$162 Cheap JetBlue Airways flights from Chicago to San José (ORD to SJO)

Find The Best Day To Fly from Chicago to San José

Amazing JetBlue Airways ORD to SJO Flight Deals

The cheapest flights to Juan Santamaría Intl. found within the past 7 days were $298 round trip and $162 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 17 - Tue, Sep 23
ORD
Chicago
SJO
San José
$298 Roundtrip, found 1 day ago
$298
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 17 from Chicago to San José, returning Tue, Sep 23, priced at $298 found 1 day ago
Mon, Sep 22 - Thu, Sep 25
ORD
Chicago
SJO
San José
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 22 from Chicago to San José, returning Thu, Sep 25, priced at $305 found 1 day ago
Sat, Sep 6 - Mon, Sep 15
ORD
Chicago
SJO
San José
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Chicago to San José, returning Mon, Sep 15, priced at $329 found 2 days ago
Sat, Sep 13 - Thu, Oct 2
ORD
Chicago
SJO
San José
$339 Roundtrip, found 7 hours ago
$339
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Sat, Sep 13 from Chicago to San José, returning Thu, Oct 2, priced at $339 found 7 hours ago

SJO From ORD Economy Coach Packages on Similar Airlines

Price found within the past 48 hours. Click for updated prices.
Palo Alto Glamping Hotel

Palo Alto Glamping Hotel

4.5 out of 5
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
Namu Garden Hotel & Spa - Adults Only

Namu Garden Hotel & Spa - Adults Only

4.5 out of 5
per person
Sep 19 - Sep 25
found 23 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
The Springs Resort and Spa at Arenal

The Springs Resort and Spa at Arenal

5 out of 5
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
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Frequently asked questions

Can I catch a flight from O'Hare Intl. Airport (ORD) to Juan Santamaria Intl. Airport right now?
It's wise to find out about any quarantine requirements and travel advice reports in place in your destination city. Be sure to visit the Covid-19 Travel Advisor for up-to-date info on catching a flight to Juan Santamaria Intl. Airport from O'Hare Airport.
What terminal is JetBlue Airways at O'Hare Airport?
You should find out exactly which terminal JetBlue Airways leaves from at O'Hare Airport once you receive your ticket. The same applies to information regarding your arrival at SJO. If you can't locate those details, consult your airline.
Are there JetBlue Airways non-stop flights from ORD to SJO?
If you want to fly with JetBlue Airways from O'Hare Airport to Juan Santamaria Intl. Airport, you'll have to make at least one stopover. While you're waiting for your connecting flight, use the time to grab a quick bite or go for a stroll.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Juan Santamaria Intl. Airport (SJO), please visit our Customer Service Portal.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Discover our best JetBlue Airways flight from Chicago ORD to San José SJO 

To find the best deals on flights to Chicago from San José with JetBlue Airways, just enter your travel dates, filter by JetBlue Airways, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Chicago ORD to San José SJO with JetBlue Airways 

If you’re planning a round trip, booking return flights with JetBlue Airways is usually the most cost-effective option. With airfares ranging from $298 to $339, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way JetBlue Airways flights from Chicago ORD to San José SJO 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way JetBlue Airways flight from Chicago to San José costs from $162. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to San José SJO from  Chicago ORD with JetBlue Airways 

To find a cheap JetBlue Airways flight from Chicago ORD to San José SJO, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on JetBlue Airways flights from Chicago ORD to San José SJO 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as September, or if you book a flight with a stopover. 

 

Find nonstop flights from Chicago ORD to San José SJO with JetBlue Airways 

If you’re keen to be on San José soil fast, don’t waste time with a stopover—filter your search results to show direct JetBlue Airways flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for JetBlue Airways flights from Chicago ORD to San José SJO 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to San José SJO from  Chicago ORD with JetBlue Airways on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

JetBlue Airways Airports
Hop on a(n) JetBlue Airways flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
BOSUSALogan Intl.62
JFKUSAJohn F. Kennedy Intl.30
SJUPRILuis Munoz Marin Intl.29
FLLUSAFort Lauderdale - Hollywood Intl.18
MCOUSAOrlando Intl.12
STTVIRCyril E. King11
STXVIRHenry E. Rohlsen9
DCAUSARonald Reagan Washington National7
TPAUSATampa Intl.7
RSWUSASouthwest Florida Intl.6

Travelers ❤️ these 🏨 after their flight to San José

Hampton by Hilton San Jose Airport
Hampton by Hilton San Jose Airport
3 out of 5
Hwy 1 Airport Blvd, Rio Segundo
This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free ...
9/10 Wonderful! (2,274 reviews)
"Very convenient if you landed late at San Jose airport and need an overnight stay. The place is 10 min drive and they have shuttle service from the airport too. Rental car companies like Hertz, etc have their rental offices right across from the hotel so one can have a nice breakfast, pick car and ..."

Reviewed on Jul 10, 2025

Hampton by Hilton San Jose Airport
Courtyard by Marriott San Jose Airport Alajuela
Courtyard by Marriott San Jose Airport Alajuela
3.5 out of 5
Plaza Los Mangos, Radial Francisco J Orlich, Rio Segundo, Alajuela
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
9.2/10 Wonderful! (1,004 reviews)
"Staff was very friendly! Nothing special about the hotel. No continental breakfast. Dinner was average."

Reviewed on Jul 8, 2025

Courtyard by Marriott San Jose Airport Alajuela
Hilton Garden Inn San Jose Airport City Mall
Hilton Garden Inn San Jose Airport City Mall
3.5 out of 5
Francisco J. Orlich Road, Alajuela, Alajuela
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
8.8/10 Excellent! (1,205 reviews)
"The Hilton hotel was nice and nearby the airports mall, and the city Alajuela. The staff were so kind, friendly, and helpful. They were always greeting you and ensuring you were having a great stay. The hotel transportation was very helpful. Mr. Warner was my favorite and is el mejor driver. The ..."

Reviewed on Jul 5, 2025

Hilton Garden Inn San Jose Airport City Mall
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.
*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.