6 days in Puerto Rico & Chicago Itinerary

6 days in Puerto Rico & Chicago Itinerary

Make it your trip
Fly
1
Culebra, Puerto Rico
— 1 night
Fly
2
Orocovis, Puerto Rico
— 1 night
Drive
3
Ponce, Puerto Rico
— 1 night
Drive
4
Rincon, Puerto Rico
— 1 night
Drive
5
San Juan, Puerto Rico
— 1 day
Fly
6
Chicago, United States
— 1 night

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Culebra, Puerto Rico — 1 night

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
On the 4th (Sat), enjoy the sand and surf at Flamenco Beach.

For other places to visit, maps, photos, and tourist information, refer to the Culebra online trip planner.

Chicago, USA to Culebra is an approximately 10-hour flight. Traveling from Chicago to Culebra, you'll lose 2 hours due to the time zone difference. Prepare for much hotter weather when traveling from Chicago in December: high temperatures in Culebra hover around 85°F and lows are around 75°F. Wrap up your sightseeing on the 4th (Sat) to allow time to fly to Orocovis.
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Outdoors · Beaches · Parks
Find places to stay Dec 3 — 4:
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Orocovis, Puerto Rico — 1 night

Orocovis is a municipality of Puerto Rico located in the Central Mountain Range, north of Villalba and Coamo; south of Morovis and Corozal; southeast of Ciales; east of Jayuya; and west of Barranquitas. You've now added Catarata Chorro de Dona Juana to your itinerary. Kick off your visit on the 5th (Sun): admire the sheer force of Catarata Chorro de Dona Juana and then play a few rounds at Bahia Beach Plantation.

To find reviews, other places to visit, ratings, and more tourist information, go to the Orocovis trip builder app.

Getting from Culebra to Orocovis by flight takes about 2.5 hours. Other options: do a combination of ferry and car. In December, Orocovis is a bit cooler than Culebra - with highs of 80°F and lows of 70°F. Wrap up your sightseeing on the 5th (Sun) to allow time to drive to Ponce.
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Nature · Outdoors · Golf · Parks
Side Trip
Find places to stay Dec 4 — 5:
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Ponce, Puerto Rico — 1 night

Ponce is both a city and a municipality in the southern part of Puerto Rico. Kick off your visit on the 6th (Mon): examine the collection at Parque de Bombas and then take an in-depth tour of Museo de Arte de Ponce.

To find ratings and other tourist information, read our Ponce online road trip planner.

You can drive from Orocovis to Ponce in 1.5 hours. Expect a daytime high around 80°F in December, and nighttime lows around 70°F. Wrap up your sightseeing on the 6th (Mon) early enough to drive to Rincon.
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Museums
Find places to stay Dec 5 — 6:
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Rincon, Puerto Rico — 1 night

A seaside playground in the Caribbean, Rincon was a small agricultural and fishing town until it hosted the 1968 World Surfing Championship.
For photos, where to stay, and more tourist information, use the Rincon tour itinerary planner.

Traveling by car from Ponce to Rincon takes 1.5 hours. Alternatively, you can do a combination of shuttle, flight, and taxi. Expect somewhat warmer evenings in Rincon when traveling from Ponce in December, with lows around 77°F. On the 7th (Tue), you'll travel to San Juan.
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Outdoors · Parks · Tours · Wildlife
Find places to stay Dec 6 — 7:
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San Juan, Puerto Rico — 1 day

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Start off your visit on the 7th (Tue): get to know the fascinating history of Sitio Histórico de San Juan and then get to know the fascinating history of Old San Juan.

To see maps, reviews, other places to visit, and more tourist information, read our San Juan itinerary planner.

Drive from Rincon to San Juan in 2 hours. Alternatively, you can fly; or do a combination of car and shuttle. In December, daily temperatures in San Juan can reach 85°F, while at night they dip to 75°F. Finish your sightseeing early on the 7th (Tue) so you can fly to Chicago.
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Historic Sites · Neighborhoods
Find places to stay Dec 7 — 8:
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Chicago, United States — 1 night

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 8th (Wed), get curious at Museum of Science and Industry, then walk around Millennium Park, then admire the striking features of Reliance Building, and finally don't miss a visit to Skydeck Chicago - Willis Tower.

Before you visit Chicago, use our trip planner to discover what you can do and see there.

You can fly from San Juan to Chicago in 8 hours. The time zone difference when traveling from San Juan to Chicago is minus 2 hours. Expect much colder temperatures when traveling from San Juan in December; daily highs in Chicago reach 38°F and lows reach 26°F. Cap off your sightseeing on the 8th (Wed) early enough to travel back home.
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Museums · Childrens Museums · Parks
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Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Kayaking & Canoeing
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.
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