What makes a neighborhood cool? Is it the bars and restaurants? The shopping? The architecture? The outdoor space? In Chicago, the answer is a little bit of everything. This Midwestern city’s neighborhoods are full of foodie magnets, nightlife, boutiques, beautiful homes, and parks. Although it’s hard to single out just a few, here are five cool neighborhoods in Chicago to explore.

Boystown

Boystown Chicago

Boystown is known for its LGBTQ pride. Each summer, the neighborhood hosts Pride Fest and Parade. But in Boystown, the party rarely ever stops. A pocket neighborhood of Lakeview, Boystown has bars lined up and down Halsted Street and North Broadway. For cocktails and unbeatable entertainment, the drinks and divas of Kit Kat Lounge & Supper Club are a popular neighborhood experience.

Spots to Check Out:
  • Center on Halsted: The neighborhood’s LGBTQ community center offers a wide range of programs, events, and support.
  • Chicago Diner: This restaurant is a staple for any Chicagoan who embraces vegetarianism. The milkshakes, completely vegan, are well worth the trip regardless of your diet.
  • Pingpong: Fresh Asian fusion dishes and cocktails inspired by 1930s Shanghai are the trademark of this Boystown restaurant.

Hyde Park

Hyde Park
Hyde Park Chicago

Hyde Park is made picturesque by the University of Chicago Campus and striking architecture, including Frank Lloyd Wright’s Frederick C. Robie House. Once a suburb, the South Side neighborhood feels more spacious than many of its counterparts.

This feeling only intensifies as you move eastward. The neighborhood borders the lake and includes a huge chunk of park space, Burnham Park, which features Promontory Point. Right on the lake, this feature has a spectacular view of Chicago’s skyline. Hyde Park is also home to one of the city’s most recognizable cultural touchstones: the Museum of Science and Industry.

Spot to Check Out:
  • Jackson Bark: Jackson Bark is not your average dog park. Here, dogs are treated to pools, obstacles, and toys.
  • The Promontory: The low-lit restaurant, bar, and music venue features a big menu of-the-moment cocktails—think spritzes, frose, and mezcal drinks— that embodies Hyde Park’s hipness.
  • Smart Museum of Art: The Museum of Science and Industry is not Hyde Park’s only cultural institution. The Smart Museum of Art features a rotating and eclectic blend of exhibitions.

Logan Square

Logan Square
Logan Square Chicago

Logan Square is another Chicago neighborhood that prides itself on lively nightlife. The neighborhood is packed with restaurants ranging in cuisine and style and bars that keep patrons out until daybreak. Those who take their libations seriously will appreciate the neighborhood distillery (Chicago Distilling Company) and brewpub (Revolution Brewing) on Milwaukee Avenue. For more fun and games, Logan Arcade serves drinks with arcade games.

Spots to Check Out:
  • The Pink Squirrel: Logan Square has stiff competition when it comes to bars, so naturally the watering holes like to come up with a unique twist. In this case, try out retro cocktails with mini bowling lanes.
  • Passion House: Among the neighborhood’s multitude of coffee shops, Passion House stands out with creative lattes and a sunny, colorful interior.
  • Chiya Chai: If tea is more your drink of choice, Chiya Chai’s extensive menu of chai teas pair well with its savory dishes that incorporate Nepali and Indian flavors.

Pilsen

18th St L-Trail Pilsen / Photo by Adam Jones / CC BY-SA

This Lower West Side neighborhood is about as cool as a neighborhood can get. It’s known for its eye-catching murals, authentic Mexican food, and nightlife. Deciding on the best taco in Pilsen may just be impossible with spots like Los Comales, La Vaca, 5 Rabanitos, and a whole lot more. Plus, three record shops within walking distance of one another makes Pilsen a hotspot for vinyl collectors.

Spots to Check Out:
  • Thalia Hall: Concertgoers are drawn to the live shows put on by this historic music venue.
  • Simone’s: Simone’s is a classic neighborhood bar with a solid menu of food and drinks. The bar is cozy in the cold months, but crowds spill out onto the patio in the summer.
  • Open Books: The nonprofit Open Books supports literacy, and it is heaven for anyone who loves exploring the stacks of a used book store.

Ravenswood

Ravenswood
Ravenswood / Photo by Andrew Jameson / CC BY-SA

Much like Hyde Park, Ravenswood feels pretty removed from the density and rush of neighborhoods closer to downtown. Instead, this North Side neighborhood feels like a place for afternoon drinks on a Saturday or Sunday brunch—try Over Easy Cafe or Cafe Selmarie. Ravenswood’s Malt Row fits seven breweries and distilleries into 1.5 miles. Sample local beers and spirits and tour some of the facilities that make them. 

Spots to Check Out:
  • Old Town School of Folk Music: Whether you are into listening to music or making it, this Ravenswood spot is a welcome neighborhood favorite. The Old Town School of Music holds classes for kids and adults, as well as concerts.
  • Merz Apothecary: Merz Apothecary, dating back to the 1800s, is an old-school drugstore with an enormous selection of health and wellness products.
  • Groundswell Coffee Roasters: Open 12 hours a day, Groundswell on Damen Avenue serves residents’ caffeine cravings before, during, and after work.