22 days in Chicago & San Juan Itinerary

22 days in Chicago & San Juan Itinerary

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Plan created by another user.Make it yours

Route & dates

1
Chicago, United States
— 6 nights
2
San Juan, Puerto Rico
— 15 nights

6
nights
Chicago, United States

Chicago ©
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, take a stroll through The Magnificent Mile, try to win big at Horseshoe Hammond, and get curious at Museum of Science and Industry.

For traveler tips, other places to visit, maps, and other tourist information, go to the Chicago online travel route planner.

If you are flying in from United States, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In December, daytime highs in Chicago are °F, while nighttime lows are °F. On the 27th (Sun), wrap the sightseeing up by early afternoon so you can travel to San Juan.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trips

Horseshoe Hammond, Frank Lloyd Wright Home and Studio
Find places to stay Dec 21 — 27:
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Lincoln Park Zoo ©
Lincoln Park Zoo

15
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Explore the numerous day-trip ideas around San Juan: Zipline (in Rio Grande), El Yunque National Forest (El Portal Tropical Forest Center & El Yunque Rain Forest) and Ponce (Casa Wiechers-Villaronga, Museo de Arte de Ponce, &more). There's lots more to do: get to know the fascinating history of Old San Juan, trot along with a tour on horseback, walk around Parque Nacional de las Cavernas del Rio Camuy, and tour the pleasant surroundings at Condado Beach.

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 °F and lows about °F. Finish your sightseeing early on the 11th (Mon) to allow enough time to travel back home.

Things to do in San Juan

Parks Outdoors Tours

Side Trips

Ponce, El Yunque National Forest, Puerto Rico, Luquillo, Zipline
Find places to stay Dec 27 — Jan 11:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

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