$138 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.

Fri, Aug 28 - Sun, Aug 30
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$571 Roundtrip, found 1 hour ago
$571
Roundtrip
found 1 hour ago
Select avianca flight, departing Fri, Aug 28 from O'Hare Intl. to Juan Santamaría Intl., returning Sun, Aug 30, priced at $571 found 1 hour ago

Airfares from $138 One Way, $364 Round Trip from Chicago to Alajuela

Prices starting at $364 for return flights and $138 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.

Sat, Oct 31 - Sat, Nov 7
ORD
Chicago
SJO
San José
$364 Roundtrip, found 10 hours ago
$364
Roundtrip
found 10 hours ago
Select United flight, departing Sat, Oct 31 from Chicago to San José, returning Sat, Nov 7, priced at $364 found 10 hours ago
Mon, Nov 2 - Mon, Nov 23
ORD
Chicago
SJO
San José
$366 Roundtrip, found 1 day ago
$366
Roundtrip
found 1 day ago
Select Copa flight, departing Mon, Nov 2 from Chicago to San José, returning Mon, Nov 23, priced at $366 found 1 day ago
Fri, Nov 13 - Thu, Nov 19
ORD
Chicago
SJO
San José
$378 Roundtrip, found 1 day ago
$378
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Nov 13 from Chicago to San José, returning Thu, Nov 19, priced at $378 found 1 day ago
Sat, Oct 31 - Sat, Nov 7
ORD
Chicago
SJO
San José
$378 Roundtrip, found 10 hours ago
$378
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Oct 31 from Chicago to San José, returning Sat, Nov 7, priced at $378 found 10 hours ago
Thu, Nov 12 - Thu, Nov 19
MDW
Chicago
SJO
San José
$384 Roundtrip, found 6 days ago
$384
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Nov 12 from Chicago to San José, returning Thu, Nov 19, priced at $384 found 6 days ago

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! (417 reviews)

Oct 1 - Oct 5

4 night stay

Chicago (CHI) to San José (SJO)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,344, price is now $889 per person
$889
per person
found 1 day ago
Beautiful hotel

Reviewed on Aug 20, 2026

The Springs Resort and Spa at Arenal
5.0-star property

The Springs Resort and Spa at Arenal

9.8/10 Exceptional! (1,005 reviews)

Oct 1 - Oct 5

4 night stay

Chicago (CHI) to San José (SJO)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,225, price is now $1,261 per person
$1,261
per person
found 1 day ago
Such a beautiful resort and very welcoming and accommodating staff!

Reviewed on Aug 21, 2026

Lapa Rios Lodge
4.5-star property

Lapa Rios Lodge

9.8/10 Exceptional! (28 reviews)

Oct 1 - Oct 5

4 night stay

Chicago (CHI) to San José (SJO)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,133, price is now $1,415 per person
$1,415
per person
found 1 day ago
If you want to be right in the middle of nature and wildlife this is the place to go. Most of the resort is raised up into the treetops so you can be eye level with creatures you'd usually only see way above you from the ground. The included hikes and birdwatching were wonderful with very knowledgeable and passionate guides. We also arranged a day trip to Corcovado by boat through the lodge in advance, seems pricey at first but was well worth it. Over the course of a week we saw sloths (lodge & Corcovado), monkeys (everywhere), tapirs (Corcovado), ant eaters (lodge and Corcovado), coatis (lodge), frogs and lizards (lodge) and so many different birds (everywhere). We chose a forest bungalow room which is just screened in from the outside. I was a bit worried the lack of AC might make it too hot to sleep, but at the end of April the fans in the room were enough to keep us comfortable over night. No need for alarm clocks, the howler monkeys will get you up every day. Overall a fantastic nature focused lodge that combines the ability to relax with adventure.

Reviewed on May 4, 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.