$138 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, Jul 4 - Fri, Jul 24
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$523 Roundtrip, found 1 hour ago
$523
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jul 4 from O'Hare Intl. to Juan Santamaría Intl., returning Fri, Jul 24, priced at $523 found 1 hour ago
Sun, Jul 5 - Fri, Jul 10
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$759 Roundtrip, found 1 hour ago
$759
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, Jul 5 from Midway Intl. to Juan Santamaría Intl., returning Fri, Jul 10, priced at $759 found 1 hour ago

Airfares from $138 One Way, $406 Round Trip from Chicago to Quepos

Prices starting at $406 for return flights and $138 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.

Thu, Aug 27 - Wed, Sep 2
ORD
Chicago
SJO
San José
$406 Roundtrip, found 1 day ago
$406
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 27 from Chicago to San José, returning Wed, Sep 2, priced at $406 found 1 day ago
Sat, Oct 17 - Fri, Oct 23
MDW
Chicago
SJO
San José
$430 Roundtrip, found 6 days ago
$430
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Oct 17 from Chicago to San José, returning Fri, Oct 23, priced at $430 found 6 days ago
Wed, Aug 5 - Thu, Aug 13
ORD
Chicago
SJO
San José
$458 Roundtrip, found 1 day ago
$458
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Chicago to San José, returning Thu, Aug 13, priced at $458 found 1 day ago
Mon, Jan 11 - Thu, Jan 21
ORD
Chicago
SJO
San José
$488 Roundtrip, found 3 days ago
$488
Roundtrip
found 3 days ago
Select United flight, departing Mon, Jan 11 from Chicago to San José, returning Thu, Jan 21, priced at $488 found 3 days ago
Sat, Aug 1 - Sun, Aug 9
ORD
Chicago
SJO
San José
$490 Roundtrip, just found
$490
Roundtrip
just found
Select Copa flight, departing Sat, Aug 1 from Chicago to San José, returning Sun, Aug 9, priced at $490 just found

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Parador Nature Resort and Spa
5.0-star property

Parador Nature Resort and Spa

9.8/10 Exceptional! (1,000 reviews)

Aug 14 - Aug 18

4 night stay

Chicago (CHI) to San José (SJO)

Copa • Non-stop roundtrip • Coach
Price was $1,487, price is now $1,037 per person
$1,037
per person
found 1 day ago
This resort was truly the best of the best!! From the moment we checked in - we were blown away and had the best vacation ever. The staff is incredibly friendly and helpful, the grounds are beautiful - so much to do and see. Our room was so spacious and comfortable. We hope to return one day…it was the best!!

Reviewed on Jun 28, 2025

Tortuga Lodge
4.5-star property

Tortuga Lodge

9.4/10 Exceptional! (266 reviews)

Aug 20 - Aug 27

7 night stay

Chicago (CHI) to San José (SJO)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $5,528, price is now $3,316 per person
$3,316
per person
found 2 hours ago
Beautiful grounds with private trail. Room has good amenities and food choices/service was excellent. It’s 10min boat ride to town so it’s a bit inconvenient (trade off is super quiet hotel) and gets costly for taxi boat ($8pp one way). There was construction above our room (#15) so we couldn’t take a nap or sleep in! Otherwise it’s a superb hotel and we would absolutely come back!

Reviewed on Oct 29, 2024

The Springs Resort and Spa at Arenal
5.0-star property

The Springs Resort and Spa at Arenal

9.8/10 Exceptional! (1,019 reviews)

Aug 6 - Aug 11

5 night stay

Chicago (CHI) to San José (SJO)

Copa • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,605, price is now $2,473 per person
$2,473
per person
found 1 hour ago
We had an amazing experience

Reviewed on May 18, 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.