$106 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, Jan 17 - Wed, Jan 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$401 Roundtrip, found 8 hours ago
$401
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Sat, Jan 17 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 21, priced at $401 found 8 hours ago
Sat, Jan 17 - Fri, Jan 23
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$489 Roundtrip, found 11 hours ago
$489
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Jan 17 from Midway Intl. to Juan Santamaría Intl., returning Fri, Jan 23, priced at $489 found 11 hours ago
Fri, Jan 16 - Sat, Jan 24
RFD
Greater Rockford
SJO
Juan Santamaría Intl.
$539 Roundtrip, found 3 days ago
$539
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Jan 16 from Greater Rockford to Juan Santamaría Intl., returning Sat, Jan 24, priced at $539 found 3 days ago

Airfares from $106 One Way, $232 Round Trip from Chicago to Quepos

Prices starting at $232 for return flights and $106 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, Feb 23 - Thu, Feb 26
ORD
Chicago
SJO
San José
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Feb 23 from Chicago to San José, returning Thu, Feb 26, priced at $232 found 1 day ago
Mon, Apr 6 - Fri, Apr 10
MDW
Chicago
SJO
San José
$315 Roundtrip, found 11 hours ago
$315
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Apr 6 from Chicago to San José, returning Fri, Apr 10, priced at $315 found 11 hours ago
Sat, Jan 31 - Sat, Feb 7
ORD
Chicago
SJO
San José
$347 Roundtrip, found 9 hours ago
$347
Roundtrip
found 9 hours ago
Select Copa flight, departing Sat, Jan 31 from Chicago to San José, returning Sat, Feb 7, priced at $347 found 9 hours ago
Fri, Jan 30 - Tue, Feb 3
RFD
Rockford
SJO
San José
$359 Roundtrip, found 3 days ago
$359
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Jan 30 from Rockford to San José, returning Tue, Feb 3, priced at $359 found 3 days ago
Wed, Jan 28 - Sat, Jan 31
ORD
Chicago
SJO
San José
$376 Roundtrip, found 15 hours ago
$376
Roundtrip
found 15 hours ago
Select avianca flight, departing Wed, Jan 28 from Chicago to San José, returning Sat, Jan 31, priced at $376 found 15 hours ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Arenal Roca Suites
3.0-star property

Arenal Roca Suites

8.4/10 Very Good! (40 reviews)

Feb 18 - Feb 25

7 night stay

Chicago (CHI) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,233, price is now $591 per person
$591
per person
found 20 hours ago
Adventurous location. Very nice with an amazing view. Close to rain forest park for tour.

Reviewed on Dec 29, 2024

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)

Feb 25 - Mar 2

5 night stay

Chicago (CHI) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $4,031, price is now $1,899 per person
$1,899
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)

Feb 21 - Feb 28

7 night stay

Chicago (ORD) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $3,147, price is now $1,562 per person
$1,562
per person
found 9 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

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Orbitz is your number one source for low fares for Chicago to Quepos flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Quepos. Need hotels too? You can book them last minute on your mobile phone.

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.