Wicker Park is well known as the city’s premier hipster haven, thanks to its copious vintage boutiques, vegetarian restaurants, and artisanal donut shops. Stroll the tree-lined streets, check out some shops, then grab a seat at Big Star to eat tacos on what is arguably one of the city’s best patios.
A few blocks northwest of Wicker Park sits Logan Square – its relaxed, less-gentrified cousin. The neighborhood is a magnet for artsy types as well as up-and-coming chefs looking to make a name for themselves, making it one of the best places to find out what’s next on the food scene. It’s also home to some of the city’s best cocktail bars (like the gin-centric Scofflaw) and brunch spots perfect for the morning after.
Street art, the best Mexican food in the Midwest, and Thalia Hall (one of Chicago’s hottest destinations for live music) – there are a lot of reasons to visit Pilsen. Don’t leave here without a stop at the National Museum of Mexican Art, the largest Mexican cultural center in the nation.
With the highest concentration of buzzed-about restaurants in the city, the West Loop is like a restaurant Hall of Fame. Stroll down Randolph Street to see eateries from Chicago food scene heavy-hitters like Paul Kahan and Stephanie Izard. Just make sure to book reservations ahead of time to avoid disappointment.
Once an entertainment destination that helped to usher in the silent film era (Charlie Chaplin used to produce films here at the now-defunct Essanay Studios) and the jazz age, Uptown is a vibrant blend of old and new Chicago. Head here for some of the best Vietnamese food in the city, or explore the Art Deco architecture and restored movie palaces. Check out a show at the Riviera or Aragon Ballroom—both dating back until at least the 1920s—or grab a drink and listen to some jazz at the iconic Green Mill, once a haunt of gangster Al Capone.
While Chicago’s Chinatown may be smaller than New York’s or San Francisco’s, it’s still easy to lose yourself for a day here. Stroll down Wentworth Avenue to peruse dim sum options, stand in the shadow of the Chinatown Gate, or head to Chinatown Square (the largest Chinese mall in the Midwest) to shop at stores like Aji Ichiban, an impressive Asian candy and snack store. Pro tip: skip the L and grab a water taxi from the Loop, which travels down the south branch of the Chicago River to scenic Ping Tom Memorial Park.
Traditionally a working-class neighborhood, Bridgeport is undergoing a revitalization thanks to an influx of restaurants, bars, and bakeries. Maria’s Packaged Goods—a bar and liquor store rolled into one—has been singled out as one of the best bars in the nation thanks in part to its extensive craft beer list. For a drink with a dose of history visit Chicago’s longest-operating tavern, Schaller’s Pump. The neighborhood is also known for its burgeoning art scene, thanks to spots like Zhou B Art Center and the Co-Prosperity Sphere.
Situated on the South Side of Chicago, Hyde Park is a cultural jewel box. Visit the scenic University of Chicago campus (known for its numerous Nobel Prize-awarded alumni), the Museum of Science and Industry (the largest science museum in the Western Hemisphere and the only original building still standing from the 1893 World’s Fair), Frank Lloyd Wright’s Robie House (considered one of the most iconic buildings in American architecture), and the home of former President Barack Obama.
One of the most vibrant LGBT neighborhoods in the world, Boystown is the home of Center on Halsted, a theater/recreation hall/community center for Chicago’s gay community. The neighborhood is also a destination for gay bars, dance clubs, theaters, and comedy clubs.
Once the center for Chicago’s Ukrainian community, this pocket-sized neighborhood just southwest of Wicker Park is populated with dive bars, vintage boutiques, old Ukrainian delis, and cafés perfect for a leisurely brunch. The neighborhood is also home to the Empty Bottle, a hole-in-the-wall music venue known for live alternative music.