Find cheap flights from Chicago to San José

CHI - SJO

Find cheap flights from Chicago to San José

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Round-trip
Economy
Chicago (CHI)
San José Juan Santamaria Intl
Fri 4/9
Fri 4/16
Any month
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Good to know

Low season

SeptemberBest time to beat the crowds with an average 15% drop in price.

High season

DecemberMost popular time to fly with an average 36% increase in price.

Average price round-trip

$413(avg. price over the last 2 weeks)

Good deal round-trip

$334or less

Good deal one-way

$152or less

Book cheap flights from Chicago to San José

When to book flights from Chicago to San José

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 $152 or less one-way and $334 or less round-trip.
  • The cheapest flight from Chicago to San José was found 52 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is September.
  • Morning departure is around 7% 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 flights from Chicago to San José

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Top 3 airlines serving Chicago to San José Juan Santamaria Intl

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,138 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "The entertainment options are good as well as free messaging on wifi"
Cons: "The boarding was late, the take off was late (weather), then arriving in rdu was delayed because the bridge was broken. All around, I’ve had better experiences but I’ve had much worse on SW."

Pros: "FA were ok"
Cons: "No entertainment"

Pros: "The crew was amazing"
Cons: "Other travellers where rude"

Cons: "Wifi didn't work"

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Pros: "The crew was awesome. The entertainment was great with a huge selection of movies. The food was really good."
Cons: "Boarding was delayed while waiting for Delta agents to come and assist people off of the plane."

Cons: "Let was a typical flight. About all you can hope for is that it is on time. That makes it excellent."

Cons: "Great flight. On time and friendly staff."

Pros: "Amazing crew, on time, decent coffee, plenty of drinks"
Cons: "The drinks cart was a little slow..."

Cons: "Seating was cramped in economy, but you get what you pay for!"

Pros: "Smooth flight."
Cons: "Tight seat. Small space."

Pros: "Yravelling goes well when workers are competent and organized."
Cons: "Boarding front to back seems counterintuitive. People carrying 2 bags appear more hassled bumping through people to get to their seats further. Ack"

Cons: "Couldn't believe the flight attendant walked around with a tray of snacks and bananas. When I asked for the banana, she said, "Oh I'm sorry, those are for First Class only". Really?"

Pros: "Free messaging during flight was REALLY nice!!! Smooth flight, early arrival, good coffee, variety of drinks, entertainment system worked very well and fast."
Cons: "Seat bottom cushion was not comfortable, also I think my seat was broken as any time I leaned forward it returned to upright position. Food was good but need more snack for a long haul flight. Needed more drink offers between meals."

Cons: "At least one hour late"

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Pros: "Not comfortable and not helpful"
Cons: "Some rude staffs , not helpful"

Pros: "Flight was on time and arrived a little early."
Cons: "I was seated next to a very large man (6’5” he said) and had no room in my seat. Thankfully the seats in front of us were empty and the flight attendant moved him."

Cons: "Crew was grumpy and Curt. Seats still smaller than a kindergarten class, and didn't even serve water."

Pros: "Everything went smoothly - very happy"

Pros: "Delta planes are typically nice and clean"
Cons: "Flight was delayed multiple times."

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "Weather kept them from being able to serve everyone but she did pass around cookies which was a really nice thought!"

Pros: "Everything escept the seat that was too small. I also had problems with the entertainment when trying to see movies."
Cons: "Seats too small ant could not watch Movies beacause the screen was defective."

Cons: "You messed up my life with your poor service."

Pros: "Equipment was nice and well maintained. Seats are comfortable for coach. Video at each seat. Friendly staff."

Pros: "The staff really helped me out getting on standby so that I didn't have to wait for a 9 hour layover. Overall great experience and great staff."

Pros: "Had to cross terminals and the pathway was closed due to an international flight landing (poor planning on LAX part) so had to exit and reenter terminal through TSA. Flight delayed an hour then cancelled due to control panel failure. 10pm flight became 12am bus (and originally told it was 11.15pm bus which was "stuck in traffic" when google map traffic was all green). Got back to SD 4 hours after scheduled time."

Pros: "There were alot of good movies to choose from, and the food wasn't bad."
Cons: "It's always very uncomfortable to sit on a plane for a long time, but that's nobody's fault"

Pros: "On time. Good customer service. Easy route, no hassles."

Cons: "Kids yelling"

Pros: "Delayed and told die to Air Traffic Cintrol with ninproxtove means to resolve our delay. Poor customer sefvie at JFK...indifferent and lied to us."

