$109 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 24 - Tue, Jan 27
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$491 Roundtrip, found 8 hours ago
$491
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Sat, Jan 24 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jan 27, priced at $491 found 8 hours ago

Airfares from $109 One Way, $243 Round Trip from Chicago to Quepos

Prices starting at $243 for return flights and $109 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 - Wed, Feb 25
ORD
Chicago
SJO
San José
$243 Roundtrip, found 6 days ago
$243
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Feb 23 from Chicago to San José, returning Wed, Feb 25, priced at $243 found 6 days ago
Fri, Feb 27 - Fri, Mar 6
ORD
Chicago
SJO
San José
$344 Roundtrip, found 2 days ago
$344
Roundtrip
found 2 days ago
Select United flight, departing Fri, Feb 27 from Chicago to San José, returning Fri, Mar 6, priced at $344 found 2 days ago
Mon, Mar 9 - Thu, Mar 19
ORD
Chicago
SJO
San José
$374 Roundtrip, found 4 days ago
$374
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Mar 9 from Chicago to San José, returning Thu, Mar 19, priced at $374 found 4 days ago
Wed, Feb 18 - Thu, Feb 26
ORD
Chicago
SJO
San José
$385 Roundtrip, found 11 hours ago
$385
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Wed, Feb 18 from Chicago to San José, returning Thu, Feb 26, priced at $385 found 11 hours ago
Tue, Feb 3 - Sun, Feb 8
ORD
Chicago
SJO
San José
$409 Roundtrip, found 2 hours ago
$409
Roundtrip
found 2 hours ago
Select Copa flight, departing Tue, Feb 3 from Chicago to San José, returning Sun, Feb 8, priced at $409 found 2 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 22 - Feb 28

6 night stay

Chicago (CHI) to San José (SJO)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,290, price is now $750 per person
$750
per person
found 1 day ago
Adventurous location. Very nice with an amazing view. Close to rain forest park for tour.

Reviewed on Dec 29, 2024

Monte Carlo Luxury Condominiums
3.5-star property

Monte Carlo Luxury Condominiums

9.4/10 Exceptional! (94 reviews)

Feb 22 - Feb 28

6 night stay

Chicago (CHI) to San José (SJO)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,840, price is now $914 per person
$914
per person
found 1 day ago
Lovely home away from home. Nice pool and plenty of space.

Reviewed on Feb 22, 2024

Namu Garden Hotel & Spa - Adults Only
4.5-star property

Namu Garden Hotel & Spa - Adults Only

9.8/10 Exceptional! (230 reviews)

Mar 5 - Mar 8

3 night stay

Chicago (CHI) to San José (SJO)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,310, price is now $810 per person
$810
per person
found 1 day 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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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.