Top 10 Things to do in Chicago — with video

by GO GlobeHopper

Known by its nickname of the Windy City, Chicago is a vibrant metropolis in the state of Illinois known for its cutting-edge architecture, skyscraper skyline, and world-class art. Voted as the best big city in America five years in a row, there is something for everyone to enjoy. To help tourists create a “must-see-and-do” itinerary, we’ve compiled a list of the top 10 best things to do in Chicago.

⦿ To watch our video version of this article, visit our YouTube channel HERE and use the highest quality playback settings. Or, keep reading for valuable information and links.


Stroll Through Millennium Park

Sometimes referred to as Chicago’s front yard, Millennium Park sits in the heart of downtown Chicago. More than just a spot where tourists can visit for a photo-op, this park tells Chicago’s story.

Millennium Park should be on every traveler’s bucket list when visiting Chicago. The area is home to interesting architecture, stunning art, and plenty of green space. It is also where many tourists go to see the Crown Fountain, and the world-famous art piece Cloud Gate – better known as The Bean. In order to learn more about Millennium Park, the City of Chicago has free audio tours with history lessons, which can be downloaded here.


Visit the Art Institute of Chicago

Protected by two bronze lions on either side of its steps is the Art Institute of Chicago. This gallery is one of the world’s oldest and largest museums with a permanent collection of more than 300,000 pieces of art and artifacts.  Given so much to see, it is recommended to allow at least half a day to get through it.

World-famous works such as Vincent van Gogh’s The Bedroom, American Gothic by Grant Wood, and Water Lilies by Claude Monet reside here so there’s something for everyone from the casual tourist to the art fan.  Travelers to the city won’t want to pass up a visit to the Art Institute of Chicago.


Drop by Navy Pier

Navy Pier is one of Chicago’s top attractions. Located on the shores of Lake Michigan, this spot is open to tourists and locals year-round, but the best time to visit is in the summer. This is perfect for kids because it has plenty of exciting activities.

One of the more popular attractions is the Centennial Wheel, a 200-foot Ferris wheel. The Pepsi Wave Swinger is a musical carousel and Amazing Chicago’s Funhouse Maze is a 4,000-square-foot interactive funhouse. Navy Pier isn’t just for children; there are numerous restaurants, bars, and even the Navy Pier Beer Garden for adults to enjoy.


Hang with Animals at Lincoln Park Zoo

Found right in the center of Lincoln Park is the Lincoln Park Zoo. This zoo is the fourth oldest in North America and offers year-round free entry for the whole family to enjoy.

The Lincoln Park Zoo has approximately 1,100 animals from 200 different species. The exhibits include big cats, zebras, sloths, gorillas, reptiles, and many more. The zoo also has over 1,200 plant species that provide the grounds with vibrant colors, and fresh scents, plus native birds, fish, insects, and frogs. The Lincoln Park Zoo is a great family-friendly place to visit while saving a few bucks.


Relax on the River Walk

Located on the south bank of the Chicago River, the pedestrian-friendly Chicago Riverwalk provides a scenic stroll that stretches 1.25 miles from Lake Michigan to Lake Street.

Along the way, you’ll discover intimate coves, charming cafes, wineries, and bars.  Plus, there are public art displays, monuments, and museums.

Best of all, locals and visitors alike can access the water with urban kayaks and several different types of boat excursions.


Catch a Baseball Game

Baseball is an American classic, so why not go to the oldest ballpark in the National League when visiting Chicago? Wrigley Field is a living monument to baseball’s past and the place the Chicago Cubs call home.

Visitors and locals can go to a game and get some great seats during the season for less than $50.

During the offseason, Wrigley Field offers daily tours that take guests to the Cub’s dugout, the press box, the field, the visitor’s clubhouse, and many more iconic spots.


Explore Chicago’s Field Museum

An excellent place for historians is the Field Museum of Natural History. This gallery attracts 1.65 million visitors every year and is one of the world’s largest museums of natural history.

With close to 40 million artifacts and specimens in the museum’s collection, the permanent exhibitions include cultures across the globe, fossils, and space, to name a few.

There are also traveling exhibitions that come and go, so be sure to look up current exhibits here.


Face Your Fears at the Willis Tower

Formerly known as the Sears Tower, the Willis Tower is a 108-story skyscraper that stands 1,450 feet tall.

The Skydeck is located on the 103rd floor and is where The Ledge is situated. Only the bravest guests can step into The Ledge, a glass box extending about 4.3 feet out from the Skydeck. Not only can visitors see breathtaking views of the city, but on particularly clear days, the states of Illinois, Indiana, Michigan, and Wisconsin can be seen too.

Since it is such a popular tourist destination, it is highly advised to book tickets in advance to avoid missing out.


Stop by the Chicago Cultural Center

The Chicago Cultural Center is a Chicago Landmark building and one of the city’s most popular attractions. It is considered one of the most comprehensive showcases of art in all of the United States. It features over 1,000 events and exhibitions that include performing and visual arts, as well as films and lectures, all of which are free to the public.

The Tiffany Dome ­– the world’s largest glass dome that features 30,000 pieces of stained glass – is found at the Chicago Cultural Center and was made by America’s top mosaicist Jacob A. Holzer.


See a Show at the Chicago Theatre

The Chicago Theatre was the first large and luxurious movie theater in America. Constructed in 1921, it is seven stories high and holds up to 3,600 people in its auditorium. Musical legends like Duke Ellington and Aretha Franklin, as well as comedy powerhouses like Robin Williams and Chris Rock, have all performed on the stage.

The Chicago Theatre marquee, which often appears in films and television, is a distinctive emblem of Chicago and makes the theater unmissable. Visitors can also go on a behind-the-scenes tour of this magnificent and historic building, where guests learn about the history and the artists who performed here.


While you’re in the Windy City, don’t forget to enjoy a slice of Chicago-style deep-dish pizza. There are several places throughout the city to get a slice of this saucy, cheesy pizza, but some of the best are Lou Malnati’s, Burt’s Place, and Giordano’s.

⦿ If you’re looking for an exciting and centrally-located place to stay in Chicago, consider Staypineapple The Loop.  To watch our video tour of the hotel, click here.


Photo Credits:
Lead Photo – Pedro Lastra on Unsplash
The Bean – Benjamin Rascoe on Unsplash
Art Institute of Chicago Lion – Wikimedia – by Teemu008 – Licence CC Attribution-Share Alike 2.0 Generic
Navy Pier – islandworks on Pixabay
Lincoln Park Zoo – Matthew Mazzei on Unsplash
Wrigley Field – Blake Guidry on Unsplash
Field Museum – Mana5280 on Unsplash
Willis Tower – Noel Forte on Unsplash
Giordano’s Pizza – Matt Antonioli on Unsplash
Chicago Cultural Center – Alicja Podstolska on Unsplash
Chicago Theater – Maarten van den Heuvel on Unsplash

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