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How to Get Off the Beaten Path in Chicago

Get to grips with a new side of Chicago, beyond the "Bean."

A couple walks along a Chicago thoroughfare in Illinois
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.

Many well-known Chicago landmarks are celebrated the world over, from the Willis Tower and Millennium Park to the Art Institute. But there’s more to the Windy City than meets the eye. Step off the beaten path, and see a side of the city that many visitors miss at these unconventional Chicago attractions.

Pay a visit to the Prairie District

Prairie District in the heart of downtown Chicago.
The Prairie District is in the middle of downtown Chicago.Foto: Henryk Sadura / Shutterstock

Explore this Near South Side neighborhood.

A quick trip from the architectural behemoths and cultural heavyweights of the Loop, you find the Prairie District: a petite neighborhood in the Near South Side with its own history and landmarks. Occupied by elite Chicagoans at the turn of the 20th century, the area—also known as the Prairie Avenue District — now boasts the Clarke House Museum (the city's oldest surviving house), John J. Glessner House, and more. Take a walking tour to explore up close.

Visit the American Writers Museum

The art deco exterior of American Writers Museum on Michigan Ave in Chicago.
The American Writers Museum on Michigan Avenue.Foto: Pamela Brick / Shutterstock

Get inspired by these literary greats.

Established in 2017, the American Writers Museum is one of Chicago’s newer institutions. It provides a much less crowded experience than at better-known spots such as the Field Museum of Natural History or the Art Institute of Chicago. The museum celebrates literary cultures and offers interactive exhibitions designed to fire up your creativity, whether you’re an avid reader or aspiring novelist. Prebook tickets in advance for seamless sightseeing.

Escape the crowds at The 606

The 606 park, also known as the Bloomingdale Trail, with runners enjoying it in Chicago.
An elevated park in Chicago, also known as the Bloomingdale Trail.Foto: Thomas Barrat / Shutterstock

Discover Chicago's answer to New York’s High Line.

Beyond the bustle of Millennium Park or Grant Park, Chicago has other less trafficked green spaces that provide urban escapes. One such option is The 606, often described as the Windy City’s answer to New York’s High Line as it's a public park located on a disused, elevated train track. Opened in 2015, the park is outfitted with art installations, greenery, and walking and biking trails. Explore it on a walking tour to see its highlights.

Take a tour of Pilsen

Horseback riders in Pilsen in Chicago on Mexican Independence Day.
The Pilsen Mexican Independence Day Parade.Foto: Roberto Galan / Shutterstock

Learn more about the city's Mexican heritage.

Chicago is known for its characterful neighborhoods, each of which has its own, unique personality. Venture beyond the Loop, and see how real Chicagoans live on a walking and cultural tour of the eclectic and dynamic Pilsen area. Home to beautiful murals and street art, the National Museum of Mexican Art, and a range of destination-worthy restaurants and cafes, the neighborhood offers a slice of local life.

Explore the Driehaus Museum

Outside the Richard Driehaus Museum in downtown Chicago on a sunny day.
The Richard Driehaus Museum in downtown Chicago.Foto: Thomas Barrat / Shutterstock

Enjoy the artwork at this restored mansion.

One of Chicago’s most distinctive museums, the Driehaus is a treasure trove of decorative arts pieces. The small museum, housed in the restored Nickerson Mansion, offers a glimpse into the Windy City’s Gilded Age splendors and excesses. Book your tickets before you travel, and explore at your own pace.

Go sightseeing in Naperville

Shops and restaurants in red-brick buildings along the Naperville Riverwalk in Chicago.
Shops and restaurants along the Naperville Riverwalk.Foto: James Andrews1 / Shutterstock

A top spot for foodies in Chicago.

A Chicago suburb—and a thriving mini city in its own right—Naperville serves up plenty of charm, plus historical landmarks and family-run restaurants to boot. Stroll the pretty Naperville Riverwalk on a scavenger hunt, admire the soaring Moser Tower, and visit the city’s many eateries, from brewpubs to traditional pizzerias.

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