Find cheap flights from San Luis Obispo to Chicago

SBP - CHI

Find cheap flights from San Luis Obispo to Chicago

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Round-trip
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San Luis Obispo (SBP)
Chicago All airports
Thu 4/15
Thu 4/22
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Good to know

Low season

JulyBest time to beat the crowds with an average 19% drop in price.

High season

JuneMost popular time to fly with an average 12% increase in price.

Average price round-trip

$401(avg. price over the last 2 weeks)

Good deal round-trip

$257or less

Good deal one-way

$186or less

Book cheap flights from San Luis Obispo to Chicago

When to book flights from San Luis Obispo to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $186 or less one-way and $257 or less round-trip.
  • The cheapest flight from San Luis Obispo to Chicago was found 30 days before departure, on average.
  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is July.
  • Morning departure is around 12% 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

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Top 3 airlines serving San Luis Obispo County to Chicago

Scores according to KAYAK customer reviews

8.3
Alaska Airlines
Overall score based on 29,316 reviews
8.5
Boarding
8.3
Comfort
8.8
Crew
7.9
Entertainment
7.9
Food
Airline reviews

Pros: "Love the entertainment options with my own device, food, and power at the seat"
Cons: "Entertainment was disrupted. Departure was delayed by delayed departure of the previous flight without enough explanation to those of us waiting to board"

Pros: "Movie options and healthy food"

Pros: "The crew"
Cons: "Communication with delays and seat changes when planes change."

Pros: "The cheese and fruit tray is great."
Cons: "Boarding takes forever. The seats are too narrow."

Cons: "The food options"

Pros: "Boarding and in boarding took forever and the leg room was damn cramped but it was good overall"

Pros: "Awesome crew"

Cons: "There was grease under the seat in front which has ruined my shoes. They have to be thrown out now. Very unhappy with this outcome."

Pros: "Direct flight"
Cons: "N/A"

Pros: "Good timing"
Cons: "All went well"

Pros: "Love that they have free movie choices and free earphones. Also, loved the menu for drinks and food!"

Pros: "Short lines, efficient service, most of all kind staff all the way from the counter attendants to the pilots."

Cons: "We were delayed for 40 min and had a last minute gate change"

Pros: "Seats are comfortable and feel roomier than most, boarding was easy, flight was turbulant but still comfortable and even arrived early, fantastic crew, never have an issue."
Cons: "The following are not complaints just my review of the topics given: I did not purchase any food on my Alaska flights because there were no plant based (vegan) options. I was unable to use the in-flight entertainment that was advertised (many times) for unknown reasons."

Cons: "Flight was delayed"

Pros: "On time"

Cons: "Great crew! Smooth flight. Need more hot options for food"

Pros: "Arrived on time. Nice staff. Good sandwich."
Cons: "Everything good."

Pros: "All good with Alaska and Virgin America"

Pros: "Great crew. Boarding process."

Cons: "No free food was offered. Movies were not free."

Pros: "timeliness, courteous, comfortable, charging outlets at every seat."
Cons: "weak movie selection"

Pros: "Pleasant attendants"
Cons: "All good"

Pros: "I liked the food options and the entertainment. Staff was really friendly too,"

Pros: "On time."
Cons: "Slow boarding and deplaning."

Pros: "Fruit platter. On time. Efficient. Professional Plane was very clean"
Cons: "Seattle airport first security man grumpy. Not helpful. No reflection on Alaska airlines however"

Pros: "Friendly crew, clean plane, loved that there was USB and power outlets in every seat, on time departure and arrival"

Pros: "The crew is consistently on point ! Accomadating , friendly and warm !"

Pros: "Friendly cabin crew, wonderful food, spacious aircraft, wonderful option to get a tablet to watch a movie. Loved being able to plug in at each seat with USB charger etc."

