$215 Cheap flight deals from Chicago (CHI) to Alajuela (SJO)

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This Weekend's Flight Deals from Chicago to Alajuela

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 1 day ago
$632
Roundtrip
found 1 day ago
Select avianca flight, departing Sat, Oct 31 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Nov 4, priced at $632 found 1 day ago

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

Prices starting at $424 for return flights and $215 for one-way flights to Alajuela 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 23 hours ago
$427
Roundtrip
found 23 hours ago
Select Copa flight, departing Fri, Jan 22 from Chicago to San José, returning Tue, Jan 26, priced at $427 found 23 hours ago
Sat, Jan 23 - Sat, Jan 30
ORD
Chicago
SJO
San José
$439 Roundtrip, found 1 hour ago
$439
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Jan 23 from Chicago to San José, returning Sat, Jan 30, priced at $439 found 1 hour 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
Mon, Feb 1 - Tue, Feb 9
ORD
Chicago
SJO
San José
$472 Roundtrip, just found
$472
Roundtrip
just found
Select avianca flight, departing Mon, Feb 1 from Chicago to San José, returning Tue, Feb 9, priced at $472 just found

Alajuela 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 8 - Dec 13

5 night stay

Chicago (CHI) to San José (SJO)

United • Non-stop roundtrip • Coach
Price was $2,318, price is now $1,547 per person
$1,547
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 21 hours 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

Peace Lodge
4.5-star property

Peace Lodge

10/10 Exceptional! (570 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 $2,466, price is now $1,633 per person
$1,633
per person
found 22 hours ago
Clean rooms the whole property was clean, food was good, front desk and waiter staff was exceptional, kid friendly and everything was easily accessible

Reviewed on Oct 27, 2026

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Alajuela 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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Alajuela first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Playa Bejuco
3.0-star property

Hotel Playa Bejuco

8.8/10 Excellent! (328 reviews)

Dec 15 - Dec 22

7 night stay

Chicago (ORD) to San José (SJO)

United • Non-stop roundtrip • FirstClass
Price was $2,025, price is now $1,580 per person
$1,580
per person
found 1 day ago

Alma Del Pacifico Beach Hotel & Spa
4.0-star property

Alma Del Pacifico Beach Hotel & Spa

9.6/10 Exceptional! (361 reviews)

Dec 15 - Dec 22

7 night stay

Chicago (ORD) to San José (SJO)

United • Non-stop roundtrip • FirstClass
Price was $3,410, price is now $2,641 per person
$2,641
per person
found 1 day ago
Hotel Boutique con habitaciones amplias y cómodas, buen desayuno, justo frente a la playa y con un área de piscinas muy cómoda apenas para unos días de relajación.

Reviewed on Oct 28, 2026

Clandestino Beach
3.0-star property

Clandestino Beach

9/10 Wonderful! (609 reviews)

Dec 15 - Dec 22

7 night stay

Chicago (ORD) to San José (SJO)

United • Non-stop roundtrip • FirstClass
Price was $2,448, price is now $1,993 per person
$1,993
per person
found 1 day ago
If you don’t mind a nasty raccoon in your room. In our closet. After alerting staff- took them two hours to rid it. The guy came in and left saying he’d be back to get it out. Meanwhile 2 hours later- I walk into the closed restaurant. He was there just sitting at the bar with no one around watching movies on his laptop. Our first night getting to the place and we were ready to go to bed. Two hours later- he came back! Single ladies. No one told us there would be absolutely NO customer service. The next day woke to a flat tire which happened on the property. No food available. No drinks upon arrival. Not prepared for guests. Someone dropped the ball Think they let staff off bot releasing we booked months ago. A very isolated place -use caution with driving at night. We went out on a tour. Made sure to make it back by dark- thinking we would grab a bite there as the roads a not lit and tons of pot holes. Only to be told - they had a group of 30 check out prior to our arrival and they weren’t prepared for us. Mind you- only the three of us ladies were the ONLY guests there. Offered no drink’s Told us no cook on site. We decided ok- we ate lunch out - Let’s just relax in the pool and get up with the sun and find breaksfast. The raccoon shows up again. Apparently it’ comes with this resort. Poops in the pool. Decided against getting sick so we exited pool asap. That’s after we see raccoon coming out of the kitchen at the open air restaurant. No Go!!!

Reviewed on Oct 26, 2026

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More About Flying To Alajuela from Chicago

Route Information for Flights from Chicago to Alajuela

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SJO
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Alajuela

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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.