$126 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, Dec 13 - Sat, Dec 20
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$418 Roundtrip, found 4 days ago
$418
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Dec 13 from Midway Intl. to Juan Santamaría Intl., returning Sat, Dec 20, priced at $418 found 4 days ago
Sun, Dec 14 - Fri, Dec 19
RFD
Greater Rockford
SJO
Juan Santamaría Intl.
$501 Roundtrip, found 4 days ago
$501
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Dec 14 from Greater Rockford to Juan Santamaría Intl., returning Fri, Dec 19, priced at $501 found 4 days ago
Sat, Dec 13 - Sun, Dec 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$526 Roundtrip, found 7 hours ago
$526
Roundtrip
found 7 hours ago
Select avianca flight, departing Sat, Dec 13 from O'Hare Intl. to Juan Santamaría Intl., returning Sun, Dec 21, priced at $526 found 7 hours ago

Airfares from $126 One Way, $225 Round Trip from Chicago to Quepos

Prices starting at $225 for return flights and $126 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, Jan 26 - Sat, Jan 31
ORD
Chicago
SJO
San José
$225 Roundtrip, found 5 days ago
$225
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Jan 26 from Chicago to San José, returning Sat, Jan 31, priced at $225 found 5 days ago
Sat, Feb 28 - Sat, Mar 7
MDW
Chicago
SJO
San José
$286 Roundtrip, found 8 hours ago
$286
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Feb 28 from Chicago to San José, returning Sat, Mar 7, priced at $286 found 8 hours ago
Tue, Sep 15 - Fri, Sep 25
ORD
Chicago
SJO
San José
$343 Roundtrip, found 5 days ago
$343
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Sep 15 from Chicago to San José, returning Fri, Sep 25, priced at $343 found 5 days ago
Thu, Mar 19 - Mon, Mar 23
ORD
Chicago
SJO
San José
$345 Roundtrip, found 8 hours ago
$345
Roundtrip
found 8 hours ago
Select Copa flight, departing Thu, Mar 19 from Chicago to San José, returning Mon, Mar 23, priced at $345 found 8 hours ago
Sun, Jan 11 - Thu, Jan 15
ORD
Chicago
SJO
San José
$348 Roundtrip, found 10 hours ago
$348
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sun, Jan 11 from Chicago to San José, returning Thu, Jan 15, priced at $348 found 10 hours ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Apartamentos Cityzen
4.0-star property

Apartamentos Cityzen

9.6/10 Exceptional! (75 reviews)

Jan 11 - Jan 14

3 night stay

Chicago (CHI) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $952, price is now $636 per person
$636
per person
found 1 day ago
Modern, up-to-date apartmanets, great lay out, lots of light anf life, convieniently located, great dining places in the same block, one small market in the same mall area and bigger grocery store near by, fantastic service by every single staffer, Rebeca is a sweetheart, and Kellyana is on top of things. I go to CR every year once year and always go to a different place, but from now own, Apartamentos Cityzen will be my Tico-Home.

Reviewed on Mar 31, 2024

Parador Nature Resort and Spa
5.0-star property

Parador Nature Resort and Spa

9.8/10 Exceptional! (1,002 reviews)

Jan 19 - Jan 26

7 night stay

Chicago (ORD) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,109, price is now $2,409 per person
$2,409
per person
found 1 day ago
This resort was truly the best of the best!! From the moment we checked in - we were blown away and had the best vacation ever. The staff is incredibly friendly and helpful, the grounds are beautiful - so much to do and see. Our room was so spacious and comfortable. We hope to return one day…it was the best!!

Reviewed on Jun 28, 2025

Shana by the Beach Manuel Antonio
4.5-star property

Shana by the Beach Manuel Antonio

9.2/10 Wonderful! (1,001 reviews)

Jan 19 - Jan 26

7 night stay

Chicago (ORD) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,082, price is now $1,275 per person
$1,275
per person
found 1 day ago
We had a wonderful week long stay at Shana. Our 7 year old daughter had a blast at the pool and the beach nearby (hotel has direct access). We saw so much wildlife right from our balcony! Staff were very nice and helpful and assisted us with making plans in the area. Shana also set us up with transportation to/from the airport. We appreciated the hospitality!

Reviewed on Aug 7, 2025

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Quepos business class flight packages

Price found within the past 48 hours. Click for updated prices.
Parador Nature Resort and Spa
5.0-star property

Parador Nature Resort and Spa

9.8/10 Exceptional! (1,002 reviews)

Jan 7 - Jan 12

5 night stay

Chicago (ORD) to San José (SJO)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,835, price is now $2,604 per person
$2,604
per person
found 1 day ago
This resort was truly the best of the best!! From the moment we checked in - we were blown away and had the best vacation ever. The staff is incredibly friendly and helpful, the grounds are beautiful - so much to do and see. Our room was so spacious and comfortable. We hope to return one day…it was the best!!

Reviewed on Jun 28, 2025

Hotel Aguas Claras Member of the Cayuga Collection
4.5-star property

Hotel Aguas Claras Member of the Cayuga Collection

9.8/10 Exceptional! (39 reviews)

Jan 7 - Jan 12

5 night stay

Chicago (ORD) to San José (SJO)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $5,029, price is now $3,476 per person
$3,476
per person
found 1 day ago
Arenas Del Mar Beachfront & Rainforest Member of the Cayuga Collection
4.5-star property

Arenas Del Mar Beachfront & Rainforest Member of the Cayuga Collection

9.8/10 Exceptional! (314 reviews)

Jan 7 - Jan 12

5 night stay

Chicago (ORD) to San José (SJO)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $4,064, price is now $2,887 per person
$2,887
per person
found 1 day ago
Gorgeous location, and amazing service! We had a bit of an issue in the beginning, but the stall was amazing and VERY quickly helped us resolve the situation and upgraded us to the best suite in the hotel. Overall, Highly recommend!

Reviewed on Sep 23, 2019

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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.