10 days in Chicago & San Juan Itinerary

10 days in Chicago & San Juan Itinerary

Created using Inspirock trip planner

Plan created by another user.Make it yours

Route & dates

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

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 Lincoln Park Zoo. 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 °F during the day and °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
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: Museo de Arte de Ponce (in Ponce) and El Yunque Rain Forest (in El Yunque National Forest). And it doesn't end there: enjoy the sand and surf at Condado Beach, appreciate the extensive heritage of Sitio Histórico de San Juan, take a memorable tour with Tours, and skim along the rocks with a canyoning and rapelling tour.

To see ratings, more things to do, traveler tips, and more tourist information, you can read our San Juan online travel planner.

You can fly from Chicago to San Juan in 8 hours. The time zone difference moving from Central Standard Time to Atlantic Standard Time is 2 hours. In August, San Juan is a bit warmer than Chicago - with highs of °F and lows of °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, Luquillo Beach, El Yunque Rain Forest
Highlights from your plan
Old San Juan ©
Old San Juan
Luquillo Beach ©
Luquillo Beach
Condado Beach ©
Condado Beach

Similar Plans

11 days in Chicago BY A USER FROM TURKEY July, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: July, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 11 days in Chicago & Denver BY A USER FROM INDIA July, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: July, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 11 days in Chicago & Racine BY A USER FROM ARGENTINA June, culture, outdoors, relaxing, romantic, beaches, museums, shopping, popular & hidden gems Preferences: June, culture, outdoors, relaxing, romantic, beaches, museums, shopping Attraction style: Popular & hidden gems Pace: Medium 14 days in Chicago, Washington DC & New York City BY A USER FROM UNITED KINGDOM June, teens, kids, culture, outdoors, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: June, teens, kids, culture, outdoors, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 18 days in United States BY A USER FROM UNITED STATES July, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, fast-paced, popular & hidden gems Preferences: July, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Fast-paced 12 days in Chicago BY A USER FROM UNITED ARAB EMIRATES October, culture, outdoors, relaxing, beaches, historic sites, shopping, popular sights Preferences: October, culture, outdoors, relaxing, beaches, historic sites, shopping Attraction style: Popular sights Pace: Medium 8 days in Chicago BY A USER FROM MEXICO June, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: June, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 8 days in Chicago BY A USER FROM CANADA June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 15 days in Chicago BY A USER FROM MONGOLIA June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 19 days in United States BY A USER FROM TURKEY September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium
See more plans