Find cheap flights from Chicago to San Luis Obispo


Find cheap flights from Chicago to San Luis Obispo

Search hundreds of travel sites at once for deals on flights to San Luis Obispo

Chicago (ORD)
San Luis Obispo County
Wed 4/21
Wed 4/28
Any month
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Good to know

Low season

JulyBest time to beat the crowds with an average 21% drop in price.

High season

JuneMost popular time to fly with an average 14% increase in price.

Average price round-trip

$385(avg. price over the last 2 weeks)

Good deal round-trip

$347or less

Good deal one-way

$154or less

Book cheap flights from Chicago to San Luis Obispo

When to book flights from Chicago to San Luis Obispo

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $154 or less one-way and $347 or less round-trip.
  • High season is considered to be May, June and July. The cheapest month to fly is July.
  • Morning departure is around 41% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Chicago to San Luis Obispo flights

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Top 3 airlines serving Chicago O'Hare Intl to San Luis Obispo County

Scores according to KAYAK customer reviews

Alaska Airlines
Overall score based on 29,326 reviews
Airline reviews

Cons: "Alaska is great I love theM"

Pros: "Crew was very nice."
Cons: "Consistency - nuts on way to Chicago were warm while on way back cold."

Cons: "It was a little chilly."

Cons: "Better snacks. No cost for checked first luggage"

Cons: "Nothing. I've flown on worse."

Pros: "It’s not American, United, or Delta."
Cons: "The Gogo Internet access was much worse than non-existent, causing me to pay and waste literally hours trying to get a single flight search done on [This idiotic form is broken—the search engine that starts with “Kaya”], and now I have to waste more time and effort to demand a refund from Gogo."

Pros: "Selection of entertainment on a BYO-device was good, especially in the movies category"
Cons: "Weather-related delay is certainly not Alaska’s fault, but the 10-minutes waiting for a gate after landing was excruciating after such a long delay in the first place"

Pros: "Alaska is a great airline."
Cons: "Free food would be awesome."

Pros: "Good communication re: the delay, comfy seats, super friendly gate staff, great free movie selection"
Cons: "Not sitting at the gate on the plane for 2+ hours:("

Pros: "Average"
Cons: "Seat back screens. More space."

Pros: "The crew did very well. The seats could have been a little more comfortable, the lumbar could have been a bit more stiff for lower back support, the arm rest up and down function did not work, and a little more space between rows and seats would have made it more comfortable."
Cons: "The seats could have been a little more comfortable, the lumbar could have been a bit more stiff for lower back support, the arm rest up and down function did not work, and a little more space between rows and seats would have made it more comfortable. The bathroom was too narrow."

Pros: "Timing-Fasrer than scheduled"

Pros: "Great! Decent."

Cons: "Delayed. Flue season folks. If your sick just don’t travel!"

Pros: "Everything went smooth and was great besides the boarding."
Cons: "Boarding seemed to take quite quite awhile, not sure what the deal was but once we were boarded they kicked it into high gear"

Cons: "Dog allowed to sit next to me. It should be ina crate or at least on the lap of the owner"

Pros: "All good"

Cons: "Delayed"

Pros: "Time of flight is not delayed and arrival time is even ahead of the estimated time."

Pros: "Nothing."
Cons: "We were sitting in the plane on the tarmac for 3 hours waiting to take off. The crew did a very poor job announcing what was going on."

Cons: "They did not provide sanck for 4 hr flight and they should keep a few spare head phone"

Pros: "First time on Alaska. Great experience."

Pros: "Nice movies Comfortable seats"
Cons: "Noisy air con Seat not reclining Headphone jack not working No storage space"

Pros: "Alaska airlines much better than United or American in terms of friendly service, wifi and battery charge, and entertainment options"

Pros: "crew's upbeat attitude"
Cons: "very limited drink choices"

Pros: "We especially liked the in flight movies which you could rent on a tablet like device similar in size to an iPad. Also, we appreciate airlines that still board the plane by row starting in the rear. That is the most sensible way to board a plane. Also, I had plenty of legroom while seated."
Cons: "Nothing to complain about."

