Cool Neighborhoods in Chicago for Visitors to Experience the City

What are the cool neighborhoods in Chicago? Windy City residents could argue for hours on this subject. It really depends on your interests and what type of person you are.

Some folks will prefer the hipster neighborhoods with lots of nightlife, while others want more quiet, residential parts of town.

Each Chicago neighborhood features its own distinct vibe and ethnic heritage. There are far too many cool neighborhoods in Chicago to list them all here.

For example, we’ve left out Greektown, Lincoln Park, Edgewater, Ukrainian Village, Chinatown, River North, Bridgeport, and Lakeview. All of those are pretty awesome places too, so be sure to venture out beyond the ones on my short list!

When you’re ready to visit the Windy City, book your flight, search for a place to stay in Chicago, and check out these cool neighborhoods after you arrive.

Cool Neighborhoods in Chicago: My List

Here’s one person’s list. Feel free to leave a comment with your suggestions!


pilsen - best cool neighborhoods in Chicago
Pilsen is definitely one of the cool neighborhoods in Chicago.

Once a busy Czech neighborhood, Pilsen grew into one of the most prominent areas of Chicago and boasts a strong Latin influence.

You’ll find colorful street art all over the neighborhood, along with authentic Mexican restaurants and other local shops. Check out the National Museum of Mexican Art, a free attraction that offers some of the most interesting art pieces in the city.

Wicker Park

For a few decades, Wicker Park has been one of the hottest spots in Chicago, with nightclubs, live music venues, and bars open until late at night.

Wicker Park highlights include Double Door, an iconic concert club; Reckless Records, a longtime independent music store with a large selection of vinyl; and Myopic, an indie store with several floors of used and new books.

Update: Double Door closed a couple years back, but is in the process of relocating to Uptown.

The Loop

The center of downtown is known as the Loop. That’s where you’ll find many of the Windy City’s top tourist attractions, like the Willis Tower, Millennium Park and its famous Cloud Gate sculpture (the “Bean”), and the Art Institute.

Hop on the architecture boat tour, one of the coolest things to do in the whole city!

The Loop is where the Lollapalooza music festival takes places every summer. You can find iconic Chicago food staples here, too, such as deep-dish pizza restaurants and hot dog stands.

Getting around the Loop is easy — just hop on the “L” train line.

Hyde Park

The vibrant South Side community of Hyde Park is where President Obama lived before running for the nation’s highest office. It’s also the home of the Museum of Science and Industry and the DuSable Museum of African American History.

The center of neighborhood life is the University of Chicago and its surrounding streets, which offer activities and businesses that cater to the student-age crowd, so you know there’s always something exciting going on.


Fifteen miles north of Hyde Park (have we mentioned what a huge city Chicago is?) lies Andersonville, an area that was originally inhabited, in the late 1800s, by Swedish immigrants.

Today, the neighborhood features excellent shopping and high-quality restaurants with sidewalk seating, as well as the nod to the past that is the Swedish American Museum.

Andersonville boasts one of the most popular street festivals in the city in Midsommarfest, which takes over North Clark Street in June.

lady gregorys restaurant - chicago andersonville neighborhood

They also have some great restaurants here, like Lady Gregory’s Irish Pub. Get the chicken pot pie (pictured above!)

Logan Square

As Wicker Park became too expensive and too popular for the hipsters, many moved north to Logan Square, which has now revitalized itself.

Check out attractions like the renovated Logan Theatre, which plays second-run movies at a discount; restaurants like the farm-to-table Lula Cafe and the vegan Chicago Diner; and bars like Revolution Brewing and Slippery Slope that fall somewhere between divey and trendy.

Don’t miss the large farmers’ market on Sunday on Logan Boulevard. Logan Square is one of my favorite neighborhoods in Chicago, which is why I lived there for several years!

Moving Beyond These Neighborhoods

Elsewhere in Chicago, consider checking out the Garfield Park Conservatory in Garfield Park, the Green Mill jazz club in Uptown, the Tribune Tower in River North, and Chicago comedy and improv in various neighborhoods.

Regardless of your interests, you’ll find something fun to do in each of these iconic Chicago neighborhoods. And consider also taking a road trip from Chicago to somewhere else in the Midwest.

And check out this list of fun winter activities in Chicago, and things to do in Chicago at night!

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