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THE BUOY

Santurce

€492

per person

20 Jan - 26 Jan

found 1 day ago

Return direct flight included

Chicago (ORD) to San Juan (SJU)

10/10 Exceptional! (27 reviews)

Very clean adorable had everything I needed!!!

Reviewed on 11 Nov 2025

Ola Boutique Hotel

Condado

€732

per person

20 Jan - 26 Jan

found 1 day ago

Return direct flight included

Chicago (ORD) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

This is a great budget hotel close to everything. The lobby is super cute, the staff was incredibly friendly and nice—and overall I would recommend. However, our room was in need of repairs and based on what I saw of the other rooms, I felt that we got the poorest room on the floor so I wasn’t happy about that but it wasn’t a dealbreaker. I would rate it a 3/5.

Reviewed on 25 Nov 2025

The Oliver Hotel

San Juan Antiguo

€542

per person

20 Jan - 26 Jan

found 1 day ago

Return direct flight included

Chicago (ORD) to San Juan (SJU)

9/10 Wonderful! (50 reviews)

Excelente habitación!!! Muy espaciosa y cómoda. Muy buena localización.

Reviewed on 25 Nov 2025

Tours & day trips

See all 233 activities

Puerto Rico: UTV and Can-Am Sightseeing Tours

Free cancellation available

Private & custom tours

See all 65 activities

Puerto Rico: UTV and Can-Am Sightseeing Tours

Free cancellation available

Water activities

See all 39 activities

Snorkel with Turtles, San Juan with Videos

Free cancellation available

Classes & workshops

See all 25 activities

Sunset Salsa Beach Class in San Juan

Free cancellation available

Attractions

See all 4 activities

Puerto Rico: The Beast Zipline at Toro Verde Adventure Park

Free cancellation available

Popular places to visit

Plaza de Armas

San Juan’s hub of civic life is also one of the most popular social destinations, where locals come to drink coffee and trade stories.

Catedral Basilica Menor de San Juan Bautista

5/5(1 review)

Discover the curious relics and gorgeous stained-glass windows of Old San Juan’s religious treasure, a 16th-century cathedral with a colorful history.

Paseo de la Princesa

During your trip to San Juan, you can search for that perfect souvenir at Paseo de la Princesa. Experience the area's fascinating museums and acclaimed art galleries.

La Fortaleza

5/5(1 review)

The official residence of the governor of Puerto Rico is a vast mansion and fortress that is open to the public on guided tours.

San Juan Gate

4.5/5(2 reviews)

Enter San Juan through the last remaining gateway from the city’s walls and discover the military history of its atmospheric Old Town.

Puerta de San Juan

Learn about the local history of San Juan when you take a trip to Puerta de San Juan. Experience the area's fascinating museums and acclaimed art galleries.