Pros: "This was a completely booked flight during Xmas week, and the flight was delayed an hour. Alaska Air did a great job of accommodating these difficulties. When I checked in online they had a notice asking if we would volunteer to check bags for free because they knew overhead space would be tight. Once the flight was underway they announced they'd been able to reroute to save us some of that time. And the Alaska Air/Horizon connecting flight was also delayed, most likely to accommodate this large flight. The aircraft is wonderful--the plugs for devices at every seat plus free entertainment piped to our devices really helps to pass the time."
Cons: "Person announcing the boarding needs some enunciation lessons. She spoke too quickly and on top of (or below) other announcements and even kept talking when she was doing something beneath the podium, so no chance to read lips."

Pros: "Friendly staff, comfortable seats"

Cons: "The USB charger on my seat was broken"

Pros: "Excellent experience all around on all flights."

Pros: "I try to book Alaska when I can, they have good leg room for a taller person and their baggage fees are not outrageous like Spirit. You can tell the crew is not completely miserable doing their jobs and treat you like a human most of the time."

Pros: "Love the amount of space availabile for my legs!!"

Pros: "First time flying Alaskan. Out of all the US-based airlines I flew with, Alaskan was the cleanest, friendliest, and quickest."

Pros: "Friendliness"

Pros: "The flight attendants made quite a few passes through to make sure everyone had drinks."
Cons: "We were very delayed in taking off because the copilot wasn't there. Many people had connecting flights and the crew did nothing to help them get off the plane first or give any kind of reasrrances that they could make the flight."

Pros: "Free movies!"

Cons: "Customers should be made aware that animals are on the flight before boarding to safe guard against allergies."

Pros: "First off Bonnie at the boarding gate was phenomenal , She has an amazing disposition ( especially at 5:00 in the morning ) she greeted each and every customer by name and with a smile ! Our flight was delayed for 2 hours as we sat at the gate while problems were fixed . The Captain made sure he kept us informed as each problem occurred and was fixed . The rest of the flight crew remained patient and attentive , which of course kept all the customers onboard calm and patient as well . My daughter just moved to Seattle and if this is the norm for this airline I will continue to use them for my future visits ! Elizabeth"

Cons: "Can I have a refund? My flight has been delayed 3 1/2 hours and then they add another delayed flight to leave from my gate ahead of us. Wonderful."

Pros: "Efficient and comfortable"

Pros: "The plane was new but with no bells let alone whistles."
Cons: "No monitors/screens at all on plane."

Cons: "My initial flight was at 0800; I got to the gate before 0800 and was told I couldn't board the flight even though it was still at the gate and was still before the flight time. I had to pay to rebook my flight, spent over $200 in rides to and from airport, had additional parking fees and was several hours late to work. I have many family members who work in flight service so I understand that employees don't like to re-do paperwork; however, being there before the flight time and being denied cost a lot of work time and money. I have always had great experiences with Alaska so this one was quite a disappointment compared to their usual great service. :("

Pros: "Very accommodating staff"

Pros: "Was seated by a very nice couple."
Cons: "The plane was crowded. I was very upset to find that on a 6 hour flight I not only had to pay for entertainment I didn't even get to finish watching what I paid for. Was really pissed that on a 6 hour flight I had to starve because you also charge for food! Didn't have a credit card only cash that was refused so I was unable to eat."

Pros: "Boarding was fast"
Cons: "Space between the rows is narrow, I understand it has nothing to do with the flight itself."

Pros: "New equipment"
Cons: "Sparse food."

Pros: "I love the leg room on Alasks flights, and I'm always impressed by the professionalism and respect Alaska employees show to their customers."

Pros: "I am a tall woman and rarely ride in an airplane without my kneecaps brushing the seat in front of me in coach. Not sure what Alaska Airlines is doing differently, but I had knee-room to spare on my flight to Seattle!"
Cons: "Upon our arrival in Seattle, it seemed that the gate wasn't quite ready for us and we spent a restless few minutes "getting docked" for departure."

