$78 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.

Sat, Sep 20 - Mon, Sep 22
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$557 Roundtrip, found 9 hours ago
$557
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Sep 22, priced at $557 found 9 hours ago

Airfares from $78 One Way, $185 Round Trip from Chicago to Quepos

Prices starting at $185 for return flights and $78 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.

Tue, Sep 30 - Thu, Oct 2
ORD
Chicago
SJO
San José
$185 Roundtrip, just found
$185
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Sep 30 from Chicago to San José, returning Thu, Oct 2, priced at $185 just found
Thu, Oct 23 - Sun, Oct 26
ORD
Chicago
SJO
San José
$328 Roundtrip, just found
$328
Roundtrip
just found
Select Copa flight, departing Thu, Oct 23 from Chicago to San José, returning Sun, Oct 26, priced at $328 just found
Tue, Nov 11 - Sat, Nov 15
ORD
Chicago
SJO
San José
$329 Roundtrip, just found
$329
Roundtrip
just found
Select American Airlines flight, departing Tue, Nov 11 from Chicago to San José, returning Sat, Nov 15, priced at $329 just found
Thu, Oct 2 - Wed, Oct 15
ORD
Chicago
SJO
San José
$340 Roundtrip, found 4 days ago
$340
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Oct 2 from Chicago to San José, returning Wed, Oct 15, priced at $340 found 4 days ago
Mon, Nov 10 - Wed, Nov 19
MDW
Chicago
SJO
San José
$342 Roundtrip, found 6 days ago
$342
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Nov 10 from Chicago to San José, returning Wed, Nov 19, priced at $342 found 6 days ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Namu Garden Hotel & Spa - Adults Only
4.5-star property

Namu Garden Hotel & Spa - Adults Only

9.8/10 Exceptional! (214 reviews)

Nov 1 - Nov 8

7 night stay

Chicago (CHI) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $2,830, price is now $1,232 per person
$1,232
per person
found 1 day ago
Amazing stay at Namu. Beautiful architecture and décor and everything kept very clean. Wonderful staff and very tranquil. Perfect location tucked away from the hustle and bustle but still just a few minutes walk to the shops and water.

Reviewed on Jun 6, 2025

Vista Suites at Parador
2.5-star property

Vista Suites at Parador

No reviews

Nov 1 - Nov 8

7 night stay

Chicago (CHI) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $3,597, price is now $1,538 per person
$1,538
per person
found 1 day ago
Origins Lodge
4.0-star property

Origins Lodge

8.8/10 Excellent! (3 reviews)

Nov 8 - Nov 15

7 night stay

Chicago (CHI) to San José (SJO)

American Airlines • Roundtrip • Coach
Price was $5,711, price is now $2,731 per person
$2,731
per person
found 1 day ago
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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

It has never been easier to find cheap Chicago to Quepos flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.

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Get the Best Deals on Chicago to Quepos Flights

Finding great deals on flights from Chicago to Quepos is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Quepos vacation even more.

Pile Up Miles With Discount Air Tickets

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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.

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.