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How to Beat the Crowds in Chicago

Enjoy a tranquil visit to Chicago with these travel tips.

How to Beat the Crowds in Chicago
Hi, I'm Claire!

Claire Bullen is an award-winning food, drinks, and travel writer and editor who has lived and worked in Chicago, Philadelphia, New York, Paris, and London. She is the author of The Beer Lover's Table: Seasonal Recipes and Modern Beer Pairings, and the editor at GoodBeerHunting.com. Her writing has also appeared in Time Out New York, The Daily Meal, Pellicle Magazine, and beyond.

As a top US destination, Chicago welcomes more than 50 million visitors each year. That said, you can still enjoy a tranquil visit to the Windy City. From exploring by boat to discovering Chicago’s local restaurants and neighborhoods, here’s how to beat the crowds.

Explore the city by boat

A boat plies Chicago's waters on a sunny day in Illinois.
A photo of downtown Chicago.Foto: f11photo / Shutterstock

Cruise through downtown along the river.

Instead of fighting the crowds of Magnificent Mile, take to the Chicago River or Lake Michigan, from which you can admire the Windy City’s skyscrapers and skyline without the crowds on an open-top boat tour; head out at sunset for the best views.

Venture beyond the loop

A fountain in a quiet part of Chicago in Illinois.
A fountain on a sunny day in Chicago.Foto: Mina.W / Shutterstock

Head to quieter neighborhoods in the Windy City.

The Loop—Chicago’s downtown business district—is home to top attractions such as Millennium Park, the Willis Tower, and the Art Institute, meaning that it’s reliably packed with visitors. Go beyond the Loop’s radius to see how locals live on a neighborhood tour, which tend to cover the heritage architecture of the Prairie District, street art in Pilsen, and the mansions of Wicker Park.

Discover local eateries

Deep dish pizza gets served up in Chicago in Illinois in a restaurant.
A slice of Chicago pizza gets dished up.Foto: Brent Hofacker / Shutterstock

Find the best of Chicago's food scene.

There’s more to Chicago’s food scene than deep-dish pizza. Enjoy shorter wait times and more diverse cuisine when you venture off-the-beaten-track. Food- and drink-themed neighborhood walks offer a first-hand introduction to many of the city’s less-trafficked culinary haunts, including the coffee shops of Logan Square, Chinatown, and the eateries of River North.

Visit year-round

Skates enjoy an ice rink in downtown Chicago in the winter.
Ice-skating in Chicago in winter.Foto: Brent Hofacker / Shutterstock

Head to the city outside the busiest seasons.

As well as soaring temperatures, summer in Chicago brings peak crowds. For a quieter experience of the city, visit during the shoulder season. Alongside the crisp breezes and golden leaves of fall, you’ll encounter quieter museums and sidewalks. And if you don’t mind a winter-wonderland experience, the Windy City’s snowfall provides a magical backdrop to your exploration.

Head underground

A navigation sign in the city of Chicago delineates the Pedway System in this part of Illinois.
A navigation sign in the city of Chicago.Foto: EQRoy / Shutterstock

Check out Chicago's subterranean Pedway.

One of Chicago’s most surprising attractions is the subterranean Pedway. Located beneath the Loop’s famed skyscrapers, the network lets you slip past crowds and discover a whole new side of the city. Book a guided tour to navigate the underground labyrinth with ease.

Take a private tour

A private boat tour takes place on the blue water of Chicago on a sunny day.
A boat takes a trip through Chicago.Foto: CK Foto / Shutterstock

Take the route of customizing your tour.

Private and small-group tours allow you to the explore the city in a more intimate setting. Soar over Chicago's iconic skyscrapers in a helicopter tour, or cruise along the lakefront on a private minibus tour customized for your group.

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