Cheap flights from Chicago (CHI) to San Jose (SJO)

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Lowest round trip fares by airline from Chicago and San Jose

Cheapest prices ($174 One Way, $384 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in San Jose

Hotel La Guaria Inn & Suites

Hotel La Guaria Inn & Suites

2.5 out of 5
Alajuela, 2nd. Av., 1st. Street, Del Teatro Municipal 200 m. al Este, Alajuela, Alajuela, 20101
The price is $45 per night from Jul 6 to Jul 7
Stay at this hotel in Alajuela. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the overall value in our reviews. ...
Hotel La Guaria Inn & Suites
Hotel El Maragato

Hotel El Maragato

3 out of 5
Ave Central, between street 1 and 3, San Jose, San Jose
Stay at this 3-star family-friendly hotel in San Jose. Enjoy free WiFi, breakfast, and room service. Our guests praise the helpful staff in our reviews. Popular ...
3.5/5 Good! (2 reviews)
Great hotel if you can handle the street noise.
"I was expecting much worse for the cheap price, but the hotel was very decent. It was clean, had a large bed, a TV, wifi, and AC - amenities that are not always included in a Costa Rican's hotel. Breakfast was poor though. The best part - and the worst - was the location, right on Avenida Central. ..."

Reviewed on Sep 17, 2015

Hotel El Maragato
Hotel Luisiana

Hotel Luisiana

3.5 out of 5
100 west and 400 south from Cruz Roja, Santa Ana, San Jose, 506
The price is $37 per night from Jul 11 to Jul 12
Stay at this 3.5-star golf hotel in Santa Ana. Enjoy free WiFi, breakfast, and a children's pool. Our guests praise the helpful staff and the clean rooms in ...
4/5 Very Good! (6 reviews)
"Pet friendly. I love it"

Reviewed on Dec 18, 2021

Hotel Luisiana
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to San Jose

Origin Chicago
Destination San Jose
Number of Daily Flights
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Latest Flight Departure Date
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Cheap flights from Chicago to San Jose

Costa Rica's capital city is often skipped on trips to Central America, but San Jose has plenty to offer, including an underground Museum of Gold.

If you're coming to San Jose from Chicago, then you'll need to make a stop at another airport on your way. If you fly from O'Hare International Airport (ORD) to Juan Santamaría International Airport (SJO), then your travel time can take anywhere from 7 hours to 20 hours.

Attractions

San Jose is filled with parks and public spaces, including Parque Central, Parque Morazan, and the Plaza de la Cultura under which you will find the Museum of Gold.

To the west, you'll find the Parque Metropolitano La Sabana, a 177-acre expanse of green land that is highlighted by the National Stadium. The Costa Rican Art Museum is also located on the grounds of the park.

Near the University of Costa Rica, you'll find numerous cafes and restaurants, including the Jazz Café which features live music every night.

Hints and Tips

SJO is about ten and a half miles outside the San Jose city center, but you can take a city bus downtown for less than a dollar. Place your luggage in the storage area underneath the bus. This is by far the cheapest option.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.