Cons: "The flight crew and staff were all great!"

Pros: "Great service and amenities for a low cost"
Cons: "Nothing"

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "plane had individual movies for free with each seat!"

Pros: "Entertainment options"

Cons: "Flight was 7 hours delayed and every 2 hours of waiting they delayed the flight 2 more hours"

Pros: "Excellent service and on-time"
Cons: "Baggage charge"

Pros: "I felt the entire flight crew was there to make my trip more pleasant. The plane was new and had free video and usb outlets to charge my devices."
Cons: "Nothing, truly an excellent experience."

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "Flight left on time despite the problems"
Cons: "We waited for one hour to be able to board. The system crashed so we were very lucky to arrive very early to the airport"

Pros: "Same as previous flight."

Pros: "Some entertaining choices but not all clear which ones were in my flight"
Cons: "The food I wanted had sold out by the time I ordered it"

Cons: "Food"

Pros: "The quiet so I could sleep"
Cons: "Changing my seat last minute. Had to ask two women to move to get into my seat. Loading the plane first with passengers that have nothing to store above would expedite the experience for me. My seat belt disconnected from the back of the seat. The tray was broken and could not be lowered into a writing or eating position."

Pros: "The staff of Dekta were welcoming as well as helpful. The flight was professionally run and I enjoyed it."
Cons: "The auxiliary power went down before we took off. However, the flight captain assured passengers that procedures would be followed to assure our safety. We waited on the plane for 10 minutes and then took off. Thanks to staff for following safety procedures."

Pros: "Flight, plane, and crew were great."
Cons: "MEX customs was a nightmare."

Pros: "Very communicative about things like bathrooms being closed for sanitation, turbulence etc."

Pros: "Nothing. There were no Covid-19 measures in place and no social distancing. Unsafe. Crew without masks."
Cons: "FOLLOW COVID-19 TRAVEL GUIDELINES!!!"

Pros: "The crew was great"
Cons: "The disappointing issues were with the airport process."

Cons: "I didn’t like that the flight had a 4 hour delay!"

Pros: "The food is terrible no choices you can tell nothing is fresh they did not even have enough white wine"

Pros: "Nothing in particular"
Cons: "A more organized boarding process"

Pros: "Crew was good, food was good."
Cons: "The entertainment, I saw the Wifi stuff when I bought the ticket, but there was no internet connection there. Besides, no movies, no screen... boring."

Cons: "Be in time, over 1 hr delayed."

Pros: "Good food"
Cons: "Ground staff need tourist training"

Cons: "Terrible crew on this flight."

Pros: "The large plane that I was on was great. Comfortable and a smooth ride. Movies were good. Drinks good."
Cons: "Food could be a little better."

Cons: "Over booked"

Pros: "We arrived at our destination eventually."
Cons: "Probably one of the most tedious flights of my life. Unexplained delays while sitting on the tarmac and not allowed to get up to go the bathroom because “we could be leaving any minute”. Repeated indications that we were cleared to move, and then no movement for another 15 minutes before assuring us they were cleared to move. Everything about this airline, from check-in to boarding to taxiing to deplaning to baggage claim felt like it took 60-80% longer than it had to, with no real customer service to be found. This is an airline that does nothing more than provide passengers with a way of getting from point A to point B, eventually; getting there on time, or in comfort, was clearly a luxury their airline was not positioned to deliver. First and last time flying Aeromexico, especially with Internet, Volaris, and other carriers plowing the same routes."

Cons: "Did not get the sense that check-in staff was terribly concerned about getting us checked in quickly."

Pros: "Luggage was found that was good"
Cons: "Horrible day nobody here to guide you or help you and then charge you an arm and a leg."

Pros: "Flight on time, all personal was very helpful and kind"
Cons: "No choices for breakfast and the one served on first class not so great."

Cons: "Will not travel with this airline again"

Pros: "Ease in ticketing."
Cons: "The hardest part was the long layover. I didn’t dress warmly enough, so I had to keep moving!"

Pros: "Servicio. Puntualidad."
Cons: "Todo bien"

Pros: "Food, entertainment, leg room much better than any US airline. Crew is smart and efficient."

Cons: "Your customer service center is useless. The representatives do not help, they are mean and patientless."

Pros: "The crew at the gate did their best to seat my family together."
Cons: "No entrainment available and the flight crew took over an hour to bring me some water."

Pros: "I would like to have direct flight to Mexico city, it will be a plus."