Pros: "My flight out of Chicago was delayed for about 3 hours and was no way I was going to catch my connecting flight in Seattle. I called Alaska airlines customer service and they were able to get me rescheduled on two new flights from Chicago to Fairbanks the very next day!! Excellent!!"

Pros: "The airplale MD 80 are old"

Pros: "On time"
Cons: "Seating"

Pros: "mango juice and soft blankets"
Cons: "too much time between meals"

Pros: "Clean environment of the terminals and the speed of the shuttle."
Cons: "no comment."

Pros: "It took off on time and life was good."

Pros: "Great service!"

Pros: "Everything"

Cons: "Same as previous response."

Pros: "The entertainment was amazing"
Cons: "We were delayed multiple times and landed extremely late"

Pros: "Very affordable! Traveling can be difficult, especially from Chicago O'hare - one of the busiest airports in the country - but everything was made easy for me and was a breeze!"
Cons: "No complaints here!"

Pros: "Almost always on time, captain keeps us updated, friendly airline staff"
Cons: "Nothing"

Pros: "On time"

Pros: "Everyone was polite, helpful, and courteous."

Pros: "There were too many gate changes ."

Pros: "I like that they have complimentary snacks"

Cons: "Delay boarding and then dropped us off at a remote runway and had to wait 45 minutes for a bus to main terminal!"

Pros: "Nothing"
Cons: "4 hora de retraso ni una cortesía empleados bien carnepuercos"

Pros: "Price space, time"
Cons: "Waiting.. but better to be early than late"

Pros: "Everything was pretty decent.. Best part was the price.. Boarding was good staff was good"
Cons: "Wasn't enough room.. kind of tight.. Couple more inches all around would have been perfect though"

Pros: "Ease of travel"

Pros: "Everything"
Cons: "No dislikes"

Pros: "No complaints"

Pros: "N/A"
Cons: "The flights were delayed multiple times. No communication at your gates. Oh and I think my favorite was changing terminals and gates 5 TIMES within 1 hour at DFW! RIDICULOUS AND UNACCEPTABLE. NEVER AGAIN!"

Pros: "All personnel where polite,helpful, and respectful. Greg to have wifi and power chargers."
Cons: "There was no real entertainment on the screens. No movies."

Pros: "Everybody was nice my ride was comfortable and they treat me with respect"
Cons: "I like everything"

Pros: "On time."

Cons: "1 hour late. And when the pilot made announcements during the movie it would not pause. We missed parts of the movie. It was annoying."

Pros: "very good no problems.."
Cons: "all good thanks much"

Cons: "Delayed"

Pros: "The ride was smooth the airplane was the food was OK the stewardess were kind"
Cons: "The ride was smooth the airplane was the food was OK the stewardess were kind"

Pros: "Nothing"
Cons: "Constant delays and cancellenations"

Pros: "Smooth, simple and easy process. Over good experience."
Cons: "I got nothing here."

Cons: "Same as above but I missed a whole day with my relatives at the lake :("

Pros: "The movies"
Cons: "Everything else"

Pros: "That I got a soda"
Cons: "Delayed at Ohare by an hour. Sitting on the Tarmac for a half hour in Reagan, waiting for a gate. This was our leg back to DC, after our leg to Chicago four days previously. On that trip I did a review and gave the whole trip a 1 out of 5 stars. That trip was the trip from hell, with delays, waiting on the Tarmac, deplaning, almost cancelled, more waiting on the Tarmac, wheels up in Reagan, wheels down in ORD, and then more Tarmac waiting for a gate. So I was already more than perturbed when this trip had similar outcomes."

Pros: "Love bed it! Would recommend to family/friends"

Pros: "Smooth trip"
Cons: "Delay delay delay on the flights"

Pros: "I loved the entertainment options"
Cons: "I did not like"

Pros: "It was a good nice ride. The employee was nice."

