OLD TOWN

Old Town is one of Chicago’s most iconic neighborhoods, offering a mix of history, culture, and vibrant city living. Old Town exudes charm with its historic Victorian architecture, including St. Michael’s Church, one of the few structures to survive the Great Chicago Fire. As the birthplace of modern improv, it’s home to The Second City, where many comedy legends started.

What To Expect

Expect a neighborhood where cobblestone charm meets urban hustle. Old Town brings vintage buildings, loud laughter from comedy clubs, and locals who genuinely love where they live.

The Lifestyle

Old Town’s lifestyle blends sidewalk cafés, artsy festivals, and dive bars with deep roots. It’s both chill and charged, with a touch of chaos if you want it.

Local To-Do's

Catch a show at The Second City, grab ribs at Twin Anchors, browse boutiques on Wells Street, or stumble into a festival that shuts down the block.

Old Town’s origins date back to the 19th century, when it was a trading hub for Native American tribes. By the 1940s, it had shifted to an urban neighborhood, developing into the Old Town Triangle. The success of the Old Town Holiday Festival cemented its identity, and the name Old Town stuck.

Today, it thrives as a dynamic, urban hub filled with eclectic shops, acclaimed restaurants, vibrant nightlife, and rich cultural landmarks. Old Town remains a neighborhood where history and creativity blend seamlessly.

Listings in Old Town Chicago We Think You'll Love

Things To Do & Explore In Old Town Chicago

Old Town isn’t for the bored or bland. Walk its historic streets, where comedy legends cut their teeth at The Second City, and bold murals pop from brownstone walls. Stop by Zanies Comedy Club or Old Town Ale House for some unfiltered laughs and late-night drinks.

When the sun’s out, the whole neighborhood feels like a block party. The Old Town Art Fair and Wells Street Art Festival bring music, food, and original artwork right to your doorstep. You can stroll, snack, sip, and still feel like a local.

Nightlife and Entertainment

Old Town doesn’t just have nightlife. It helped invent it. THE SECOND CITY is the comedy institution where stars like Tina Fey and Steve Carell cut their teeth. Zanies Comedy Club keeps the laughs rolling with bold stand-up acts, while OLD TOWN ALE HOUSE serves stiff drinks with even stiffer opinions painted on its walls. And TWIN ANCHORS? If it was good enough for Sinatra, it’s probably good enough for you.

Annual Events

If you’re bored in Old Town, that’s on you. The OLD TOWN ART FAIR brings fine art, live music, and gourmet street eats into the neighborhood every summer. No ticket required. Just good taste. Then there’s the WELLS STREET ART FESTIVAL, where artists, performers, and food vendors turn the entire street into a full-blown cultural flex.

Dining and Local Eats

Old Town eats like a pro. ORSO’S RESTAURANT brings candlelit Italian romance without the stuffy vibe. TOPO GIGIO delivers bold pasta in a relaxed setting. GAVROCHE feels like a Parisian escape without the airfare. And then there’s PROFESSOR PIZZA, throwing down some of the best pies in the city. No apology needed.

Education and Schools

Don’t let the nightlife fool you. Old Town knows how to raise smart kids. Abraham Lincoln Elementary delivers strong academics and even a Virtual Calm Room to support student wellness. LaSalle Language Academy goes further with immersive programs in Mandarin, French, Spanish, and Italian. The kids here don’t just learn. They grow up worldly.

Share This With a Real Estate Savvy Friend

Why People Choose Old Town

Old Town’s unique blend of historic charm and urban energy makes it one of Chicago’s most desirable neighborhoods. Its mix of quiet, tree-lined residential streets and vibrant commercial areas offers the best of both worlds. Whether you’re drawn to its comedy scene, top-notch dining, or charming boutiques, Old Town has something for everyone. Its proximity to Lake Michigan and downtown Chicago makes it even more appealing. Old Town provides diverse housing options, from classic walk-ups to high-rise condos

Your Old Town Real Estate Team

Thinking of calling Old Town your home? The MG GROUP specializes in this historic neighborhood and can help you find the perfect place. CONTACT US today to start your search!