10 days in Chicago & San Juan Itinerary

10 days in Chicago & San Juan Itinerary

Created using Inspirock trip planner

Make it your trip
1
Chicago, United States
— 4 nights
Fly
2
San Juan, Puerto Rico
— 4 nights
Fly

S M T W T F S
28
29
30
31
1
2
3
4
5
6
7
8
9
10

Chicago, United States

— 4 nights

Windy City

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 take a leisurely stroll along Navy Pier.

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 Gary Chicago International 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 catch the flight to San Juan.

Things to do in Chicago

Museums · Childrens Museums · Parks · Zoos & Aquariums

Side Trips

San Juan, Puerto Rico

— 4 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.
Bring the kids along to Old San Juan and Canyoning & Rappelling Tours. Change things up with these side-trips from San Juan: Luquillo Beach (in Luquillo), Museo de Arte de Ponce (in Ponce) and El Yunque Rain Forest (in El Yunque National Forest). Next up on the itinerary: enjoy the sand and surf at Condado Beach, get to know the fascinating history of Sitio Histórico de San Juan, contemplate the long history of Catedral Basilica Menor de San Juan Bautista, and get interesting insight from Tours.

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 fly back home.

Things to do in San Juan

Outdoors · Parks · Beaches · Tours

Side Trips