Chicago Travel Guide | Undercover Tourist

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Chicago City Guide

Overview

With an abundance of culture, amazing food and year-round sporting events, Chicago is an easy pick for a family vacation.

The Windy City is the third most populous city in the U.S., serving as a bustling international hub for commerce, art and technology. Located on the shores of freshwater Lake Michigan, Chicago was incorporated as a city in 1837. Known for its bold architecture (as seen at Willis Tower), public art installations (such as Millennium Park) and entertainment (Navy Pier), there’s something for every froggy in Chicago.

Best Time to Visit

You’ll find the best weather in April, May, September and October when temperatures are pleasant, but not too hot. Still, be sure to check the forecast before your trip so there are no surprises!

What We Love

552 interactive parks that include fun features such as fountains, playgrounds, play gardens and bike trails
Culture for all ages (outside of the abundance of street art such as The Bean, you’ll find museums, the Shedd Aquarium and the free Lincoln Park Zoo, to name a few)
Popular sports stops, including the Chicago Cubs at the iconic Wrigley Field, the White Sox, the Bears (football), the Bulls (basketball) and the Blackhawks (hockey)
Delicious eats (deep-dish pizza, anyone?)
Easy to navigate using public transportation

Fun Facts About Chicago

Chicago is the second most visited city in the U.S., second only to NYC.
The Art Institute of Chicago holds the largest collection of Impressionist paintings outside the Louvre.
Shedd Aquarium is home to 32,000 animals.
Walt Disney was born in Chicago.
Chicago is home to many inventions, including the zipper (1851), spray paint (1949) and the Ferris wheel (1893).

Be sure to check out Chicago from a different perspective! You can get a bird’s-eye view of the city from observation decks at two of the tallest buildings in the city: Willis Tower (formerly Sears Tower) and the John Hancock Building.