$138 Cheap flight deals from Chicago (CHI) to Central Valley (SJO)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Central Valley

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Sep 6 - Tue, Sep 8
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$779 Roundtrip, found 3 days ago
$779
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, Sep 6 from Midway Intl. to Juan Santamaría Intl., returning Tue, Sep 8, priced at $779 found 3 days ago
Sat, Sep 5 - Sat, Sep 12
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$878 Roundtrip, found 1 day ago
$878
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Sep 5 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Sep 12, priced at $878 found 1 day ago

Airfares from $138 One Way, $318 Round Trip from Chicago to Central Valley

Prices starting at $318 for return flights and $138 for one-way flights to Central Valley were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Oct 16 - Sat, Oct 24
ORD
Chicago
SJO
San José
$318 Roundtrip, found 1 hour ago
$318
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Oct 16 from Chicago to San José, returning Sat, Oct 24, priced at $318 found 1 hour ago
Sun, Jan 24 - Fri, Jan 29
ORD
Chicago
SJO
San José
$364 Roundtrip, found 4 days ago
$364
Roundtrip
found 4 days ago
Select United flight, departing Sun, Jan 24 from Chicago to San José, returning Fri, Jan 29, priced at $364 found 4 days ago
Wed, Nov 4 - Wed, Nov 11
ORD
Chicago
SJO
San José
$366 Roundtrip, found 2 days ago
$366
Roundtrip
found 2 days ago
Select Copa flight, departing Wed, Nov 4 from Chicago to San José, returning Wed, Nov 11, priced at $366 found 2 days ago
Wed, Nov 11 - Mon, Nov 16
ORD
Chicago
SJO
San José
$378 Roundtrip, found 1 hour ago
$378
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Nov 11 from Chicago to San José, returning Mon, Nov 16, priced at $378 found 1 hour ago
Sat, Oct 24 - Fri, Oct 30
MDW
Chicago
SJO
San José
$388 Roundtrip, found 1 day ago
$388
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Oct 24 from Chicago to San José, returning Fri, Oct 30, priced at $388 found 1 day ago

Central Valley economy flight packages

Price found within the past 48 hours. Click for updated prices.
Rancho Corcovado Lodge
3.0-star property

Rancho Corcovado Lodge

8.4/10 Very Good! (62 reviews)

Oct 3 - Oct 10

7 night stay

Chicago (ORD) to San José (SJO)

JetBlue Airways • Non-stop • Coach

San José (SJO) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,777, price is now $1,112 per person
$1,112
per person
found 22 hours ago
We stayed in room 20. Awesome view. Close to the office,breakfast and dining room/bar. Because this was low season, not a lot going on. Very quite. We had dinner 2 night with the cheif Sofia. What great meals. We walked into the small town for 3 other dinners. The Managers had very good recommendations. Also very friendly and knowledgeable about the area.

Reviewed on Jun 18, 2026

Vista Suites at Parador
2.5-star property

Vista Suites at Parador

9.6/10 Exceptional! (10 reviews)

Oct 3 - Oct 9

6 night stay

Chicago (ORD) to San José (SJO)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,358, price is now $1,912 per person
$1,912
per person
found 23 hours ago
Site magnifique - nous avons tout aimé, seul désavantage -impossible d’accéder à des restos ou activités extérieurs à l’hôtel sans voiture.

Reviewed on Apr 2, 2026

Xandari Resort And Spa
4.0-star property

Xandari Resort And Spa

9.6/10 Exceptional! (1,001 reviews)

Oct 3 - Oct 10

7 night stay

Chicago (CHI) to San José (SJO)

Southwest Airlines • Non-stop • Coach

San José (SJO) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,406, price is now $1,534 per person
$1,534
per person
found 1 day ago
There isn't a tv, or phone inside of the room. They only provided a hand and face towel for one person although there were two people on the reservation. The staff knew very little English and offered no real assistance. This is a very misleading resort. Do not listen to social media post dating this is a great resort. Luckily, we only stayed one night to be closer to the airport. The jacuzzi was very cold...not heated like stated. The highlight was the two earthquakes we experienced during the stay.

Reviewed on Aug 24, 2026

Don't see what you're looking for?
See all available trips from Chicago to Central Valley
View all trips

Central Valley packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Noah's Forest by Tifakara
4.5-star property

Noah's Forest by Tifakara

9.8/10 Exceptional! (428 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to San José (SJO)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $1,985, price is now $1,542 per person
$1,542
per person
found 1 day ago
The staff was very nice and remembered all of us by name. We loved the property as each room was a separate building. The pool was fun and the restaurant was great and had live music every night.

Reviewed on Aug 25, 2026

Peace Lodge
4.5-star property

Peace Lodge

10/10 Exceptional! (557 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to San José (SJO)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $3,112, price is now $2,119 per person
$2,119
per person
found 1 day ago
Absolutely beautiful resort. The bathroom is fabulous. The bed is comfortable and the fireplace takes a chill off in the evening. The food in the restaurants is good with lots of choices. The grounds are very well maintained. The view is awesome and the park is amazing.

Reviewed on Aug 23, 2026

The Springs Resort and Spa at Arenal
5.0-star property

The Springs Resort and Spa at Arenal

9.8/10 Exceptional! (1,008 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to San José (SJO)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Price was $2,887, price is now $2,076 per person
$2,076
per person
found 1 day ago
Great for all kinds of people! Whether you're a couple enjoying a special evening, a young family looking for a adventures, or adult families just wanting to hang out, Las Ventanas is the place to be! Our dining experience there was amazing, everything was so delicious! Can't wait to go back! Pura Vida!

Reviewed on Aug 28, 2026

Don't see what you're looking for?
See all available trips from Chicago to Central Valley
View all trips

More About Flying To Central Valley from Chicago

Route Information for Flights from Chicago to Central Valley

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SJO
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Central Valley

Orbitz gives you great deals on your flights from Chicago to Central Valley. If you also need a discount car rental or a cheap hotel room after you arrived at your destination, Orbitz has you covered.

We Offer Great Travel Deals and Discounts

When you book flights from Chicago to Central Valley with Orbitz for, you can be assured that you are getting the lowest price possible. Orbitz works constantly with our airline partners to ensure guaranteed low prices on Chicago to Central Valley flights for your trip—whether you are traveling for business or for fun with your family.

Enjoy Savings on Last-Minute Flights

If you are looking for a discount price on last-minute flights from Chicago to Central Valley, chances are that Orbitz can offer you a deal that will save you lots of money. Whether you just want to get away for the weekend or go on a vacation lasting weeks, Orbitz can help you find the best deals on Chicago to Central Valley flights that fit your budget and your itinerary for the perfect trip.

Full-Service Mobile Apps

Need more mobility when it comes to travel planning? Orbitz has easy-to-use mobile apps for iPhone, iPad, and Android, to help the traveler on the go. Not only can use the apps to find huge savings on Chicago to Central Valley flights wherever you are, but you can also check out and book discount hotel rooms too. The apps will also keep you up-to-date when it’s time to fly. Get easy access to your itinerary for flights from Chicago to Central Valley and review gate and baggage claim details too.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.