Chicago’s Most Popular Neighborhoods: Where to Go & What to Do

Chicago’s Most Popular Neighborhoods: Where to Go & What to Do

Welcome to Chicago, my favorite city! Where every neighborhood offers deep-dish pizza and a never-ending stream of things to do. From trendy hotspots that will spice up your social media page to iconic tourist attractions that will make you feel like a history buff, there is truly something to do around every corner. However, there are a few must-sees that you don’t want to pass up in each area.

The guide below will help you get the most out of Chicago’s most popular neighborhoods. Whether you’re craving a craft cocktail, a shopping adventure, or a dose of nature, we’ve got you covered. We’ve divided the guide up by neighborhood and included popular attractions—along with a few hidden gems!

Gold Coast

Gourmet restaurants, high-end shopping boutiques, and spa retreats are just a few of the finer things you will find in this classy, lakeside neighborhood. Gold Coast apartments are known to be the epitome of luxury living, and this area as a whole is no different—it is dripping in indulgence. 

Washington Square Park 

This registered historic landmark is stunning and tranquil. With its Victorian fountain, large trees, and gorgeous landscaping, it is no wonder that locals go to this park to escape the bustle of the city. In this park you can also find the historic Newberry Library, which is open to the public. 

Old Chicago Water Tower

Located on The Magnificent Mile, this water tower boasts brilliant architecture with its detailed limestone build. It is the second oldest water tower in the US and home to a free gallery that hosts exhibits by local artists. Looking for a bit of shopping? Check out one of Chicago’s largest shopping malls across the street, Water Tower Place.


You don’t want to overlook this vegan restaurant, which offers fresh and flavorful snacks and superfoods. Ingrained is perfect for any time of day, from a pick me up in the morning to sweet tooth satisfier at night. (HIDDEN GEM) 

River North

Views of the Chicago River and Lake Michigan are enough to bring people to this area, but it offers more than just breathtaking scenery. River North is home to the second-largest concentration of art galleries in the US. Plus, its nightlife is booming thanks to a vast selection of bars and some of the best cuisine found in all of Chicago.

Cocktails in River North


Formerly known as The Merchandise Mart, this massive building with its own zip code is sure to keep you entertained. It is the largest commercial building in the world and offers everything from shopping to cooking classes.

The Gallery District

Chicago, Superior and Huron streets between Lasalle and Orleans is the place to go to get your fill of art. Only Manhattan beats out this area as far as the highest concentration of galleries goes!

Chicago Riverwalk

Take a stroll along this historic walkway that lines the Chicago River for 1.25 miles. At any time of day, you will get an eyeful of some of the most stunning, historic architecture that the city has to offer along the Chicago Riverwalk. However, sunrise and sunset offer an exceptionally picturesque view.


Old town charm found right in the big city! This area is a must for those that crave a slower exploration that involves quaint cafes, antique shops, and reading nooks. It is the perfect Chicago neighborhood to grab lunch and go shopping for the day.

The Neo-Futurist Theatre

Audience participation is half the fun of the theatre productions at this venue. These interactive performances at affordable prices are a must if you are in the area.

Andersonville Farmers Market

Hit up this farmers market for everything from artisanal sweet treats to local produce. It is a great way to support the community while indulging in some of the freshest food Chicago has to offer.

Puppet Bike

This street performer is a bit of a Chicago icon at this point with his mobile puppet theatre that can commonly be seen in Andersonville and other downtown areas. If you are lucky enough to stumble upon the miniature theatre towed around by performer Michael King, don’t pass up the opportunity to catch a show. (HIDDEN GEM)

The Loop

If you love to be in the center of the action, The Loop is for you! This central hub is overflowing with culture thanks to an abundance of museums, sculptures, and landmarks in the area. Nature lovers are also no stranger to this downtown neighborhood with the many walking trails and parks that it offers. Plenty of great places to enjoy a book or eat lunch outside.

“The Bean”

Whether you love art or are looking for a giant mirror, The Bean is the place to go. Alright, it may technically be called Cloud Gate, but the abstract art installation is known to locals as The Bean. It is located in Millennium Park and quite the sight with its large stature and high shine finish that resembles liquid mercury.

Maggie Daley Park

This ice skating ribbon that resembles a snake with its curvy path is the place to be in the winter. You can either bring your own skates or rent some right there.

Chicago Architecture River Cruise

All aboard! This highly-sought-after attraction gives you views of the marvelous architecture that the city is known for. The Chicago Architecture River Cruise also offers a detailed narrative of the sites you float by, a snack bar, and a cocktail bar.

Wicker Park

Originally a popular district for merchants in the 19th century, it is no wonder that this area still harbors a thriving creative community. An abundance of one-of-a-kind shops and galleries that sell and display makers’ wares are housed in this neighbourhood—making it a fantastic place to find unique gifts! In Wicker Park, you can also find some of the best cuisine in the city.

Flat Iron Arts Building

You can’t go wrong with starting a day of exploration in this area. First, there is the Flat Iron Art Building, which is home to an array of galleries of different disciplines. Then just a short walk away, you can find world-class restaurants for quick lunch as well as an assortment of boutiques. 

The 606 Trail

Previously an elevated railroad, these unused routes have been transformed into trails where you can walk, run, or bike. No matter which type of exercise you choose, though, The 606 will treat you to a stunning view of Wicker Park and the surrounding neighborhoods. 

Gold Star Bar

This friendly neighborhood bar has a homey feel with its attentive staff, jukebox, and wide span of ages. It doesn’t have any gimmicks or bells and whistles, but it does offer great drinks at reasonable prices! (HIDDEN GEM)

No matter which neighborhood you are exploring, don’t forget to talk to the locals. Hitting up some of the most popular attractions is always great (they’re favorites for a reason!). But locals can guide you to spots off the beaten path, helping you experience the area to its fullest. And people in Chicago are so nice.

This is a sponsored post.

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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