Pros: "Boarding was efficient, seat was comfortable. I appreciate that food and drinks were offered often."
Cons: "One particular flight attendant purposely ignored me when I tried to ask for cream and sugar for my coffee which she did not offer when handing out drinks. Then she looked right at me twice as I tried to give her my garbage which she was collecting, but she ignored me again and left me holding my garbage until a different flight attendant came much later and took it without incident. It made me wonder if it was because I looked Asian- she was helpful and polite to the white women next to me. I was polite and was not being difficult in any way. I'm half white, but was often treated like this in Illinois when I was growing up. She should have been professional and if she had I would have rated the trip as excellent."

Pros: "Was in time. Leg space was good"

Pros: "nice helpful employees. On time service."
Cons: "nothing"

Pros: "Seats are a little larger n more legroom for my 6'2" big man of a husband"

Pros: "Your typical airlines for check-in, baggage etc but I was pleasantly surprised when our seat assignments were together for the return trip w/out having to select them. Baggage was extremely fast on the outbound flight but took a few minutes on the return flight."
Cons: "Again, as with most airlines, the seating room leaves a little bit to be desired but the leg room was adequate for a 6'4" man."

Pros: "I've always had a good experience with Alaska Air."

Pros: "Plenty of overhead bin space; no excessive announcements; ultra clean cabin; flight deck explained the lengthy ORD taxi time to the arrival gate"
Cons: "FA's appeared to be rushed during boarding. I was asked to put up my tray table, and I spilled all of my French fries on the floor as the flight attendant watched. I had to leave the mess all over the floor. My seat neighbor offered to help clean the mess. I cleaned it up on my own with a safety information card as a scoop and dumped the mess into a puke bag. The flight attendant should have offered a trash bag as there was plenty of time before takeoff. I flew for your airline as a flight attendant for almost four years, and I know AS flight attendants are among the best."

Pros: "I liked the choices of food and the movies!"
Cons: "I thought it took too long to get the laptops out. I didn't finish my movie."

Cons: "Seating felt a little more cramped than usual."

Cons: "Wondering why a very intoxicated man was asked to sit next to me. He had two deep cuts in his fingers, couldn't focus on sitting down, awful hygiene, was sold two vodka cocktails, and he hit his eye on the straw because he fell to sleep then woke up to drink more. I felt very uncomfortable throughout the entire flight and would like to speak with someone from Alaska Airlines."

Pros: "I like a lot the treatment"

Cons: "I requested an aisle seat because I have broad shoulders and a knee that hurts if I can't extend it. EVERY TIME a particular stewardess would pass, she'd SLAM into my shoulder, with no care or apology. This was very hard to enjoy a drink, or sleep, or do anything on the flight."

Pros: "easy check in. (emergency seat with no extra cost) kind staff. board on time. but not declined seat, new plane with two power outlet."

Cons: "See above."

Pros: "Wonderful seat and attendants."

Pros: "Straightforward. Love that Starbucks coffee is offered! Also love that you can charge devices. The inflight entertainment option works for me; I usually come prepared but I was happy to pay to watch a movie, although the cost seemed unnecessarily high."
Cons: "There was quite a bit of wait at boarding time while standby seating was sorted out. I wasn't sure why ticketed customers could not board on schedule; instead, everyone was standing around at the scheduled board time while names were announced, etc."

Pros: "I have become a major fan of Alaska Airlines. Check In is so easy, the attendants are friendly, the food is worth purchasing (although a bit too spicy for me), the choices of flight times is impressive. I have flown with Alaska three times in the past year and every flight was booked solid. Must be lots of others who feel the same way I do."

Pros: "Having an exit row"

Pros: "Seats, beer selection, very friendly staff I will be flying again if I get the chance and I never say that anymore about other carriers."

Pros: "On time"
Cons: "Nathing"

Pros: "All good, except poor prep on food"
Cons: "As above"

Pros: "Not much"
Cons: "Seating horrible"

Cons: "gate assignment took too long"

Pros: "It is good"

Cons: "No tv on seat. Those dumb comedy tv show"

Pros: "How spacious it felt and there were film selections"
Cons: "My film kept stopping randomly."

