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Chicago – The Complete Activity Guide

Chicago Skyline

Chicago, the “Windy City,” is one of the top most visited cities in the nation. The third-most populous city in the United States is home to over 2.7 million residents and lots of things to do on a business trip or vacation.   

Chicago lake frontCloud Gate is a public sculpture by Indian-born British artist Sir Anish Kapoor, that is the centerpiece of AT&T Plaza at Millennium Park in the Loop community area of Chicago, Illinois

Must-See Places:

Chicago has plenty of parks and places that you have to go to while you’re in town.  Millennium Park is home to some of the city’s best art and architecture (including the famous Bean), gardens and landscapes, and free events and exhibitions.  Navy Pier sits right on Lake Michigan and has all different restaurants, shops and attractions, like the Centennial Ferris Wheel.  The Shedd Aquarium not only has amazing architecture and a global animal collection, but they also are leaders in animal and environmental care.  Skydeck Chicago sits at the top of Willis Tower, and welcomes visitors out onto the “Ledge” where you can get a one of a kind view of the city of Chicago.  The Tribune Tower is widely regarded as “the most beautiful building in the world,” because of its gorgeous architecture that includes actual pieces of other famous structures, including rock from the Alamo, the Colosseum and the Great Wall of China.



Of course, the city that invented the Twinkie is widely regarded as one of the best cities with the best food in the United States. With celebrity chefs, world-renowned restaurants and ethnic dining from all over the globe, Chicago is known for a variety of food.  Most sought out is deep dish pizza, and the original can be found at Uno Pizzeria & Grill.  Chicago is also known for its brunch scene, where there are plenty of restaurants to ensure that the most important meal of the day is skipped. The Chicago style hot dog was invented in – you guessed it – Chicago, and the best can be found at Portillo’s.  With 26 Michelin ranked restaurants and 52 Bib Gourmand ranked restaurants, you definitely will not go hungry.Baseball field


Sporting News has named Chicago the “Best Sports City” three separate times, which shouldn’t come as a surprise, since Chicago is one of only 10 US cities to have a sports team in all five of the major sports (baseball, football, basketball, hockey and soccer).  If you’re a baseball fan, catch a game at Wrigley Field, where the Chicago Cubs play, or at Guaranteed Rate Field, where the Chicago White Sox play.  The Chicago Bears play football at Soldier Field, and the Chicago Fire plays soccer at Toyota Park.  Both the Chicago Bulls, basketball, and the Chicago Blackhawks, hockey, play their games at United Center. Chicago also showcases female athletes with both the Chicago Sky, basketball, that plays at Allstate Arena and the Chicago Red Stars, soccer, that play at Toyota Park.

Inside of a Museum


Chicago’s got museums for history, nature and culture all covered.  The Field Museum of Natural History has over 30 permanent exhibitions full of biological and anthropological artifacts.  The Museum of Science and Industry is one of the largest science museums in the world that aims to motivate and inspire every “inventive genius.”  The Adler Planetarium has exhibits all about space and space exploration, with the mission of sparking excitement and curiosity.

Double Decker Bus


Chicago is a city with a lot of history, and there are a variety of bus and boat tours to take you around to learn more.  The Big Bus Chicago Tour takes you all over the city and allows you to hop on and hop off as you please.  This is perfect for getting all around Chicago and exploring at your own pace.  The Crime and Mob Bus Tour stops at famous crime scenes, takes you by famous landmarks and tells you all about different famous criminals and mobsters in Chicago, like Al Capone, the Chicago Mob and the Chicago Black Sox.  The city of Chicago is known for its beautiful and innovative architecture, and the Chicago Architecture River Cruise shows you why the city’s buildings rank third in the world. The Chicago Segway Tour teaches you how to ride a segway and then takes you for a ride through some of Chicago’s most famous neighborhoods.

Sculpture portraying Grant Wood’s American Gothic characters


As one of the “12 Best Cities in the US to See Art,” Chicago is the place for every art lover. The Art Institute of Chicago is one of the oldest and largest art museums in the nation, and is home to a large number of famous paintings, including Vincent Van Gogh’s Self Portrait, Pablo Picasso’s Old Guitarist and Grant Wood’s American Gothic.  The Chicago Theater is a famous landmark known for its beautiful architecture and the organ inside that has the ability to sound like an entire orchestra.  In the Loop, there is the Chicago Picasso, a sculpture by Picasso himself, that has become a famous landmark, even though no one quite knows what it is supposed to be a sculpture of.  Guesses range from a bird to an aardvark to an Afghan hound to the Egyptian deity Anubis, so check it out and try to guess for yourself. Chicago is also the birthplace of improvisational comedy, so it’s necessary to see a show while you’re in town. There are a variety of different comedy clubs all over town, but a few include The Second City, iOTheater and Laugh Factory.

shopping bags


From designer stores to outlet malls, Chicago has shopping for everyone. The most famous place to hit while in town is the Magnificent Mile on Michigan Avenue. With three malls and stores like Nike, Chanel and Nordstrom, you could spend your whole trip walking up and down this street. The Fashion Outlets are best if you like getting a bang for your buck.  With shops from worldly designers to big department stores, you’ll be able to find deals everywhere you look.


Sources: EXPLORE CHICAGO’S RESTAURANT SCENE, Things to Do in ChicagoShopping in Chicago: sweet spots abound all around town