Top Chicago Sights and Attractions

The diversity of Chicago attractions means that there’s something for everyone in this vast city where art, culture, history, entertainment, and education intersect. Some of the best museums in the world are located in Chicago, as well as some of the best parks and architectural feats.

At Smart Destinations, we want you to enjoy your Chicago vacation to the fullest. That’s why we are doing our best to make sure you see the top Chicago sights and attractions while you’re in the Windy City. Take a look at the best of what’s around so you can decide where your Chicago vacation will take your family.

Art Institute of Chicago

Currently the nation’s second largest art museum, the Art Institute of Chicago encourages creativity in every form. From paintings by the old masters, like Seurat and Rembrandt, to the most modern innovations in architecture and design, the Art Institute of Chicago encompasses all that is art. Make sure you spend time in the Modern Wing, where you’ll find Picasso’s Old Guitarist and O’Keefe’s Black Cross as well as contemporary American artists like Jackson Pollock, Joan Mitchell, Jasper Jones, and Larry Rivers.

Grant Park & Millennium Park

Located between Michigan Avenue and Lake Michigan, Grant Park is a large, public park in the center of downtown Chicago. The geometrically designed park, featuring wide tree-lined paths, sprawling sections of grass, and a variety of monuments is a popular spot for locals and tourists to relax on the lawns. It’s also the home to Buckingham Fountain, one of the largest fountains in the world which presents an hourly 20-minute water display including music, coreographed sprays, and colorful lights.

Millennium Park is the newest addition to Grant Park, located in the northeastern corner, and it is state of the art in every way. The beautiful flower gardens, modern design, and public art displays have rendered it quite the attraction in Chicago. You probably are familiar with Cloud Gate, the enormous bean-shaped shiny structure (and park entrance) designed to reflect Chicago’s magnificent skyline. The Pritzker Pavillion, an outdoor theater known for its super-contemporary design hosts live music at least once a week, drawing even more attention to the Park.

Navy Pier

On the banks of Lake Michigan, the Navy Pier is one of the most iconic Chicago attractions. Known as “Chicago’s lakefront playground,” Navy Pier is the number one mid-west tourist attraction, drawing 8.6 million visitors to the premises each year! Part of the reason for this is that there’s so much to do on the Pier. Ride the 150-foot Ferris wheel, eat at the Billy Goat Tavern or Haagen Dazs Café, see the Cirque Shanghai, get your thrills on the old-fashioned Wave Swinger, putt your way around the mini golf course, explore the abundance of outdoor art, sail on the historic Tall Ship Windy, or see a theatrical production at the Chicago Shakespeare Theater or the IMAX cinema.

Shedd Aquarium

In an area known as Museum Campus, Shedd Aquarium is one of several world-class museums—and undoubtedly one of everyone’s favorites. It’s the largest indoor aquarium in the world, featuring seven unique exhibits that recreate habitats around the world. The Shedd is home to giant octopuses, tiny mantella frogs, beluga whales, dolphins, sea otters, sea lions moon jellies, sea stars, blue iguanas, parrot fish, anacondas, sting rays, and many more fascinating creatures.

Skydeck Chicago – Willis Tower

Formerly known as the Sears Tower, the newly-named Willis Tower is still the tallest building in the entire western hemisphere and perhaps the most famous of all Chicago attractions. At the top of the 1,353-foot structure, you’ll see breathtaking panoramic views of Chicago from the incredible all-glass balcony known as “the Ledge” or the Skydeck Observatory. On a clear day, you can see all the way to Indiana or Wisconsin!


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