$136 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, Jun 20 - Wed, Jun 24
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$621 Roundtrip, found 5 days ago
$621
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Jun 20 from Midway Intl. to Juan Santamaría Intl., returning Wed, Jun 24, priced at $621 found 5 days ago
Sat, Jun 20 - Sat, Jun 27
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$718 Roundtrip, found 3 hours ago
$718
Roundtrip
found 3 hours ago
Select avianca flight, departing Sat, Jun 20 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 27, priced at $718 found 3 hours ago

Airfares from $136 One Way, $368 Round Trip from Chicago to Quepos

Prices starting at $368 for return flights and $136 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.

Sat, Aug 22 - Sun, Sep 6
MDW
Chicago
SJO
San José
$368 Roundtrip, found 1 day ago
$368
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Aug 22 from Chicago to San José, returning Sun, Sep 6, priced at $368 found 1 day ago
Wed, Aug 26 - Tue, Sep 1
ORD
Chicago
SJO
San José
$392 Roundtrip, found 5 days ago
$392
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Aug 26 from Chicago to San José, returning Tue, Sep 1, priced at $392 found 5 days ago
Sat, Jul 25 - Sun, Aug 2
ORD
Chicago
SJO
San José
$478 Roundtrip, just found
$478
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jul 25 from Chicago to San José, returning Sun, Aug 2, priced at $478 just found
Sat, Nov 14 - Sat, Nov 21
ORD
Chicago
SJO
San José
$488 Roundtrip, found 2 days ago
$488
Roundtrip
found 2 days ago
Select United flight, departing Sat, Nov 14 from Chicago to San José, returning Sat, Nov 21, priced at $488 found 2 days ago
Sat, Jul 25 - Sat, Aug 1
ORD
Chicago
SJO
San José
$490 Roundtrip, found 3 hours ago
$490
Roundtrip
found 3 hours ago
Select Copa flight, departing Sat, Jul 25 from Chicago to San José, returning Sat, Aug 1, priced at $490 found 3 hours ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Dar Lamia Boutique Hotel
3.5-star property

Dar Lamia Boutique Hotel

8/10 Very Good! (27 reviews)

Jul 16 - Jul 21

5 night stay

Chicago (ORD) to San José (SJO)

Avianca • Non-stop roundtrip • Coach
Price was $1,382, price is now $920 per person
$920
per person
found 3 hours ago
The staff was so kind. They welcomed us with personal touches!

Reviewed on Feb 27, 2026

Casa Lamia
3.5-star property

Casa Lamia

8.4/10 Very Good! (104 reviews)

Jul 25 - Aug 2

8 night stay

Chicago (CHI) to San José (SJO)

Copa • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,920, price is now $1,088 per person
$1,088
per person
just found
Si Como No Resort, Spa and Wildlife Refuge
3.5-star property

Si Como No Resort, Spa and Wildlife Refuge

9.4/10 Exceptional! (796 reviews)

Jul 25 - Aug 2

8 night stay

Chicago (CHI) to San José (SJO)

Copa • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,691, price is now $1,670 per person
$1,670
per person
just found
Great property close to Manuel Antonio park! Rooms are spread across and will require lot of walking. Overall great stay and will repeat if I am in the area.

Reviewed on Apr 17, 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.