10 days in Chicago & San Juan Itinerary

10 days in Chicago & San Juan Itinerary

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Route & dates

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.
Bring the kids along to The Art Institute of Chicago and Millennium Park. Change things up with a short trip to Silver Beach Carousel in Saint Joseph (about 1h 40 min away). And it doesn't end there: catch a live event at Wrigley Field, admire nature's wide array of creatures at Shedd Aquarium, appreciate the history behind Cloud Gate, and enjoy breathtaking views from Skydeck Chicago - Willis Tower.

For more things to do, reviews, other places to visit, and other tourist information, use the Chicago online road trip 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 August in Chicago, expect temperatures between 83°F during the day and 67°F at night. Cap off your sightseeing on the 5th (Mon) early enough to travel to San Juan.

Things to do in Chicago

Museums Childrens Museums Parks

Side Trips

Silver Beach Carousel, Frank Lloyd Wright Home and Studio
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.
Bring the kids along to Old San Juan and Luquillo Beach. Change things up with these side-trips from San Juan: El Yunque Rain Forest (in El Yunque National Forest) and Museo de Arte de Ponce (in Ponce). Next up on the itinerary: enjoy the sand and surf at Condado Beach, skim along the rocks with a canyoning and rapelling tour, get interesting insight from Tours, and contemplate the long history of Sitio Histórico de San Juan.

To see ratings, traveler tips, and more tourist information, you can read our San Juan trip maker site.

You can fly from Chicago to San Juan in 8 hours. Traveling from Chicago to San Juan, you'll lose 2 hours due to the time zone difference. Expect somewhat warmer temperatures when traveling from Chicago in August; daily highs in San Juan reach 89°F and lows reach 78°F. Finish your sightseeing early on the 10th (Sat) so you can travel back home.

Things to do in San Juan

Outdoors Parks Beaches

Side Trips

El Yunque Rain Forest, Luquillo Beach, Museo de Arte de Ponce
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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