$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, Aug 29 - Mon, Aug 31
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$570 Roundtrip, found 4 hours ago
$570
Roundtrip
found 4 hours ago
Select avianca flight, departing Sat, Aug 29 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Aug 31, priced at $570 found 4 hours ago

Airfares from $138 One Way, $364 Round Trip from Chicago to Quepos

Prices starting at $364 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.

Sun, Jan 24 - Fri, Jan 29
ORD
Chicago
SJO
San José
$364 Roundtrip, found 1 hour ago
$364
Roundtrip
found 1 hour ago
Select United flight, departing Sun, Jan 24 from Chicago to San José, returning Fri, Jan 29, priced at $364 found 1 hour ago
Mon, Nov 9 - Mon, Nov 16
ORD
Chicago
SJO
San José
$366 Roundtrip, found 1 day ago
$366
Roundtrip
found 1 day ago
Select Copa flight, departing Mon, Nov 9 from Chicago to San José, returning Mon, Nov 16, priced at $366 found 1 day ago
Fri, Nov 13 - Thu, Nov 19
ORD
Chicago
SJO
San José
$378 Roundtrip, found 3 days ago
$378
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Nov 13 from Chicago to San José, returning Thu, Nov 19, priced at $378 found 3 days ago
Sun, Oct 4 - Sat, Oct 10
ORD
Chicago
SJO
San José
$378 Roundtrip, found 1 hour ago
$378
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, Oct 4 from Chicago to San José, returning Sat, Oct 10, priced at $378 found 1 hour ago
Fri, Oct 23 - Mon, Oct 26
MDW
Chicago
SJO
San José
$393 Roundtrip, found 4 hours ago
$393
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Oct 23 from Chicago to San José, returning Mon, Oct 26, priced at $393 found 4 hours ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Vista Suites at Parador
2.5-star property

Vista Suites at Parador

9.6/10 Exceptional! (10 reviews)

Oct 2 - Oct 6

4 night stay

Chicago (CHI) to San José (SJO)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,394, price is now $1,412 per person
$1,412
per person
found 1 day ago
Site magnifique - nous avons tout aimé, seul désavantage -impossible d’accéder à des restos ou activités extérieurs à l’hôtel sans voiture.

Reviewed on Apr 2, 2026

Tortuga Lodge
4.5-star property

Tortuga Lodge

9.4/10 Exceptional! (268 reviews)

Oct 3 - Oct 10

7 night stay

Chicago (ORD) to San José (SJO)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,680, price is now $2,753 per person
$2,753
per person
found 11 hours ago
.

Reviewed on Aug 17, 2026

Pacuare Lodge by Böëna
4.5-star property

Pacuare Lodge by Böëna

10/10 Exceptional! (18 reviews)

Oct 5 - Oct 9

4 night stay

Chicago (CHI) to San José (SJO)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,599, price is now $1,664 per person
$1,664
per person
found 1 day ago
If you want ultimate rainforest luxury and top level service you should stay here. Not to be missed. Raft in and out via the Pacuare river and be completely enveloped by the forest and river in the middle of nowhere while having high level meals breakfast, lunch and dinner, incredible adventure programs like zip lining through the canopy and repelling down little waterfall. Seriously. 1000% The food was top tier. The service was thoughtful and personal. The staff is amazing. And they have great wifi. In the middle of nowhere. Deep jungle. The rafting is world class. I had a Linda vista villa and it was an absurd amount of space and privacy with a personal plunge pool. Come back from dinner and your lights are on, fan going and curtains drawn. Seriously, stay here. I'm coming back again someday.

Reviewed on May 27, 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.