Cons: "No AC or USB charging ports, no individual entertainment screens."

Cons: "We wait to long for the connection"

Pros: "Rough landing"

Pros: "Everyone was friendly and helpful"

Pros: "Price no delays"
Cons: "Nothing"

Cons: "Out of certain food items that should have been available"

Pros: "The chairs where comfortable and there was a free movie"
Cons: "The sound for the movie didn't work, the atenders dI'd not do any thing tI make uo for it. There was no complimentary snack. Loading on was a mess, not organized well."

Pros: "Everything"
Cons: "Nothing"

Pros: "We had a small technical glitch and the pilot kept us updated. Nothing is more difficult than not knowing what is going on."

Cons: "Horrible delays and many gate changes"

Cons: "There's no room for non skinny people. It was awful"

Pros: "Great service"
Cons: "Waiting an hour to take off"

Pros: "Everything"
Cons: "Keep improving for sustainability in market. Best"

Cons: "Everything was great"

Pros: "Nothing"
Cons: "The fact that it hasn't left yet and it won't leave until 8pm."

Pros: "Finally sitting in my seat"
Cons: "3 hrs late sucks"

Pros: "They know their business"
Cons: "No free Internet. Costs too outrageous."

Pros: "I enjoyed an on time departure and early arrival."

Pros: "The service since I am handicap"

Cons: "Good"

Cons: "Nothing"

Pros: "Pilot helped with luggage. I was using a cane and c sm very v short"

Cons: "Same as above"

Cons: "Tv was subpar"

Pros: "The directTV was great."

Pros: "Loved the Great Falls airport!! Who goes to an airport that has leather couches that you can lay down on and take a quick nap!! Beautiful airport!!"

Cons: "You are required to pay to watch the tv. It's free with Delta."

Pros: "Excellent all the way!"
Cons: "It took about 30 minutes to get luggage in Atlanta"

Pros: "easy transfer"
Cons: "had to transfer"

Cons: "Left about 15 minutes late."

Pros: "same as above"
Cons: "same as above"

Pros: "ontime"
Cons: "At least one check-in baggage should be free for the price."

Pros: "Overall service."
Cons: "Impolite Lady Gate Agent."

Cons: "Too cramped, fligjt delay of over an hour"

Cons: "lost our bag, crying babies, uncomfortable plane"

Pros: "Everything was on time"

Pros: "Overall fine"

Cons: "Why should I have to pay to watch tv? I know you don't have to pay on Southwest, Virgin America or Jet Blue. Not sure that a very (and I mean VERY SMALL) snack can be considered food"

Pros: "On time, gates were close together"

Cons: "The delay"

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

Cons: "Deverted to Newark to get to portland"

Pros: "Good"

Cons: "Never made it so I can't rate it"

Pros: "Everything went smoothly"

Pros: "Large plane very comfortable"
Cons: "Nothing"

Pros: "There was a large amount of room"
Cons: "NA"

Pros: "Staff was great"
Cons: "Second delay in a row"

Cons: "Delays both ways"

Pros: "Everything!"

Pros: "Smoothly and on time"

Cons: "Fine until the unexpected stop but has to be done"

Pros: "Very respectful and loved all the smiling facez"
Cons: "N/A"

Pros: "Excellent choices, comparisons, easy to use, updates"

Pros: "Bigger planes"

Pros: "On time."

Cons: "Prices to watch Tv"

Pros: "All went as planned"
Cons: "Coffee"

Pros: "American Airlines saved the day!"

Pros: "Excellent"

Pros: "On time"

Read more about Alaska Airlines
COVID-19 information

Safety measures for airlines flying from Chicago to San Luis Obispo

Airlines flying from Chicago to San Luis Obispo have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to San Luis Obispo

Mandatory masks

Masks required on board, masks provided on flights from Chicago to San Luis Obispo

Social distancing seating

Middle seats unavailable to book on flights from Chicago to San Luis Obispo

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to San Luis Obispo

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