$96 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.

Sun, Feb 8 - Wed, Feb 11
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$375 Roundtrip, found 5 hours ago
$375
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Sun, Feb 8 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Feb 11, priced at $375 found 5 hours ago
Sat, Feb 7 - Mon, Feb 9
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$453 Roundtrip, found 2 days ago
$453
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Feb 7 from Midway Intl. to Juan Santamaría Intl., returning Mon, Feb 9, priced at $453 found 2 days ago

Airfares from $96 One Way, $200 Round Trip from Chicago to Quepos

Prices starting at $200 for return flights and $96 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.

Wed, Mar 4 - Tue, Mar 10
ORD
Chicago
SJO
San José
$200 Roundtrip, found 4 days ago
$200
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Mar 4 from Chicago to San José, returning Tue, Mar 10, priced at $200 found 4 days ago
Sat, Feb 28 - Sat, Mar 7
ORD
Chicago
SJO
San José
$279 Roundtrip, found 1 hour ago
$279
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Feb 28 from Chicago to San José, returning Sat, Mar 7, priced at $279 found 1 hour ago
Wed, Mar 4 - Mon, Mar 9
ORD
Chicago
SJO
San José
$303 Roundtrip, found 2 hours ago
$303
Roundtrip
found 2 hours ago
Select Copa flight, departing Wed, Mar 4 from Chicago to San José, returning Mon, Mar 9, priced at $303 found 2 hours ago
Mon, Feb 16 - Wed, Feb 18
ORD
Chicago
SJO
San José
$317 Roundtrip, found 3 days ago
$317
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Feb 16 from Chicago to San José, returning Wed, Feb 18, priced at $317 found 3 days ago
Wed, Mar 4 - Mon, Mar 9
ORD
Chicago
SJO
San José
$344 Roundtrip, found 2 hours ago
$344
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Mar 4 from Chicago to San José, returning Mon, Mar 9, priced at $344 found 2 hours ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Luxury Sky Penthouses 3-6BR Condo-Hotel at Oceano Jaco
4.0-star property

Luxury Sky Penthouses 3-6BR Condo-Hotel at Oceano Jaco

8.2/10 Very Good! (99 reviews)

Mar 7 - Mar 14

7 night stay

Chicago (CHI) to San José (SJO)

Southwest Airlines • Non-stop • Coach

San José (SJO) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
Price was $2,328, price is now $1,300 per person
$1,300
per person
found 1 day ago
love the location, the property need some up keeping.

Reviewed on Jul 11, 2019

Namu Garden Hotel & Spa - Adults Only
4.5-star property

Namu Garden Hotel & Spa - Adults Only

9.8/10 Exceptional! (230 reviews)

Mar 20 - Mar 27

7 night stay

Chicago (CHI) to San José (SJO)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,828, price is now $2,278 per person
$2,278
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

Casa Amarillo Jaco Costa Rica
3.5-star property

Casa Amarillo Jaco Costa Rica

No reviews

Mar 7 - Mar 14

7 night stay

Chicago (CHI) to San José (SJO)

Southwest Airlines • Non-stop • Coach

San José (SJO) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
Price was $3,479, price is now $2,110 per person
$2,110
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.