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What to see & do in Chicago, the Best Big City in the U.S.

By Choose Chicago

What makes Chicago the country’s Best Big City? Famed restaurants, renowned museums, stunning outdoors, and so much more.

boats on the chicago river in chicago il with skyscrapers in the background
Credit: Ranvestel Photographic/Choose Chicago

Chicago is a city known for its world-class culture, electric big city buzz, and welcoming Midwestern spirit that makes visitors feel right at home.

Those are just a few of the many reasons that Chicago has been voted the Best Big City in the U.S. for an unprecedented nine years in a row by Condé Nast Traveler readers.

What makes Chicago the country’s Best Big City? There are so many reasons—famed restaurants, renowned museums, stunning outdoors, groundbreaking live music, accessible spaces, award-winning theatres, and iconic architecture—all within 77 vibrant and diverse neighborhoods.

Chicago’s world-class cultural scene comprises some of the world’s most famous museums, including the Art Institute of Chicago, ranked one of the top five museums on the planet by TripAdvisor. Visit the lakefront Museum Campus to explore the Field Museum, Shedd Aquarium, and the Adler Planetarium. And the Griffin Museum of Science and Industry is the largest science museum in the Western Hemisphere.

Chicago is the birthplace of improv (catch comedy’s rising stars at The Second City), electrified blues, Chicago-style jazz, and house music. Our innovative theatre scene includes everything from smash hits by Broadway in Chicago and Tony-Award-winning venues to storefront theatres producing cutting-edge new works.

Chicago’s always-evolving culinary landscape is one of the most awarded in the country, with 23 Michelin-starred restaurants and 55 Bib Gourmands, countless James Beard Awards, and international cuisines from all around the world.

No matter where you go, the city’s warm and welcoming spirit shines through. In Northalsted, you’ll find the country’s first official LGBTQ+ neighborhood that’s home to Chicago’s epic Pride celebrations each June. Chicago also strives to make its spaces accessible to all, including public transportation, museums, theatres, and beyond.

Be wowed by Chicago’s stunning architecture, including Art Decor beauties, soaring skyscrapers, and UNESCO World Heritage sites designed by Frank Lloyd Wright. Admire some of the city’s most iconic buildings on a scenic architecture cruise along the Lake Michigan shoreline or the Chicago River.

For more waterfront exploration, you can also hop in a kayak and paddle past the bustling Chicago Riverwalk, filled with alfresco cafes and eye-catching public art. Head to the lake to enjoy miles of parks, walking paths, and sandy beaches with skyline views.

There’s no shortage of iconic Chicago attractions—“The Bean” in Millennium Park, waterfront Navy Pier, SkyDeck Chicago in the Willis Tower (one of the world’s tallest buildings), 360 CHICAGO, shopping on The Magnificent Mile, Pullman National Monument, Buckingham Fountain, DuSable Black History Museum, and more.

Visitors will find a packed calendar of exciting events all year long, from magical holiday traditions like ZooLights and Millennium Park ice skating to major summer festivals like Lollapalooza, one of the most famous music events in the world.

Finally, you can’t leave Chicago without exploring the city’s rich tapestry of neighborhoods. These vibrant communities represent a diverse array of cultures, people, and experiences, from Chinatown to Bronzeville to Uptown and beyond.

Come discover what makes Chicago a city truly unlike any other.