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14 North Side Chicago Hidden Gems


Experience the best the city has to offer.

Chicago might be the Windy City, but the wind never gets in the way of a good time — especially in the North Side. You can always expect lively nights listening to blues and jazz at classic clubs, explore your creative side at local art events, enjoy dining at Michelin-starred restaurants, and more. 

While all of those are great, some of the best options are a little harder to find. Locals know the best hidden gems throughout the city, and we’ve collected a few of the places you should try while you’re in town with a specific focus on the city’s iconic North Side.

From gorgeous, bustling neighborhoods like historic Lincoln Park, trendsetting River North, and vibrant Wicker Park, life in the North Side caters to those searching for the authentic experiences that Chicagoans love.

If you live here, your options for art, food, and music are endless, though some spots stand out from the rest. Whether you’re moving to the city or just heading over for a visit, you can discover these hidden gems that will give you a well-rounded experience you’ll always remember.

Music and dancing

Chicago’s music scene is legendary, and there are a few spots you should be sure to try. You can level up any date night or party at some of the city’s great venues and events.
  • Fizz Swing Dance
When was the last time you really danced? Prepare to buff your dancing shoes and head to Fizz Swing Dance, Chicago’s longest-running weekly social dance that’s a favorite among locals. Found at The Apartment in Lincoln Park, Fizz — as it’s known by Chicago swing dancers — offers a variety of lessons, community events, and a regular Monday night social to gather with friends or meet new people as you feel the music. Open to beginners and intermediate dancers, you can Lindy Hop, Charleston, East Coast Swing, and more — no partner or experience required. 
  • The Bassment
Travel through a secret door to the speakeasy-style cocktail lounge known as The Bassment. Beloved for its excellent drinks as much for its refined style, this one-of-a-kind nightlife experience is home to live blues and a local, laid-back atmosphere.

Dinner and Drinks

Restaurants and bars are plentiful in the vibrant North Side, which gives you plenty of options to try — but also enough that the choice can sometimes feel overwhelming. End the debates on where to grab your next dinner and try one of these local favorites we think you should be sure not to miss. 
  • Goose Island Fulton St. Taproom
Goose Island Fulton St. Taproom is one of the best spots for beer-lovers to visit in Chicago. They pride themselves on having what founder John Hall calls “damn fine beer.” Built in 1995, their brewery and bottling plant now produces 500 cases and 50 kegs in an hour. Since being acquired by Anheuser-Busch in 2011, Goose Island Beer Company can be enjoyed nationwide, but you can’t beat the experience of trying any of their 50 plus varieties of beers in their inviting taproom. 
  • Phodega
Soup is everyone's favorite, so Phodega is likely to please everyone from picky-eaters to adventurous connoisseurs. Although their menu is limited, you’ll find a high level of quality and care put into every meal served at this favorite cafe-market spot. 
  • The Rec Room
Great for private parties or a casual night out, The Rec Room is a house party-themed watering hole with a free jukebox. If you’re looking for a unique spot to host your next gathering or get a different experience from the average bar or club, it’s a great way to mix things up. Expect great drinks, 70s style decor, and tapas-style servings perfect for groups.
  • Hash
Hash is one of Chicago’s best brunch spots to bring along your friends or family. They’re committed to accommodating every allergy, diet, and food restriction. Nearly every dish can be made vegan, and there are several gluten-free options for guests to enjoy. Next to the hash, community involvement is what this restaurant prioritizes above everything. They partner with Chicago nonprofits, collectives, and grassroots organizations to help use their resources to help the community thrive.


One of the best ways to remember an incredible trip is by treating yourself to a souvenir. But whether you’re just visiting or are a Chicago resident already, you’ll quickly find there’s a great variety of shopping options available conveniently in the bustling North Side.
  • P.O.S.H.
Need new items for your luxury home or condo? For those interested in shopping for unique housewares, try P.O.S.H., a unique store that’s sourced from European flea markets and auction homes. Their vintage finds are unique and almost always too good to pass up. Located in the historic Tree Studio building in River North, this small shop is adored by many for its authentic assortment of silver, china, and dinnerware. Pro tip: If something in this store calls to you, don’t hesitate — it may not be there on your next visit.
  • Space Oddities 
Bookstore and gallery Space Oddities Chicago is home to incredible work by local artists and artisans. Their goal is to bring art, books, and stunning local goods straight to you — from ceramics, prints, and sculptures, to new and used books on poetry, art, and mythology. You can even schedule a personal tarot reading with the owner of Space Oddities, Sarah Luczko.


Everyone knows Chicago is a great city for art, but there’s plenty more to do than snap a picture with the world-famous Cloud Gate. Stroll through exciting museums, pick up some art at a local gallery, and get an inside look at the creative culture that helps the city thrive.
  • Dreambox Gallery + Studio
Dreamt up as a space for artists to connect with their community, Dreambox Gallery + Studio is an artist-run gallery, photography studio, and venue space that hosts an array of fascinating and creative events. It’s a great place to get a more personal look at the work of artists who are having an important impact on the city. In the summer, they also offer a gorgeous garden for visitors to explore. 
  • Museum of Contemporary Art Chicago
Though not the most hidden of the city’s gems, Chicago’s Museum of Contemporary Art has a vast, rotating collection of works from the 1920s onward that sets it apart from many other museums. Their exhibitions and featured works bring a unique character to the culture of Chicago, and the museum is known for its many great programs that help educate and involve the local community in the art scene. 
  • Addington Gallery
If you’re looking for a unique artistic experience, Addington Gallery is one of the North Side’s truly special galleries. It focuses primarily on mixed media works and those made with hot wax, which makes its collection of art for sale feel one-of-a-kind.
Spending time outdoors is a great way to take a relaxing break from the fast-paced excitement of the city’s shopping and nightlife. Though many know Chicago more for its arts and culture than its natural features, the city offers plenty of ways to get outside and enjoy the scenery. Local parks are perfect for walking, picnics, and fresh air, helping keep the whole family healthy and energized. 
  • Pulaski Park
Created by the West Park Commissioners in 1912, Pulaski (Casimer) Park hosts baseball and basketball fixtures, as well as a pool and gymnasiums. Families enjoy their special movie showings, holiday celebrations, and other evening events. 
  • Wooden Block Alley
In a small pocket of the city in Near North Side, you’ll find an unusual alley that draws a handful of visitors to get a closer look. Known as Wooden Block Alley, this small span of road is paved with square blocks of wood rather than stone, brick, or asphalt. It was created in 1909 and is one of only two wooden-paved roads in the city, which landed it on the National Register of Historic Places in 2002.
  • Jonquil Park
This small urban oasis is nestled into Chicago’s North Side. Jonquil Park includes play areas of various kinds, from an open grass field that’s great for sports to climbing areas, a splash zone for the summer months, and plenty more to keep the whole family entertained right in the heart of bustling Lincoln Park.

Experience the North Side magic

If you’re interested in the vibrant lifestyle of the North Side, Tom Bakritzes is an expert guide who can help you navigate the world of North Side Chicago luxury homes. Get in touch today to discover gorgeous Lincoln Park homes for sale and other North Side real estate.

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