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, parks, and nightlife. Your plan 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 · Historic Sites

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.
Explore the numerous day-trip ideas around San Juan: El Yunque National Forest (El Portal Tropical Forest Center & El Yunque Rain Forest), Zipline (in Rio Grande) and Ponce (Casa Wiechers-Villaronga, Museo de Arte de Ponce, &more). Next up on the itinerary: appreciate the extensive heritage of Old San Juan, trot along with a tour on horseback, explore the fascinating underground world of Parque Nacional de las Cavernas del Rio Camuy, and skim along the rocks with a canyoning and rapelling tour.

For reviews, other places to visit, photos, and more tourist information, read San Juan trip builder site.

Traveling by flight from Chicago to San Juan takes 8 hours. The time zone changes from Central Standard Time to Atlantic Standard Time, which is usually a 2 hour difference. Traveling from Chicago in December, things will get much hotter in San Juan: highs are around 85°F and lows about 75°F. Cap off your sightseeing on the 11th (Mon) early enough to catch the flight back home.

Things to do in San Juan

Outdoors · Parks · Tours · Historic Sites

Side Trips

Find places to stay Dec 27 — Jan 11: