$215 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, Oct 31 - Wed, Nov 4
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$632 Roundtrip, found 2 days ago
$632
Roundtrip
found 2 days ago
Select avianca flight, departing Sat, Oct 31 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Nov 4, priced at $632 found 2 days ago

Airfares from $215 One Way, $424 Round Trip from Chicago to Quepos

Prices starting at $424 for return flights and $215 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.

Sun, Jan 24 - Wed, Jan 27
ORD
Chicago
SJO
San José
$424 Roundtrip, found 2 days ago
$424
Roundtrip
found 2 days ago
Select United flight, departing Sun, Jan 24 from Chicago to San José, returning Wed, Jan 27, priced at $424 found 2 days ago
Fri, Jan 22 - Tue, Jan 26
ORD
Chicago
SJO
San José
$427 Roundtrip, found 4 hours ago
$427
Roundtrip
found 4 hours ago
Select Copa flight, departing Fri, Jan 22 from Chicago to San José, returning Tue, Jan 26, priced at $427 found 4 hours ago
Fri, Jan 22 - Tue, Jan 26
ORD
Chicago
SJO
San José
$439 Roundtrip, found 4 hours ago
$439
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Jan 22 from Chicago to San José, returning Tue, Jan 26, priced at $439 found 4 hours ago
Mon, Jan 25 - Thu, Feb 11
MDW
Chicago
SJO
San José
$440 Roundtrip, found 3 days ago
$440
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Jan 25 from Chicago to San José, returning Thu, Feb 11, priced at $440 found 3 days ago
Tue, Feb 16 - Sun, Feb 28
ORD
Chicago
SJO
San José
$472 Roundtrip, just found
$472
Roundtrip
just found
Select avianca flight, departing Tue, Feb 16 from Chicago to San José, returning Sun, Feb 28, priced at $472 just found

Quepos economy flight packages

Price found within the past 48 hours. Click for updated prices.
Noah's Forest by Tifakara
4.5-star property

Noah's Forest by Tifakara

9.8/10 Exceptional! (461 reviews)

Dec 4 - Dec 8

4 night stay

Chicago (CHI) to San José (SJO)

JetBlue Airways • Non-stop • Coach

San José (SJO) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,569, price is now $1,666 per person
$1,666
per person
found 1 day ago

Gaia Collection Hotels - Adults only
4.0-star property

Gaia Collection Hotels - Adults only

9.8/10 Exceptional! (10 reviews)

Dec 3 - Dec 10

7 night stay

Chicago (CHI) to San José (SJO)

American Airlines • Non-stop roundtrip • Coach
Price was $5,647, price is now $2,952 per person
$2,952
per person
found 1 day ago
Our stay at Gaia Hotel & Reserve was wonderful, but what truly made it exceptional was the outstanding level of service. From the moment we arrived, we were incredibly impressed by the warmth, professionalism, and genuine attentiveness of the entire staff. You can tell that providing exceptional service is part of the culture of this hotel. Everyone made us feel welcomed, cared for, and completely at ease throughout our stay. A few people especially stood out: Chris at the front desk and concierge was fantastic—always attentive, knowledgeable, and ready to help. Oscar was wonderful from the moment we arrived, helping with our luggage and transporting us around the property with such kindness and a great attitude. The restaurant staff was equally impressive, especially Abraham and Jack, along with the rest of the team, who were consistently warm, helpful, and attentive. The property itself is beautiful, but for us, the people were the true highlight. Exceptional hospitality and a level of service that we will absolutely remember. Thank you to the entire Gaia team for making our stay in Manuel Antonio so special!

Reviewed on Aug 17, 2026

The Springs Resort and Spa at Arenal
5.0-star property

The Springs Resort and Spa at Arenal

9.8/10 Exceptional! (1,000 reviews)

Dec 4 - Dec 8

4 night stay

Chicago (CHI) to San José (SJO)

JetBlue Airways • Non-stop • Coach

San José (SJO) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,045, price is now $1,705 per person
$1,705
per person
found 1 day ago

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Quepos business class flight packages

Price found within the past 48 hours. Click for updated prices.
Xandari Resort And Spa
4.0-star property

Xandari Resort And Spa

9.6/10 Exceptional! (1,003 reviews)

Dec 5 - Dec 12

7 night stay

Chicago (ORD) to San José (SJO)

American Airlines • Roundtrip • BusinessClass
Price was $3,813, price is now $2,863 per person
$2,863
per person
found 1 day ago

ETM Wellness Private Retreat
3.5-star property

ETM Wellness Private Retreat

10/10 Exceptional! (1 review)

Dec 5 - Dec 12

7 night stay

Chicago (ORD) to San José (SJO)

American Airlines • Roundtrip • BusinessClass
Price was $4,199, price is now $3,088 per person
$3,088
per person
found 1 day ago
I took the family for a stay at the ETM Private Wellness Retreat in Costa Rica. The villa is more beautiful than the pictures shows very spacious. The owner and the staff were attentive and freindly, local restaurant, market and shops minutes away. You think the pool is the main attraction, think again. Overall ETM Private Wellness Retreat is a place a plan on going back.

Reviewed on Aug 25, 2026

Finca Rosa Blanca Coffee Farm and Inn
4.0-star property

Finca Rosa Blanca Coffee Farm and Inn

9.6/10 Exceptional! (283 reviews)

Dec 5 - Dec 12

7 night stay

Chicago (ORD) to San José (SJO)

American Airlines • Roundtrip • BusinessClass
Price was $3,835, price is now $3,161 per person
$3,161
per person
found 1 day ago
Eco friendly property in a beautiful, lush, and tranquil environment. The staff was exceptional in making me feel welcomed, and ensuring that all of my needs and expectations were met. The meals were delicious and I even had the pleasure of meeting the owner who took time out of his day to have coffee with me and tell me the history of the property. They made me feel like I was a part of the family. I also enjoyed bird watching and the coffee farm tour. A great place to unplug and reconnect with nature. Exceptional!

Reviewed on Oct 27, 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

If you feel you cannot afford the costs involved to your dream trip to a local or international destination happen, think again! Orbitz gives you incredible deals on flights from Chicago to Quepos. Now you can book guaranteed low fares for Chicago to Quepos flights and plan your trip with confidence.

Great deals on flights from Chicago to Quepos

Cheap airfares on Chicago to Quepos flights allow you to stick to your budget and still have a great trip. We give you guaranteed low prices and make it easy to research and book discount flights using our website. Additionally, you can add your frequent flyer numbers to your Orbitz account profile, and this information will automatically be included on all your future reservations for qualified flights from Chicago to Quepos.

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Chicago to Quepos flights at discounted rates

Finding flights at the right prices can be difficult if you are not sure where to look. Don’t ruin your trip by spending more on your flights than your budget allows. Orbitz gives you guaranteed low fares on Chicago to Quepos flights and amazing discount offers on car rentals, hotels, and even fun activities in your destination. Your dream trip is more affordable than ever with Orbitz.

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.