Things to do in Chicago

Chicago for First-Time Visitors: A Guide to the Top Things to Do

A guide to Chicago's top attractions, restaurants, shopping areas and more

Top Things to Do in Chicago

Deep dish. Wrigley. Architecture tours. Don't miss these classic Chicago adventures.

Chicago for Sports Fanatics

A guide to all the best places to watch a game, buy team gear and brush up on sports history for teams across the board.

Chicago for a Guys Getaway

Gather up your best buds and hit up the Windy City for a boys only trip.

About Chicago

The Windy City, City of Big Shoulders, the Second City: Chicago has many nicknames, each stemming from history and personality. The city got its official name from the area’s Native Americans, who described it as “wild onion” because of the strong smell of onions growing in the previously swampy land. Since its establishment as a city in 1837, much has changed. No longer a swampland, the city’s motto “Urbs in Horto” (City in a Garden) still recalls its roots. As the third largest city in the country, Chicago is known for everything big: buildings, pizza, personalities. But there’s a sense of community unseen in other large cities. There’s a reason Frank Sinatra sang about Chicago being his kind of town: Even though it’s a big city, it’s always calling you “home.”

The City’s Culture

The rumors are true: Midwesterners truly are friendly people. And this applies even to Chicago. Need directions? Locals will stop and help you out and let you know their favorite spots to check out. Residents take pride in their arts and culture, which spreads throughout the city. We’re diverse and divided sometimes, but tell us an out-of-town sports team is better than ours, and we come together to stand up for even our losing teams. Sports fans in Chicago take that kind of thing seriously. Just like a phoenix rising from the ashes of the Great Chicago Fire, Chicagoans are a resilient and proud community. Chicagoans tough it out for 100-degree, humid summer days and negative-30 polar vortex wind chills, so they have no problem voicing strong opinions on what’s what.

Essential Experiences

One of Chicago’s biggest stars is its architecture, and architecture tours abound by foot, bicycle, Segway, boat and bus. Or get a lay of the land in and around Chicago atop Willis Tower’s Skydeck Chicago or the Hancock building’s 360 Chicago. During warm weather, Lake Michigan beaches beckon. Lounge in the sun, brave the chilly waters for a swim, join a beach volleyball game, charter a sailboat, or take a boat or kayak tour. The 18-mile Lakefront Path teems with cyclists, runners, dog-walkers and people out for leisurely, scenic strolls. World-class museums like the Art Institute of Chicago, Shedd Aquarium, Adler Planetarium, Field Museum and Museum of Science and Industry are perfect for culture-seekers and families. Chicago is also famous for its iconic foods like deep-dish pizza, hot dogs and prime steaks, but plenty of award-winning chefs have elevated the city’s dining experiences to four-star.

Where to Explore

As a city of neighborhoods—there are more than 70 of them—Chicago can be a fascinating exploration of various cultures and scenery. Some top spots to visit are all easily accessible. The downtown area includes the Loop business district, which sits right next to Millennium Park. Just north is the Magnificent Mile for stellar shopping, as well as River North where visitors find some of the best dining and nightlife. North of there is the Gold Coast, historically the poshest enclave in the city with designer shopping and high-end dining, as well as late-night bars for post-college crowds. Lincoln Park and Lakeview are known for tree-lined streets, award-winning restaurants and local shops. West of the city, Bucktown and Wicker Park are artsy areas for indie-owned shops and more dining gems.

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