four hour flight and hopefully convinced every miserable person on that flight to never fly Alaska again 🤷🏻‍♀️

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.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

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