$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.

Sun, Mar 8 - Thu, Mar 12
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$384 Roundtrip, found 2 days ago
$384
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Mar 8 from O'Hare Intl. to Juan Santamaría Intl., returning Thu, Mar 12, priced at $384 found 2 days ago
Fri, Mar 6 - Sat, Mar 14
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$422 Roundtrip, found 5 days ago
$422
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Mar 6 from Midway Intl. to Juan Santamaría Intl., returning Sat, Mar 14, priced at $422 found 5 days ago

Airfares from $133 One Way, $314 Round Trip from Chicago to Quepos

Prices starting at $314 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.

Tue, Mar 17 - Wed, Mar 18
ORD
Chicago
SJO
San José
$314 Roundtrip, found 2 days ago
$314
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Mar 17 from Chicago to San José, returning Wed, Mar 18, priced at $314 found 2 days ago
Sat, May 30 - Thu, Jun 4
ORD
Chicago
SJO
San José
$350 Roundtrip, found 2 days ago
$350
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 30 from Chicago to San José, returning Thu, Jun 4, priced at $350 found 2 days ago
Mon, May 4 - Sat, May 9
RFD
Rockford
SJO
San José
$354 Roundtrip, found 7 hours ago
$354
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, May 4 from Rockford to San José, returning Sat, May 9, priced at $354 found 7 hours ago
Mon, May 4 - Tue, May 12
ORD
Chicago
SJO
San José
$361 Roundtrip, found 1 day ago
$361
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, May 4 from Chicago to San José, returning Tue, May 12, priced at $361 found 1 day ago
Mon, May 4 - Sat, May 9
MDW
Chicago
SJO
San José
$403 Roundtrip, found 7 hours ago
$403
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Mon, May 4 from Chicago to San José, returning Sat, May 9, priced at $403 found 7 hours 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 23 - Apr 28

5 night stay

Chicago (CHI) to San José (SJO)

Copa • Non-stop roundtrip • Coach
Price was $998, price is now $609 per person
$609
per person
found 3 hours 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 18 - Apr 25

7 night stay

Chicago (CHI) to San José (SJO)

United • Roundtrip • Coach
Save 100% on your flight
Price was $4,983, price is now $2,594 per person
$2,594
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

Lia Hotel Jaco
3.5-star property

Lia Hotel Jaco

9.4/10 Exceptional! (69 reviews)

Apr 9 - Apr 13

4 night stay

Chicago (CHI) to San José (SJO)

Copa • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,517, price is now $933 per person
$933
per person
found 1 day ago
Beautiful, clean hotel with amazing staff right on the beach, quiet, secluded, but still centrally located. Had a great time. I recommend.

Reviewed on Nov 14, 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

Great Deals on Flights From Chicago to Quepos

Spend more of your time and money at Quepos instead of sitting at your computer, searching for discount Chicago to Quepos flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to Quepos.

Flights That Fit Your Budget

Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to Quepos flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.

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Search for Flights from Chicago to Quepos on the Go

Orbitz offers free mobile apps for iPad, iPhone, and Android-based devices, so even the busiest trip-planner can research and book flights from Chicago to Quepos. Find cheap Chicago to Quepos flights, research local festivities and attractions, and book reservations while sitting in the salon. Orbitz will also update you on flight delays with free alerts sent to your mobile phone or email address, so you’re never left in the dark.

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.