Pros: "Good flight, on time, efficient boarding and crew."
Cons: "Our seats were next to emergency exit, didn't recline and the person infront reducer my space when reclined fer seat back."

Cons: "Rough Landing"

Pros: "Glad it was on time. Everything was great"

Pros: "Vuelo acorde con el horario establecido"
Cons: "Regular atención del personal en el aeropuerto"

Pros: "Amazing service, clean plane, complimentary food and drink included is a great perk. Too bad other airlines don't treat you this well! My first choice for all future flights to Mexico. Gracias AeroMexico."

Cons: "Crew standing in the back talking to each other with their backs on us"

Cons: "El vuelo es helado. Es tarde en la noche y sin mantas!"

Pros: "Close for connecting and had lots of staff to get you there on time."
Cons: "Food mediocre"

Pros: "The in flight meal was just what we needed and they got us to San Jose safe and sound. No complaints!"

Pros: "Ontime and pleasant"
Cons: "Food"

Pros: "Lots of really good movie choices"

Pros: "It was a direct flight."
Cons: "The delay when departing, and the attention of the flight attendants. Also very limited kind of beverages."

Pros: "La comodidad la amabilidad de las personas."
Cons: "La comida"

Pros: "Nothing. We’re not there yet"
Cons: "Everything. AM customer service is beyond horrible and unhelpful."

Pros: "I liked the service and the food that was provided."
Cons: "My suitcase was ripped on the back"

Pros: "Good selection of movies which are controlled by the individual passengers. Comfortable seats. Served breakfast of fruit, yogurt and muffin."
Cons: "Don't like flying through Mexico City because the immigration process is very poor, i.e.long lines to get to agents . Airport is cold at night."

Cons: "My flight was changed. I received no notification. Representative did not care that about my needs. Will never fly with them again."

Pros: "5 stars to the supervisor Octavio"
Cons: "The rest of the Team do not know what customer service is"

Pros: "Flight is on time"
Cons: "Everrything was ok"

Pros: "The snack - such as it is - is certainly a step above what I get when I fly the same route on United. Also the entertainment system is much better, and free! Cabin staff are friendly and efficient. The seating is about the same as on every other airline. I was in steerage for the Mexico City - San Jose leg. A lady was seated in my window seat when I boarded, and seemed surprised when I insisted on reclaiming my seat (She had the middle seat). In contrast to Mexico City, the San Jose airport is a model of efficiency. Immigration is rapid, luggage comes out on the carousel in good time, and best of all there is a duty free shop right in the luggage claim area, so it is unnecessary to buy liquor ahead of time."
Cons: "Mexico City is a terrible airport to have to pass through. Everyone has to go through Immigration (similar to US airports in that regard) even if just in transit. However, they have few officers there, and almost half of the available booths weren't even manned. The result was chaos, with the immigration hall filled with grouchy travellers, and other travellers stuck in aircraft waiting to disembark. Expect to be stuck in Immigration for a minimum of an hour after landing; maybe plan on 1 1/2 hours just to get through Immigration and Customs. And if you are making a connection, whatever you do don't go through the sliding doors on the other side of Customs - I made that mistake once! I speak Spanish, so the following comments are not coloured by language difficulties ... Security staff are unfriendly. While there is supposed to be free wifi in the departure lounge, I couldn't figure out how to use it. A gate agent told me there wasn't any free wifi, all the time standing beside a sign that said there was. I was also singled out for a spot check of my hand luggage right in the jetway. The unfriendly lady doing that search so disarranged my stuff that I couldn't find my Kindle when I got on the plane, so was without my planned reading material."

Cons: "Everything worked well"

Pros: "Everything. Everybody very helpful"

Pros: "Un pequeño retraso a la salía de México, sin mayores inconvenientes"

Pros: "I was impressed and very happy the flight was early. I had low expectations with Aeromexico because in the past every flight I took with you was delayed or late."

Cons: "The thing I did not like is that I call Aeromexico to pay for the extra loggage tha I had before my fly and the person that I talk to told me that everything was all paid for and when I got to the airport guess what, The extra luggage was not paid so they charge a lot more than what I would have paid the first time a call."

Pros: "Great selection of movies to watch"
Cons: "The crew seemed to be in a bad mood that night. One of the flight attendants hit my elbow as he was speeding through the aisle, causing me to knock over my drink. He didn't apologize or try to help. The other one"

Pros: "Price"

Pros: "My bag came out really fast. Boarding on and off was a breeze."
Cons: "Paying for baggage when I could have just carried on."

