$89 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 31 - Sat, Feb 7
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$450 Roundtrip, found 17 hours ago
$450
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Jan 31 from Midway Intl. to Juan Santamaría Intl., returning Sat, Feb 7, priced at $450 found 17 hours ago
Sat, Jan 31 - Sun, Feb 1
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$476 Roundtrip, just found
$476
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Jan 31 from O'Hare Intl. to Juan Santamaría Intl., returning Sun, Feb 1, priced at $476 just found
Sat, Jan 31 - Sat, Feb 7
RFD
Greater Rockford
SJO
Juan Santamaría Intl.
$544 Roundtrip, found 3 days ago
$544
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jan 31 from Greater Rockford to Juan Santamaría Intl., returning Sat, Feb 7, priced at $544 found 3 days ago

Airfares from $89 One Way, $218 Round Trip from Chicago to Quepos

Prices starting at $218 for return flights and $89 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.

Tue, Feb 24 - Wed, Mar 4
ORD
Chicago
SJO
San José
$218 Roundtrip, found 17 hours ago
$218
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Tue, Feb 24 from Chicago to San José, returning Wed, Mar 4, priced at $218 found 17 hours ago
Mon, Feb 9 - Wed, Feb 11
ORD
Chicago
SJO
San José
$301 Roundtrip, found 5 hours ago
$301
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Mon, Feb 9 from Chicago to San José, returning Wed, Feb 11, priced at $301 found 5 hours ago
Mon, Feb 9 - Tue, Feb 10
ORD
Chicago
SJO
San José
$303 Roundtrip, found 20 hours ago
$303
Roundtrip
found 20 hours ago
Select Copa flight, departing Mon, Feb 9 from Chicago to San José, returning Tue, Feb 10, priced at $303 found 20 hours ago
Mon, Feb 2 - Tue, Feb 10
ORD
Chicago
SJO
San José
$359 Roundtrip, found 4 hours ago
$359
Roundtrip
found 4 hours ago
Select United flight, departing Mon, Feb 2 from Chicago to San José, returning Tue, Feb 10, priced at $359 found 4 hours ago
Wed, Mar 4 - Mon, Mar 9
ORD
Chicago
SJO
San José
$377 Roundtrip, found 1 hour ago
$377
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Mar 4 from Chicago to San José, returning Mon, Mar 9, priced at $377 found 1 hour ago

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Umami Hotel - Adults Only
3.5-star property

Umami Hotel - Adults Only

9.4/10 Exceptional! (461 reviews)

Mar 11 - Mar 18

7 night stay

Chicago (CHI) to San José (SJO)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,591, price is now $868 per person
$868
per person
found 1 day ago
Boutique hotel that is central to everything. The spa is not a full service spa as you would expect however, the services received were great.

Reviewed on Mar 31, 2025

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

Namu Garden Hotel & Spa - Adults Only

9.8/10 Exceptional! (230 reviews)

Mar 11 - Mar 18

7 night stay

Chicago (CHI) to San José (SJO)

United • Roundtrip • Coach
Price was $3,164, price is now $1,539 per person
$1,539
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

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)

Mar 9 - Mar 14

5 night stay

Chicago (CHI) to San José (SJO)

United • Roundtrip • Coach
Price was $5,832, price is now $3,047 per person
$3,047
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

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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

Whether you want to book cheap flights from Chicago to Quepos or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Chicago to Quepos flights.

Make the Most of Your Vacation

Not only does Orbitz have cheap deals for Chicago to Quepos flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Quepos.

Planning on the Go

Book your flights from Chicago to Quepos wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Chicago to Quepos flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.

Craft Your Perfect Vacation

Orbitz takes the stress out of vacation planning with great deals on flights from Chicago to Quepos, hotels, car rentals, cruises, and more. Mix and match results for your perfect trip, or book a complete vacation package.

Keep Informed With Orbitz

With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Chicago to Quepos flights. The alerts can be sent straight to your mobile phone or email.

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.