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Planning a trip from Chicago to San José? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
| Low season | October |
|---|---|
| High season | March |
| Cheapest flight | $94 |
Direct departures
Chicago to San José Juan Santamaria Intl
Monday
American Airlines, United Airlines
American Airlines, United Airlines
Tuesday
American Airlines, United Airlines
American Airlines, United Airlines
Wednesday
American Airlines, United Airlines
American Airlines, United Airlines
Thursday
American Airlines, United Airlines
American Airlines, United Airlines
Friday
American Airlines, United Airlines
American Airlines, United Airlines
Saturday
American Airlines, United Airlines
American Airlines, United Airlines
Sunday
American Airlines, United Airlines
American Airlines, United Airlines
Direct returns
San José Juan Santamaria Intl to Chicago
Monday
American Airlines, United Airlines
American Airlines, United Airlines
Tuesday
American Airlines, United Airlines
American Airlines, United Airlines
Wednesday
American Airlines, United Airlines
American Airlines, United Airlines
Thursday
American Airlines, United Airlines
American Airlines, United Airlines
Friday
American Airlines, United Airlines
American Airlines, United Airlines
Saturday
American Airlines, United Airlines
American Airlines, United Airlines
Sunday
American Airlines, United Airlines
American Airlines, United Airlines
No delays and arrived to destination 30 min early. Staff was super friendly.
No delays and arrived to destination 30 min early. Staff was super friendly.
San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.
It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.
Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight
Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.
Everything a cheap airline should be at normal airline rates.
Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.
Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.
Full cans of soda would be nice. A choice between two snacks would be appreciated.
Tried watching free movie and it kept freezing so I couldn’t finish.
Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane
I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.
Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.
Great experience with a crew always thinking in the passenger
The flighr attandants were very rude they ignored me didnt offer me anything to drink throughoit the 4 hour flight i feel i was targeted and ignored because i was a darkskin latino man.
I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.
Very happy with my flight. I would definitely recommend it.
Did upgrade, travel in business it was great (more room I could sleep)
We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.
We had a five hour layover in the way home from Colombia. I read the "bout your flight" email carefully before we checked bags. We had to go through security right at the gate. Almost lost our ground coffee because that airport only allows 16 ounce of coffee and we had 18. I've been to 48 countries and never heard of a coffee restriction. I can't follow a rule I don't know about. I requested they bring our coffee to our checked luggage. Instead tey gate checked our bag for free. Back to planning transfers in Dallas I guess
Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.
Always wish for more healthy, gluten free options. We have to bring our own.
Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.
Other than a way way too cold cabinets for the entire flight, all was great
One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.
My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.
Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.
Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.
I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion
The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.
We loved the steward on the plane. He made the night enjoyable
The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.
My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.
Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes
3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!
After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"
After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.
Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan
I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.
I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude
Endless, trip oof my life, we still are in in plane waiting for getting off.after 3 hours delay. Not even a glass of water.
It was cheap. Spirit is what it is. I got to my destination and home safely. There was no food or entertainment without paying extra, which is fine. That’s why the flight was inexpensive.
Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight
No leg room. My knee was sore for a day.
It was better than expected. But there were two delays in taking off.
To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.
The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.
Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.
Flight was delayed. (To be excepted because of TSA shortage) I’m super short and still struggled with leg room, there was no screen, and the seat didn’t recline at all.
The pilot would speak it was painfully load a d the crew had to know this! Maybe the were hesitant to tell him. It was just a mediocre experience and I was in Spirit first class!