Pros: "Nothing"
Cons: "I was trying to save money for the church , but it cost me more then I had budget for"

Cons: "Fee for baggage is ridiculous. Fee for baggage is ridiculous. Fee for baggage is ridiculous."

Cons: "Check in staff was very unprofessional. 3 delays!"

Pros: "Traveling with friends"
Cons: "Add on charges!"

Pros: "Seat 3D was larger size seat"
Cons: "Idiots seating behind me were loud"

Pros: "Everything was good"
Cons: "Everything was good"

Pros: "seat more comfortable than most airlines"

Cons: "... and they charge a penalty if you go to their counter first without going first to the check-in kiosk? Cheaper, sure, but totally lacks class"

Pros: "Cheap fare"
Cons: "Expensive bag check fees of $52 across the board, even though signs listed a variable scale based on weight that would have been cheaper. Apparently that's only available if you check in early and weigh your bags yourself or something, IDK..."

Pros: "If your looking for a cheap affordable means of flying then spirit is the perfect option."
Cons: "Spirit does not have many options per day, on average only one or two to each destination so your options are limited. They do not give you the ability to have your boarding pass emailed to you, you can only access it directly from their website. And your almost guaranteed to arrive at your destination later than expected because their flights are so often delayed."

Pros: "The 45 minutes before boarding line is genius but..."
Cons: "...the guy at the desk was a jerk. Get employs that don't roll their eyes when they're doing they're job."

Pros: "Reshedule"
Cons: "Poor services"

Cons: "Late boarding, lack of communication, terrible seat that did not recline"

Cons: "Spirit airlines employees are not friendly and difficult to deal with. Were not accommodating"

Pros: "Nothing"
Cons: "Everything"

Cons: "Spirit does not participate in TSA Precheck"

Cons: "Delayed for no reason"

Pros: "Arrived in one piece."
Cons: "Seat space nonexistent and they can't move back."

Pros: "We did opt for extra leg room with an added charge."

Cons: "Delay to taxi down but the rest was good"

Pros: "Free upgrade to emergency row."
Cons: "Nothing."

Pros: "Liquor, cat boarding on plane."
Cons: "Someone threw up. Had to switch flights"

Pros: "Luckily sitting by good people"
Cons: "Beer was warm and $7"

Cons: "My luggage was damaged"

Pros: "The plane looked brand new! Plenty of room! Friendly staff! We could even understand and hear the safety instructions! (Yes, even after flying several times I still pay attention to them.)"

Pros: "I didn't like anything"

Pros: "Nothing"

Pros: "Comfort"
Cons: "People"

Pros: "Cheap"
Cons: "Solicitation for credit card"

Pros: "Nothing"
Cons: "I didn't like anything"

Pros: "Nothing"

Pros: "They were able to switch us to emergency row seating."
Cons: "Too expensive for everything. No room at all for anything. Super uncomfortable"

Cons: "It was delayed so long that they canceled it"

Cons: "NO TSA PRECHECK"

Pros: "I love everything"

Pros: "It's was late"
Cons: "Sprit counter employee are very rude"

Cons: "It was cancelled."

Pros: "We made it in 1hr and 15minuted"
Cons: "No room to stretch. Very close to others which is very uncomfortable."

Cons: "They lost $1500 of music gear of mine!!"

Pros: "Very cheap way to go if you don't have luggage to check. And if you bring your own snacks!"
Cons: "My seat and another passenger's seat were both double booked! Never seen that happen before."

Cons: "Ridiculous baggage charges. Paying to get a seat assigned? Really, doesn't the ticket price include that. Low cost mantra is a farce when all costs are considered."

Cons: "See above"

Pros: "Nothing"
Cons: "Everything"

Pros: "The price of the ticket or fare"
Cons: "Unable to pay for my bank online. Then had to pay a higher fee at the airport"

Cons: "delayed"

Pros: "Price was good and everyone was friendly"
Cons: "No room to move"

Pros: "The Spirit woman at check in walked me and several older women through the new security check @ OHare. She helped us to simplify the process."
Cons: "Nothing"

Pros: "Good"
Cons: "Every thing is very good"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago to San José

Airlines flying from Chicago to San José 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 José

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Chicago to San José

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to San José

Book cheap flights from Chicago to San José

Recent round-trip flight deals

4/14
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Spirit Airlines
6h 34m
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Spirit Airlines
17h 34m
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Recent one-way flight deals

5/1
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1 stop
Spirit Airlines
6h 34m
ORD - SJO
5/4
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16h 59m
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Delta
17h 42m
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