Cons: "The boarding experience is awful. I wish that there was more order to the boarding process such as with Southwest Airlines. There is simply no control over rude passengers who push there way to the front."

Pros: "at least flights were on time. 20 minutes delay is not bad."

Pros: "Nothing."
Cons: "Cramped, claustrophobic space. Cabin too warm."

Pros: "It was very inexpensive and on time. And it was much more comfortable than those budget airlines like Spirit, Frontier, etc."
Cons: "The snack choice was unappealing."

Cons: "The touch-screen entertainment system was not very responsive. It was difficult to get the screen to recognize your selection."

Pros: "Aircraft comfort and entertainment options"

Pros: "I like it! Thank you, kayak"

Pros: "Friendly and prompt service."

Pros: "personal entertainment systems and charging plugs"
Cons: "only pretzels and no headphones offered for the entertainment systems."

Cons: "Aircraft need to be updated. Or price should be credited when you get such an old aircraft."

Pros: "Entertainment and great beverage options"

Pros: "Seat were comfortable and I didn't feel claustrophobic."

Pros: "Todo muy bueno"

Pros: "The staff was friendly and helpful"
Cons: "There was a ton of turbulence"

Cons: "Boarding late"

Pros: "Friendly staff Smooth ride On time"

Cons: "Always delayed"

Pros: "NOTHING"
Cons: "Everything. DELAYS___DELAYS"

Pros: "Pretty comfortable"

Pros: "On time."

Cons: "Got cancelled"

Cons: "I am still not feeling well to travel, so I was staying at home and no Madrid, may be in the fall or winter when I get better, I will visit Madrid one more time."

Pros: "very smooth, ontime ride.. kool"
Cons: "everything was ok"

Pros: "Delays caused a little stress but all in all a good experience."
Cons: "Late arrival to DCA."

Pros: "The TIMING AND ATMOSPHERE"

Pros: "Upon sitting down, I was able to fall asleep almost instantly. The helpful stewardesses were constantly aware of my needs."
Cons: "Check-in desk seemed confused and unorganized. Two very friendly ladies were helping out but were on different wavelengths."

Cons: "Numerous delays and disappointments. Two delays before boarding. Another long delay after boarding waiting for paperwork to be completed. Long taxi period. Waited over half hour for baggage claim conveyor to start rolling."

Pros: "Very professional"
Cons: "We didn't leave on time"

Pros: "Everyone was gracious and very helpful. Wheel chairs waiting at each stop. Special ramp installed at CHO, VERY HELPFUL."

Cons: "EXTREMELY LONG CHECK IN & SECURITY LINES"

Pros: "On time arrival despite two issues at the departure gate"

Pros: "Service, comfort, timeliness."
Cons: "Food was marginal, especially the chicken in the salad, which was petrified."

Pros: "It was fine. I was comfortable and I slept throat most of it."

Pros: "Not much"
Cons: "We sat on the tarmac for an hour after we landed. Missed my connection, no other flights that night. It wasn't even 10 pm yet."

Pros: "Everything was very professional."

Cons: "90 min late"

Pros: "A breakfast offering at any time would be great."
Cons: "Too many people getting on at same time."

Pros: "Boarding was smooth"
Cons: "It was fine"

Pros: "Good"

Pros: "Roomy & comfortable seating for such a small aircraft"
Cons: "Late boarding, over an hour"

Cons: "Gate changed and baoarding time changed countless times."

Cons: "No tv."

Pros: "Both planes were delayed"
Cons: "I did not appreciated getting to my destination so late."

Pros: "This was ok"

Pros: "Easy process with no delays"

Pros: "All was well"
Cons: "I had no real complaints"

Pros: "you guys have tvs in the headrest and its spacious in the seating area. you all treated me way better than spirit airlines!"

