$198 Cheap flight deals from Chicago (CHI) to Quepos (SJO)

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This Weekend's Flight Deals from Chicago to Quepos

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.

Fri, Oct 16 - Sat, Oct 24
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$545 Roundtrip, just found
$545
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 16 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Oct 24, priced at $545 just found

Airfares from $198 One Way, $419 Round Trip from Chicago to Quepos

Prices starting at $419 for return flights and $198 for one-way flights to Quepos were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 28 - Thu, Dec 10
ORD
Chicago
SJO
San José
$419 Roundtrip, found 5 days ago
$419
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Nov 28 from Chicago to San José, returning Thu, Dec 10, priced at $419 found 5 days ago
Sun, Apr 25 - Mon, May 3
ORD
Chicago
SJO
San José
$427 Roundtrip, found 3 hours ago
$427
Roundtrip
found 3 hours ago
Select Copa flight, departing Sun, Apr 25 from Chicago to San José, returning Mon, May 3, priced at $427 found 3 hours ago
Wed, Feb 3 - Sun, Feb 7
ORD
Chicago
SJO
San José
$434 Roundtrip, found 6 days ago
$434
Roundtrip
found 6 days ago
Select United flight, departing Wed, Feb 3 from Chicago to San José, returning Sun, Feb 7, priced at $434 found 6 days ago
Thu, Nov 12 - Tue, Nov 17
ORD
Chicago
SJO
San José
$439 Roundtrip, found 2 days ago
$439
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 12 from Chicago to San José, returning Tue, Nov 17, priced at $439 found 2 days ago
Sat, Oct 31 - Sat, Nov 7
ORD
Chicago
SJO
San José
$441 Roundtrip, just found
$441
Roundtrip
just found
Select United flight, departing Sat, Oct 31 from Chicago to San José, returning Sat, Nov 7, priced at $441 just found

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Peace Lodge
4.5-star property

Peace Lodge

10/10 Exceptional! (567 reviews)

Nov 14 - Nov 17

3 night stay

Chicago (CHI) to San José (SJO)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,748, price is now $1,191 per person
$1,191
per person
found 1 day ago

Noah's Forest by Tifakara
4.5-star property

Noah's Forest by Tifakara

9.8/10 Exceptional! (449 reviews)

Nov 14 - Nov 17

3 night stay

Chicago (CHI) to San José (SJO)

United • Roundtrip • Coach
Save 100% on your flight
Price was $4,129, price is now $2,650 per person
$2,650
per person
found 1 day ago

Pacuare Lodge by Böëna
4.5-star property

Pacuare Lodge by Böëna

10/10 Exceptional! (18 reviews)

Nov 12 - Nov 16

4 night stay

Chicago (CHI) to San José (SJO)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,140, price is now $2,098 per person
$2,098
per person
found 1 day ago
If you want ultimate rainforest luxury and top level service you should stay here. Not to be missed. Raft in and out via the Pacuare river and be completely enveloped by the forest and river in the middle of nowhere while having high level meals breakfast, lunch and dinner, incredible adventure programs like zip lining through the canopy and repelling down little waterfall. Seriously. 1000% The food was top tier. The service was thoughtful and personal. The staff is amazing. And they have great wifi. In the middle of nowhere. Deep jungle. The rafting is world class. I had a Linda vista villa and it was an absurd amount of space and privacy with a personal plunge pool. Come back from dinner and your lights are on, fan going and curtains drawn. Seriously, stay here. I'm coming back again someday.

Reviewed on May 27, 2026

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More About Flying To Quepos from Chicago

Route Information for Flights from Chicago to Quepos

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

Chicago to Quepos

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Frequently asked questions

Are there non-stop flights from Chicago to Quepos?
There sure is. United Airlines will fly you directly from O'Hare Intl. Airport (ORD) to Juan Santamaria Intl. Airport, so you won't have to worry about annoying layovers or missing your next flight.
What is the shortest flight from Chicago to Quepos?
With the trip from Chicago to Quepos taking a minimum of 5 hours and 39 minutes, there's plenty of time to relax and enjoy the experience. Indulge in a glass of wine and sink into your seat with an interesting book or movie.
What airlines fly from Chicago to Quepos most frequently?
If you're on the hunt for the airline with the most flights from ORD to Juan Santamaria Intl. Airport, reserve your ticket with United Airlines. This carrier has 4 flights per month along this route.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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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.