With a rich cultural history, shoreline vistas and attractions, and sought-after homes and condominiums, it’s no wonder that Uptown is one of Chicago’s most coveted real estate hotspots. Right on the Lake Michigan shore, it offers anything from landmark mansions and vintage apartments right up to modern lofts and chic renovated houses. Step out the door of your new home, and you’ll find plenty of upscale restaurants and shopping opportunities, plus a host of the city’s best nightlife venues.

Recent History

Uptown remains a popular tourist destination thanks to its Entertainment District, with new shops and restaurants opening their doors each year and ties to prohibition-era culture. In fact, Uptown Square was recently designated as a National Historic District on the National Register of Historic Places. It’s also become home to one of Chicago’s best-loved festivals – the Windy City RibFest. Celebrating summer food over three glorious days with live music throughout, arts and crafts for kids, and beer and wine for the adults, it’s an event that residents are always sure to mark on their calendars.


Uptown is a great place to hit the streets, with a diverse range of places to pick up a bite, enjoy a drink, or shop to your heart’s content.

One of the area’s most celebrated stores is Foursided; though it begun by simply offering custom frames and greeting cards, it has evolved into the ultimate home-design general store, with enough prints, art, and reproductions to fill your Uptown home with character. Shoppers also rave about Milk Handmade, which was voted as 2012’s “Best New Boutique” in Time Out Chicago’s annual Shopping Awards and offers a stunning selection of handmade women’s clothing and accessories. Bookworms will want to head straight to Shake Rattle and Read Book Box. Aside from shelf after shelf of second-hand volumes, it offers vinyl, DVDs, CDs, old magazines, and rare comic books.

The culinary scene is just as impressive. If you’re in the mood for comfort food, head to The Reservoir — you’ll be able to chow down on lamb burgers and cheese fries while perusing a truly impressive beer list of cocktail menu. You can also give Carmela’s Taqueria a try for some delicious tacos, or take a trip to Loving Heart for mouth-watering vegan fare.

When you’re done with dinner, try the Green Mill Cocktail Longue; once a favored spot of Al Capone, this former speakeasy now hosts the Uptown Poetry Slam and features live jazz. For a more modern evening, try Michael’s Pizzeria & Sports Pub. Often claimed to produce the best pizza in town, it’s also the perfect place to kick back and watch the game.

Aside from its restaurants, bars, and shops, Uptown is home to a wide range of schools, including:

A Day in the Life

A day in the life of an Uptown resident usually starts with a stroll along the park and beach system extending along Lake Michigan. Alongside its numerous biking and jogging paths, you’ll find volleyball courts in the summer and sledding hills during the frosty winter months. If the sun is shining bright, Montrose Beach is the perfect place to spend the morning, whether you’re swimming, sunbathing, or renting a kayak.

You can even finish your morning swim by picking up a snack at The Dock at Montrose Beach. Alternatively, try taking brunch at Inspiration Kitchens. It’s staffed by graduates of an award-winning kitchen services program, and provides some of the best eggs benedict and French toast around. For something a little more filling, head to Argyle Street. Commonly referred to as Little Saigon or New Chinatown, it’s a world unto itself. You’ll find delicious Asian delicacies at any one of its restaurants.

Once the sun has set, there’s no reason to head to home. Instead, book a show at the notorious Annoyance Theatre, which is committed to pushing the boundaries of comedy with their hilarious absurdist humor. If live music is more your scene, there’s no better place than The Aragon Ballroom. It played host to the nation’s best-known jazz groups during the 1920s and 1930s, and his since welcomed such storied greats as Frank Sinatra, The Rolling Stones, and Nirvana.


Uptown is bordered by W. Foster to the north, Lake Michigan to the east, W. Irving Park to the south, and Clark to the west. There’s easy access to the expressway, but the area also benefits from Chicago’s public transportation system. The CTA Red and Purple lines stop at Argyle, Lawrence, Wilson and Sheridan, and buses cover most major streets.

Find Uptown Real Estate With Chicago Home Partner

Chicago Home Partner boasts the experience necessary to help you find your own place to call home in Uptown, whether that means finding a house, condominium, or rental property. Contact one of our team members today to begin your search for Uptown real estate.

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