Neighborhood Guide: Chicago

Planning a trip to the Windy City? Learn about the best local attractions and activities with our guide to Chicago neighborhoods. From raucous Wrigleyville to the sophisticated vibe of the Gold Coast, Chicago has something for everyone.

The Loop

Chicago’s official downtown area, The Loop, is famous for its striking architecture, world-renowned restaurants and incredible cultural institutions. The business of the world is conducted inside many of those towering skyscrapers, while locals and tourists flock to Grant Park and Millennium Park for outdoor fun. You can even reenact most of “Ferris Bueller’s Day Off” with a day (or two) of exploration around The Loop. Don’t miss:

• "The Ledge" at the top of Willis Tower (Formerly the Sears Tower)
• Buckingham Fountain at Grant Park
• A riverboat cruise on the Chicago River
• Giordano's PIzza, for a taste of the legendary Chicago deep-dish pizza
• Millennium Park's "Cloud Gate," aka "The Bean," now known as a true Chicago icon
• Chicago Cultural Center, a beloved performance venue
• Art Institute of Chicago, considered one of the world's best museums

Wrigleyville

Nestled in the shadow of the second-oldest baseball stadium in the country, Wrigleyville is a beloved Chicago neighborhood for barhopping sports fans and young professionals alike. Here, live music and sketch-comedy performance venues blend with casual eateries and souvenir shops to keep virtually everybody busy—and in the best of spirits. Tour the “friendly confines” of Wrigley Field, for a player’s view of the ballpark. Take a pub-crawl along Clark Street (as well as Addison and Sheffield Avenue). Also, if you plan it right, you might be able to take in a show at the Metro Chicago, a venue for headliner performances.

Wicker Park

Wicker Park is a Chicago neighborhood that has transformed several times over the past two centuries. It was once home to Northern European immigrants and many wealthy merchants and brewers. Today, it’s a Midwestern hub for the edgy, artsy and hip. In fact, in 2012, Forbes magazine named it “The #4 hippest hipster neighborhood in the country.” One of the most convenient ways to get a feel for the esoteric boutiques, art scene and current craft cocktail craze is at the Flatiron Arts Building. Check out the historic Chopin Theatre for fabulous live performances, too. And don’t forget to pay your respects to 19th century developer Charles Wicker at the park that bears his name—Wicker Park.

Lincoln Park

The North Side Chicago neighborhood of Lincoln Park is a diverse residential and business corridor that also features some of the city’s best entertainment and cultural venues. At its heart is its namesake park, a sprawling 1,200 acres of green space along Lake Michigan where admission to Lincoln Park Zoo is always free and the Lincoln Park Conservatory offers a tropical paradise escape—even on a blustery winter day. You’ll also enjoy the Chicago History Museum here. When the weather’s good, hit the North Avenue Beach for sun and fun. You’ll soon agree that Lincoln Park is a tangible reminder of Chicago’s motto, “urbs in horto”—“City in a Garden.”

Gold Coast

Just north of downtown is the Gold Coast. One of the country’s most affluent neighborhoods, it’s packed with historic mansions, internationally famous designer boutiques along Oak Street and Michelin-starred eateries. As you walk, shop, eat and ogle, make sure to stop into the Museum of Contemporary Art Chicago. Then, for something completely out of the ordinary, don’t miss the quirky International Museum of Surgical Sciences.

Ready to travel? Find hotels in Chicago.