Pros: "All good"

Pros: "Nothing"
Cons: "Turbulence"

Pros: "Great service. Free Internet and movi9"
Cons: "Seat next to the restroom"

Pros: "Cleanliness of plane"

Pros: "Great staff. Great safety explanation. Smooth fight"
Cons: "Nothing. Everything was great. I'll definitely try to stick with united for my future travels"

Pros: "arrived on time despite delayed departure"

Cons: "Left about 15 minutes late. But we didn't miss any connections so everything turned out okay."

Pros: "Polite staff"

Pros: "Flights was ontime"
Cons: "Plane was too hot, and then way to cold. This seems to be a re-occurring problem. I am not sure why the plane can't just be set to be be 68-72 degrees. There is no need for it to be above 80 or less than 60."

Pros: "Price was lowest for that date and itinerary."
Cons: "Feels like United is second class compared to other carriers. I purchased this for my Morher-n-Law who rarely flies was traveling by herself. there were 7 gate changes 3 day of. I Was very concerned if she would make it."

Pros: "Lots of turbulence"

Cons: "Delayed three times"

Pros: "Nice plane for a small one"
Cons: "Bumpy ride."

Cons: "Two time delayed"

Pros: "Polite and pleasant attendants"
Cons: "nothing"

Cons: "My luggage did not make it to my destination."

Pros: "Constant updates by email. Very informative"
Cons: "Nothing"

Pros: "On time, boarded quickly, checked my carry on all the way through Tampa for me"

Pros: "The price"
Cons: "I was unable to board because I didn't see the boarding time. This should be available even if it is just an estimated time. This way if I am running late I know what time I have to be there."

Cons: "Departure from Chicago was delayed"

Cons: "The very very long delay"

Pros: "Everything went smooth"

Pros: "Check-staff was very gracious."

Pros: "No problems"
Cons: "Little bumpy but bad weather"

Pros: "Friendly service, nice and comfortable."

Pros: "Food was good"
Cons: "Dinner was served within 1 hr of takeoff and breakfast 1-2 hrs of landing. Nothing served inbetween. There was about 10-11 hrs of nothing. No drinks or snacks served. Very poor service in compairison to other international flights I have taken."

Pros: "Staff was very nice"
Cons: "Two flights, two delays."

Cons: "I cancelled it and it appears it didn't really cancel"

Pros: ". We got back 30minutes early then schedule!"

Pros: "Pilot got is there 25 min early"

Pros: "Cost Ease of booking"
Cons: "delays (weather based )"

Pros: "On time."

Pros: "Everything else was fine"
Cons: "Not a lot of smiles"

Pros: "Still deciding"
Cons: "All flights were late."

Pros: "Quick check in!"

Cons: "Delayes"

Pros: "Trip was on time and a good experience overall."
Cons: "No Coffee"

Cons: "Lack of comfortable space. :-("

Pros: "I like the complementary soda. The boarding groups system is smart."
Cons: "I don't care for the wifi options. Loud children."

Pros: "Excellent"

Pros: "On time"

Pros: "As pleasant as possible."
Cons: "Nothing negative to note."

Pros: "Attendant was attentive to her job."
Cons: "The aircraft is uncomfortable."

Pros: ".The attendant was caring and efficient."
Cons: "The boarding process seems to be a cluster of misguided sheep. The aircraft is uncomfortable even for us thinner patrons."

Cons: "The plane was just small and I'm a big guy."

Pros: "I was so comfortable and I got to sleep"

Pros: "Very friendly and great service. Gave us drinks twice."

Read more about Alaska Airlines
COVID-19 information

Safety measures for airlines flying from San Luis Obispo to Chicago

Airlines flying from San Luis Obispo to Chicago 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 San Luis Obispo to Chicago

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Book cheap flights from San Luis Obispo to Chicago

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