Obrero Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Price found within the past 48 hours. Click for updated prices.
OLV Fifty Five - Adults Only
Condado
฿32,988
per person
2 Oct - 5 Oct
found 1 day ago
Return direct flight included
Chicago (ORD) to San Juan (SJU)
8.8/10 Excellent! (727 reviews)
Property was nice! Upscale boutique vibes. Service was wonderful. Be ready to pay for parking if you have a car. Great stay.
Reviewed on 16 Aug 2026
Where to stay in Obrero
Find the best Obrero areas and neighborhoods for the activities you enjoy most. Learn more about Obrero
Isla Verde
1 out of top 10 points of interest in this area
White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico.
Old San Juan
The interesting museums and waterfront views are top of the list for many visitors to Old San Juan. A stop by Port of San Juan or Castillo de San Cristobal might round out your trip.
Condado
1 out of top 10 points of interest in this area
Experience San Juan at its most modern in a chic neighborhood packed with high-end fashion shops, elegant casinos and popular restaurants.
Santurce
2 out of top 10 points of interest in this area
While you're in Santurce, take in top sights like Casino del Mar at La Concha Resort and jump on the metro at Sacred Heart Station to see more of the city.
Ocean Park
This cosmopolitan area of San Juan is a great place to experience the relaxed, contemporary culture of Puerto Rico.
Top hotels in Obrero
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
฿8,717
฿11,211 total
10 Sept - 11 Sept
includes taxes & fees
9.2/10 Wonderful! (3,275 reviews)
"Great experience!"
Reviewed on 17 Aug 2026
Fairmont El San Juan Hotel
6063 Isla Verde Avenue Carolina
Fully refundableReserve now, pay when you stay
฿11,567
฿16,518 total
31 Aug - 1 Sept
includes taxes & fees
The Condado Plaza Hotel
999 Ashford Avenue San Juan
Fully refundableReserve now, pay when you stay
฿4,865
฿6,567 total
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (2,744 reviews)
"It’s a beautiful place to be"
Reviewed on 16 Aug 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does an Obrero holiday package cost?
From as little as ฿25,846. Yes, you read that correctly. Our Obrero holiday packages are the quickest way to stretch your budget further. Combine your hotels, flights and rental car and explore this lively destination.
How do I get a cheap travel package to Obrero?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into an Obrero holiday package and save. Score even more bargains when you add extras such as experiences or tours to your booking. But that's not the only good part. You have the freedom to customize your holiday your own way. We offer over 550 airlines and 1,000,000 hotels throughout the world, so that everyone has a chance to travel and live out those holiday fantasies.
Where should I stay in Obrero?
Make sightseeing a breeze by staying someplace close to Obrero's big attractions. Luquillo Beach and Puerto Rico Convention Centre are two of the best in the area.
How far in advance should I book my Obrero holiday?
It's hard to pick the ideal time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available up to a year in advance. If you're booking last minute, fear not. Budget prices appear from time to time just weeks before departure dates.
What does an Expedia Obrero travel package include?
Travel packages include rental cars, flights and hotels, but you can mix and match them to create your dream Obrero holiday. You can also add on fun things like activities and tours once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking an Obrero travel package?
A travel package can be easier on the credit card than separately booking everything you need for your getaway. For example, bundle your hotels, flights and rental cars and save big. Whatever your holiday goals are, you're bound to find a package within your budget.
Can I choose my airline with an Obrero Expedia holiday package?
Yes, the choice is all yours. We have access to over 550 partner airlines all over the world, so you can tailor your Obrero escape according to your needs and budget.
If I'm not able to travel, can I cancel my Obrero holiday package?
Your situation can change in a flash, so yes. You may be able to change or cancel your Obrero holiday package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make changes, but your car rental company, airline or hotel may charge a fee. Looking for more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
Things to do
Underwater Sea Trek at Private Beach in San Juan
฿3,425
per traveller
92% of travellers recommend
Countryside Horseback Riding
฿5,593
per traveller
80% of travellers recommend
From Carolina: Horse Riding at a Private Ranch
฿3,739
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.