22 days in Chicago & San Juan Itinerary

22 days in Chicago & San Juan Itinerary

Created using Inspirock trip planner

Make it your trip
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Chicago, United States
— 6 nights
Fly
2
San Juan, Puerto Rico
— 15 nights
Fly

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Chicago, United States

— 6 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, learn more about the world around you at Field Museum, appreciate the history behind Cloud Gate, and try your luck at Horseshoe Hammond.

For ratings, traveler tips, reviews, and tourist information, read Chicago travel planner.

If you are flying in from United States, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In December in Chicago, expect temperatures between 38°F during the day and 26°F at night. On the 27th (Sun), wrap the sightseeing up by early afternoon so you can fly to San Juan.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums

Side Trips

Find places to stay Dec 21 — 27:

San Juan, Puerto Rico

— 15 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Venture out of the city with trips to El Yunque National Forest (El Portal Tropical Forest Center & El Yunque Rain Forest), Ponce (Casa Wiechers-Villaronga, Museo de Arte de Ponce, &more) and Zipline (in Rio Grande). There's lots more to do: visit Old San Juan, Head underground at Parque Nacional de las Cavernas del Rio Camuy, scramble along the landscape with a canyoning and rapelling tour, and enjoy the sand and surf at Playa Luquillo.

To find maps, photos, and tourist information, read our San Juan day trip planner.

Getting from Chicago to San Juan by flight takes about 8 hours. The time zone difference moving from Central Standard Time to Atlantic Standard Time is 2 hours. Traveling from Chicago in December, things will get much warmer in San Juan: highs are around 85°F and lows about 75°F. Finish your sightseeing early on the 11th (Mon) to allow enough time to fly back home.

Things to do in San Juan

Outdoors · Parks · Tours · Historic Sites

Side Trips

Find places to stay Dec 27 — Jan 11: