See Chicago

Must-see sights and activities in the Windy City

Chicago bills itself as a city that feels like home. Rich in history, art, culture and culinary delights, the city of Chicago welcomes all walks of life with a breadth of attractions and activities. From architectural masterpieces and enthralling museums, to theater and dining, here is your guide to sightseeing in Chicago.

Catch A Show

Chicago has a robust theatre scene.

Fearless is the word most used to describe Chicago theater. The adjective is a nod to the soul of the city, home to more than 200 stages, including five regional Tony Award-winning theaters (more than any other city in the nation can say, no offense to The Great White Way). Acclaimed productions aside, Chicago performance is, perhaps, best known for its laughs. Practically a springboard for Saturday Night Live stardom, Chicago is where the budding comedy masters at The Second City shine. One of the world’s premier comedy clubs and school of improvisation, The Second City has turned out scores of celebrities, such as Tina Fey and Amy Poehler. It’s worth getting tickets just to say you saw them before they were famous.

See The Bean

The famous Chicago Bean sculpture reflects the night skyline.

Cloud Gate, aka “The Bean,” instantly became one of Chicago’s most popular attractions when it was unveiled in 2004. Located in Millennium Park, the lakefront park in Chicago’s downtown Loop, the 33-feet high, 42-feet wide public art installation reflects the city’s famous skyline and the surrounding green space in its 168 massive steel plates. Its curved, oblong shape earned it the nickname “The Bean.” While it’s cool to look at, The Bean isn’t the only reason to visit Millennium Park. The park is home to state-of-the-art architecture, landscape design and artwork that provides the backdrop for hundreds of free cultural programs including concerts, exhibitions, tours and family activities. Don’t leave without checking out the interactive Crown Fountain.

Stroll The Chicago River

Watching the Chicago River Bridge lift is a top attraction. (Photos courtesy of Choose Chicago)

In less than 10 minutes, you can hoof it from The Bean to the iconic Chicago Riverwalk. It is without a doubt one of the most tourist heavy destinations, but a worthwhile visit all things considered. The Riverwalk has a little something for everyone: plenty of shopping, dining, kayaking, fishing and public artwork, you name it and you can find it on the river. While you’re there stop into the McCormick Bridgehouse & Chicago River Museum for the inside scoop on the river and its world famous movable bridges.


Head To The Museums

Aerial view of Museum Campus

Speaking of museums, Chicago has no shortage of cultural centers. These aren’t the stuffy types, either. Extending out into Lake Michigan from its Museum Campus home, Adler Planetarium allows guests to transcend space and time. Its theater programs and exhibits are nothing short of spectacular. The Center for Intuitive and Outsider Art, The Art Institute of Chicago, Field Museum of Natural History and Peggy Notebaert Nature Museum are also worth hitting up.

Eat Up

Chicago is a foodie destination.

Chicago’s dining scene reflects the city’s diversity. From comfort food and dive bars to international flavors and Michelin-starred restaurants, time spent eating in Chicago is well spent. If brunch is what you seek, Beatnik & Beatnik on the River, with locations in West Town and The Loop, is a stellar choice. The eclectic restaurant’s menu takes cues from Asia, Mexico, the Middle East, South America and beyond. The curry fried chicken sandwich is not to be missed. For upscale dining, Alinea in the Lincoln Park neighborhood has the honor of being the city’s only three-starred Michelin restaurant in 2020. While you’re in town, settle the great New York versus Chicago pizza debate. Pequod’s Pizza with outposts, in Morton Grove and Lincoln Park, is unofficial reigning champ among locals for best deep dish pizza, according to Time Out Magazine.

Visit Navy Pier

Navy Pier’s ferris wheel is an iconic part of the Chicago skyline. (Image by Quinn Kampschroer from Pixabay)

Loving referred to as “People’s Pier,” this landmark showcases more than 50 acres of parks, restaurants, attractions, retail shops, sightseeing and dining cruise boats, exposition facilities and more. In honor of its 100th anniversary in 2016, the park unveiled several new attractions, including the Centennial Wheel. Now an iconic part of the Chicago skyline, the ferris wheel offers visitors unparalleled, 360-degree views of the city and Lake Michigan.

Click here to see more from LIW‘s travel coverage of Chicago.

Cyndi Zaweski
Cyndi Zaweski is the former editor of Anton Media Group's special sections.

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