10 Things to See and Do in Chicago, Illinois

By: Anna Fleet

The Chicago skyline beckons visitors to a “windy city” where architecture, food, live music, art, and outdoor activities are plentiful. It’s difficult to narrow down the “must-do” activities in a city jam-packed with shopping, parks, panoramic views, gourmet pizza, and sports fans. However, we’ve done our very best to put together a list of ten things to see and do if you find yourself in Chicago, Illinois…


1. Tour Frank Lloyd Wright’s Home

Step into the shoes of the famous designer by visiting Frank Lloyd Wright’s private residence and architectural studio to discover where he spent the bulk of his career (1889 to 1909). The home features guided tours and history to preserve the famous artist’s memory and contributions to American architecture.

frank lloyd wright
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2. Catch a Game

Chicago is serious about its baseball so this town is the perfect one to catch a Cubs or White Sox ball game—and to snack on a world-famous Chicago-style hot dog.

Richard Cavalleri / Shutterstock.com

3. Navy Pier

Built in 1916, the scenic Navy Pier is a plethora of restaurants, shops, and live entertainment—including the famed Chicago Children’s Museum, Crystal Gardens botanical park, the Chicago Shakespeare Theater, and the Smith Museum of Stained Glass. You can also hop aboard a boat cruise at the nearby River East Plaza and enjoy a view of the stunning city skyline.

navy pier

4. Millennium Park

This massive 24.5-acre park in the heart of downtown Chicago is a visual masterpiece of architecture, sculpture, and landscape art. Take a stroll—and remember your camera!

chicago park
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5. Sears Tower

The Skydeck at Chicago’s famous Sears Tower offers unprecedented views of the city from one of the world’s highest buildings.

sears tower
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6. The Magnificent Mile

A shopper’s dream—this stretch of 460 shops includes brand-name favorites like Nike, American Girl, Crate & Barrel, Bloomingdale’s Fashion, not to mention a top-notch spa, salon, fitness club, several museums, and delectable spots to dine.

chicago skyline

7. The Art Institute of Chicago

Get a good dose of creative inspiration as you wander through famous French Impressionists, line drawings from Asia, European fine art, American photography and architectural drawings, Latin American textiles, and creations dating back as far as 3,000 B.C.

chicago art institute
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8. Have a Laugh

The laughs have been rolling out of Second City since 1959, when the Chicago landmark started hosting nightly comedy shows from famous names like John Belushi, Bill Murray, Gilda Radner, and Mike Myers.

second city
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9. Chicago Botanical Gardens

Explore the lush specialty living art at Chicago’s Botanical Garden. This 385-acre park features 23 blooming gardens amid charming islands, winding lakes, year-round festivals, and guided tours.

chicago botanical gardens


10. Eat your Heart Out

A trip to Chicago wouldn’t be complete without eating your way through the city’s superb delectable delights—including cheese steak, deep-dish pizza, and trendy restaurants with live music.

deep-dish pizza