$139 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, Mar 20 - Fri, Apr 3
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$692 Roundtrip, found 2 hours ago
$692
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Fri, Mar 20 from O'Hare Intl. to Juan Santamaría Intl., returning Fri, Apr 3, priced at $692 found 2 hours ago
Fri, Mar 20 - Thu, Mar 26
RFD
Greater Rockford
SJO
Juan Santamaría Intl.
$854 Roundtrip, found 4 days ago
$854
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Mar 20 from Greater Rockford to Juan Santamaría Intl., returning Thu, Mar 26, priced at $854 found 4 days ago
Sun, Mar 22 - Sun, Mar 29
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$876 Roundtrip, found 4 days ago
$876
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, Mar 22 from Midway Intl. to Juan Santamaría Intl., returning Sun, Mar 29, priced at $876 found 4 days ago

Airfares from $139 One Way, $352 Round Trip from Chicago to Quepos

Prices starting at $352 for return flights and $139 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 20 - Thu, Aug 27
ORD
Chicago
SJO
San José
$352 Roundtrip, found 5 days ago
$352
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Aug 20 from Chicago to San José, returning Thu, Aug 27, priced at $352 found 5 days ago
Thu, May 14 - Tue, May 19
RFD
Rockford
SJO
San José
$384 Roundtrip, found 1 day ago
$384
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, May 14 from Rockford to San José, returning Tue, May 19, priced at $384 found 1 day ago
Mon, May 11 - Fri, May 15
ORD
Chicago
SJO
San José
$415 Roundtrip, found 17 hours ago
$415
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Mon, May 11 from Chicago to San José, returning Fri, May 15, priced at $415 found 17 hours ago
Fri, Dec 4 - Thu, Dec 10
ORD
Chicago
SJO
San José
$462 Roundtrip, found 6 days ago
$462
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Dec 4 from Chicago to San José, returning Thu, Dec 10, priced at $462 found 6 days ago
Fri, Apr 17 - Fri, Apr 24
ORD
Chicago
SJO
San José
$470 Roundtrip, found 2 hours ago
$470
Roundtrip
found 2 hours ago
Select Copa flight, departing Fri, Apr 17 from Chicago to San José, returning Fri, Apr 24, priced at $470 found 2 hours ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Volcano Lodge Hotel & Thermal Experience
4.0-star property

Volcano Lodge Hotel & Thermal Experience

9.4/10 Exceptional! (1,005 reviews)

Apr 17 - Apr 23

6 night stay

Chicago (CHI) to San José (SJO)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,760, price is now $1,119 per person
$1,119
per person
found 1 day ago
Private hot springs pool

Reviewed on Oct 22, 2024

The Springs Resort and Spa at Arenal
5.0-star property

The Springs Resort and Spa at Arenal

9.8/10 Exceptional! (1,009 reviews)

May 3 - May 10

7 night stay

Chicago (CHI) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,212, price is now $2,527 per person
$2,527
per person
found 1 day ago
Beautiful property! Large rooms, wonderful staff and lots to do. The pools were great and club rio rafting was a blast. Highly recommend!

Reviewed on Jun 22, 2025

Ocean View Penthouses by Issimo - Adults Only
3.5-star property

Ocean View Penthouses by Issimo - Adults Only

9/10 Wonderful! (11 reviews)

May 8 - May 12

4 night stay

Chicago (ORD) to San José (SJO)

Spirit Airlines • Non-stop • Coach

San José (SJO) to Chicago (ORD)

Southwest Airlines • Non-stop • Coach
Price was $1,922, price is now $1,175 per person
$1,175
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

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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.

More Destinations

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.