How to Get Off the Beaten Path in Chicago

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.

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.

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.

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.

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.

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.