10 days in Chicago & San Juan Itinerary

10 days in Chicago & San Juan Itinerary

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10 days in Chicago & San Juan Itinerary

Start: Chicago, United States
1
Chicago, United States
— 4 nights
Fly:  7​h 45​min
2
San Juan, Puerto Rico
— 4 nights
Fly:  7​h 45​min
End: Chicago, United States

4
nights
Chicago, United States

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kids will appreciate attractions like Museum of Science and Industry and Shedd Aquarium. Step out of Chicago to go to Saint Joseph and see Silver Beach Carousel, which is approximately 1h 40 min away. There's still lots to do: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at 360 Chicago Observation Deck, shop like a local with The Magnificent Mile, and admire all the interesting features of Wrigley Field.

To see where to stay, photos, ratings, and more tourist information, you can read our Chicago trip maker site .

If you are flying in from United States, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In August, plan for daily highs up to 83°F, and evening lows to 67°F. Finish your sightseeing early on the 5th (Mon) to allow enough time to travel to San Juan.

Things to do in Chicago

Museums Childrens Museums Parks

Side Trips

Frank Lloyd Wright Home and Studio, Silver Beach Carousel
Find places to stay Aug 1 — 5:
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Shedd Aquarium ©
Shedd Aquarium

4
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Kids will appreciate attractions like Luquillo Beach and Condado Beach. Venture out of the city with trips to El Yunque Rain Forest (in El Yunque National Forest) and Museo de Arte de Ponce (in Ponce). Next up on the itinerary: get to know the fascinating history of Old San Juan, steep yourself in history at San Juan National Historic Site, pause for some photo ops at Paseo de los Presidentes, and take a memorable tour with Tours.

To find other places to visit, reviews, and other tourist information, refer to the San Juan day trip planner .

You can fly from Chicago to San Juan in 8 hours. Alternatively, you can do a combination of flight and car. The time zone changes from Central Standard Time to Atlantic Standard Time, which is usually a 2 hour difference. Traveling from Chicago in August, things will get somewhat warmer in San Juan: highs are around 89°F and lows about 78°F. Cap off your sightseeing on the 10th (Sat) early enough to travel back home.

Things to do in San Juan

Outdoors Parks Beaches

Side Trips

Museo de Arte de Ponce, El Yunque Rain Forest, Luquillo Beach
Find places to stay Aug 5 — 10:
Highlights from your plan
Old San Juan ©
Old San Juan
Luquillo Beach ©
Luquillo Beach
Condado Beach ©
Condado Beach

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