$133 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, Feb 20 - Mon, Feb 23
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$528 Roundtrip, just found
$528
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Feb 20 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Feb 23, priced at $528 just found

Airfares from $133 One Way, $282 Round Trip from Chicago to Quepos

Prices starting at $282 for return flights and $133 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.

Mon, Mar 2 - Tue, Mar 10
ORD
Chicago
SJO
San José
$282 Roundtrip, found 7 hours ago
$282
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Mon, Mar 2 from Chicago to San José, returning Tue, Mar 10, priced at $282 found 7 hours ago
Sat, Feb 21 - Sat, Mar 7
ORD
Chicago
SJO
San José
$327 Roundtrip, found 3 days ago
$327
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Chicago to San José, returning Sat, Mar 7, priced at $327 found 3 days ago
Wed, Apr 22 - Wed, Apr 29
ORD
Chicago
SJO
San José
$336 Roundtrip, found 1 hour ago
$336
Roundtrip
found 1 hour ago
Select Copa flight, departing Wed, Apr 22 from Chicago to San José, returning Wed, Apr 29, priced at $336 found 1 hour ago
Wed, Apr 22 - Wed, Apr 29
ORD
Chicago
SJO
San José
$358 Roundtrip, found 1 hour ago
$358
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Apr 22 from Chicago to San José, returning Wed, Apr 29, priced at $358 found 1 hour ago
Fri, Mar 6 - Sat, Mar 14
MDW
Chicago
SJO
San José
$376 Roundtrip, found 4 days ago
$376
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Mar 6 from Chicago to San José, returning Sat, Mar 14, priced at $376 found 4 days ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ronny's Flat Manuel Antonio
3.0-star property

Ronny's Flat Manuel Antonio

9.8/10 Exceptional! (6 reviews)

Apr 4 - Apr 11

7 night stay

Chicago (ORD) to San José (SJO)

Air Canada • Non-stop • Coach

San José (SJO) to Chicago (ORD)

Volaris Costa Rica • Non-stop • Coach
Price was $1,391, price is now $864 per person
$864
per person
found 1 day ago
The Springs Resort and Spa at Arenal
5.0-star property

The Springs Resort and Spa at Arenal

9.8/10 Exceptional! (1,002 reviews)

Apr 11 - Apr 18

7 night stay

Chicago (ORD) to San José (SJO)

Spirit Airlines • Non-stop • Coach

San José (SJO) to Chicago (ORD)

American Airlines • Non-stop • Coach
Price was $4,685, price is now $2,255 per person
$2,255
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

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

Namu Garden Hotel & Spa - Adults Only

9.8/10 Exceptional! (230 reviews)

Mar 23 - Mar 30

7 night stay

Chicago (CHI) to San José (SJO)

United • Coach

San José (SJO) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $2,803, price is now $1,710 per person
$1,710
per person
found 12 hours 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

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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

Orbitz is the best place to find guaranteed low prices on Chicago to Quepos flights. Because of our cutting-edge mobile tools and low fares on domestic and international flights, Orbitz is the best starting point for travelers.

Find Cheap Chicago to Quepos Flights

Orbitz offers free mobile apps for iPhone and Android devices—a great way to find fantastic deals on flights from Chicago to Quepos. Not only that, but you can check the status of your flight or even book low cost hotel rooms with the apps or on m.orbitz.com.

Get Miles and Points for Your Flight

Simply enter your frequent flyer information while booking to get miles or points for qualifying Chicago to Quepos flights. This information can all be saved in your Orbitz account, which means it will not have to be entered each time you take advantage of a great air fare deal.

Flight Alerts Take Away the Stress

Orbitz does not want travelers to worry on their flights from Chicago to Quepos. We keep you updated on any flight changes for Chicago to Quepos flights with alerts sent directly to your email or a mobile device. These alerts can also be sent to friends and family.

Discount Travel Planning Made Simple

You will have no problems finding budget flights from Chicago to Quepos on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.

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.