8 Must-See Chicago Neighborhoods and How to Visit

The perfect place to start any Chicago tour, the Loop (so named for the shape of its elevated train tracks) is a key part of the city’s Downtown, and home to many of its best-known landmarks and historical icons, including the Willis Tower, the Chicago Riverwalk, Millennium Park (and its famous “Bean” sculpture) and the Buckingham Fountain. And that’s before you get to its cultural highlights, which range from the Art Institute of Chicago to the Chicago Theatre. Architectural walking (and river cruise) tours, Chicago day-trip itineraries, and food-centric excursions are all ideal ways to discover the Loop’s myriad charms.

Though Chicago’s Chinatown was itself located in the Loop in the 19th century, it later moved to an area just south, along Cermak Road and Wentworth Avenue. With the arrival of the Chinatown Square development in the 1990s, the neighborhood expanded further; today, fed by a steady stream of international college students, it has become a cultural hotbed (and a major destination for visiting foodies). Fittingly, a culinary-themed walking tour is a great way to explore Chinatown’s top restaurants and connect with locals, all while learning about the neighborhood’s history.

Distinguished by the DuSable Black History Museum and Education Center, the top-ranked University of Chicago, and President Barack Obama’s former home (and future presidential library), Hyde Park is one erudite locale, and one of the city’s unmissable cultural and historical hubs. The neighborhood can be explored as part of an African-American heritage tour, as well as a tour spotlighting the must-see areas of Chicago’s South Side.

Just west of Lincoln Park, whose highlights include the Lincoln Park Zoo and Lincoln Park Conservatory, this North Side neighborhood is known for being well-heeled and picturesque today—though its notorious 1920s chapter also lands it on the city’s Al Capone and gangster-themed tours. For a more salubrious experience of Lincoln Park, you can see it as part of a full-day tour of Chicago’s different neighborhoods (or reserve, way in advance, a table at the Michelin-starred Alinea, regularly named one of the world’s best restaurants).

Just across the river from the thrum and energy of the Loop, River North offers a similar range of attractions, including major architectural highlights, soaring skyscrapers, and popular tourist attractions, with a particular artistic and culinary focus. Home to hundreds of art galleries and the shopping destination that is the Merchandise Mart—and bordering the Magnificent Mile, one of Chicago’s preeminent retail districts—this neighborhood is an ideal accompaniment to your Downtown excursions. Embark on a food-themed walking tour to taste a range of Chicago specialties, all while learning about River North’s history and culture.

Wondering where Chicagoans go to let loose, grab a bite, or meet friends for drinks? Wicker Park, part of the broader West Town area, has long been known for its hip bars, cafes, and boutiques. On a guided food tour, you’ll also spot its architectural and historical highlights, while a biking tour makes it easy to taste the best of the area while soaking up its unique ambiance. Or, for a specialized experience, go for a pizza crawl of Wicker Park (as well as the equally appealing neighborhood of Bucktown, right next door).

Part of Chicago’s Lower West Side, the vibrant neighborhood of Pilsen is home to a thriving Latino community. Opportunities for cultural exploration abound, from enjoying a private tour of the neighborhood’s murals and street art to visiting the National Museum of Mexican Art (home to works by artists such as David Alfaro Siqueiros and Diego Rivera). Pilsen is also an exceptional place to eat—come hungry, so you can stop for bites at the taquerias, Mexican bakeries, and birria specialists that call the neighborhood home.

The name of this locale isn’t overstated. Poised right on the sandy sweep of Lake Michigan within Chicago’s Near North Side, this most gilded of areas has long been a destination for the city’s rich and famous. For visitors, its impeccable lakefront vistas are matched by its architectural gems—head to the Astor Street District to admire the sights, and seek out the Charnley-Persky House (co-designed by Frank Lloyd Wright). Whether on a self-guided audio walking tour or a zippy bike tour along the lake, you can get a feel for its well-heeled ambiance.