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

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Lowest round trip fares by airline from Chicago and San José

Cheapest prices ($86 One Way, $215 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in San José

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
The price is $42 per night from Oct 2 to Oct 3
per night
Oct 2 - Oct 3
Stay at this hotel in Alajuela. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Juan Santamaría Park and Alajuela Cathedral are located ...
7.8/10 Good! (506 reviews)
"We had a one night stay at this property ahead of an early morning flight. The hotel had everything we needed - comfy beds, air con and fans. It was a simple 20 minute walk to the Malls. They arranged a complimentary transfer to airport at 4am. And we were able to grab some croissants and fruit on ..."

Reviewed on Sep 9, 2023

Hotel La Guaria Inn & Suites
Hotel El Maragato

Hotel El Maragato

3 out of 5
Ave Central, between street 1 and 3, San José, San Jose
Stay at this 3-star family-friendly hotel in San José. Enjoy free WiFi, breakfast, and room service. Popular attractions Plaza de la Cultura and National Theater ...
7.2/10 Good! (462 reviews)
"Very reasonably priced and the location was excellent."

Reviewed on Oct 29, 2019

Hotel El Maragato
Hotel Luisiana

Hotel Luisiana

3.5 out of 5
100 west and 400 south from Cruz Roja, Uruca, San Jose
The price is $69 per night from Sep 30 to Oct 1
per night
Sep 30 - Oct 1
Stay at this 3.5-star family-friendly hotel in Uruca. Enjoy breakfast, a children's pool, and room service. Popular attractions City Place Santa Ana and Business ...
8.2/10 Very Good! (1,000 reviews)
"The people whonwork there are amazing! Everyone was friendly and helpful. Jenny was especially lovely in the restaurant."

Reviewed on Sep 23, 2023

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 José

San José
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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.


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.