Why we love it
It’s the birthplace of modern American improv, where you’ll find one of the world’s most legendary comedy clubs. We also love Old Town for its vintage charm, beautiful boutiques, and late-night buzz.
Old Town is home to comedy star-maker The Second City, which introduced the world to Bill Murray, Chevy Chase, Gilda Radner, Aidy Bryant, Cecily Strong, Mike Myers, Chris Farley, Key & Peele, John Belushi, Jane Lynch, Tina Fey, Steve Carell, and…well, you get the picture. You can catch a live show every night of the week, featuring the city’s top up-and-coming talent.
But Second City isn’t the only reason to explore here. This historic neighborhood is a picture-perfect place to shop on-trend boutiques, dine at historic restaurants, and admire homes in one of Chicago’s most luxurious residential districts. Wells Street is the main drag where you’ll find tons of buzzing spots to eat and drink — it’s a popular spot for bar hopping with the younger crowd.
One watering hole not to miss — Old Town Ale House, a go-to for Second City cast and alums, where you’ll find locals at the bar and the owner’s art lining the walls. For another classic Old Town experience, grab some barbecue ribs at Twin Anchors, a former speakeasy where Frank Sinatra was a regular.
And in June, the Old Town Art Fair brings a ton of nationally acclaimed artists together to showcase their work, drawing a crowd of 30,000 art lovers.
Explore like a local
Stop and smell the flowers at A New Leaf, a gorgeous garden shop and studio. Indulge in the “Old Town Classic,” filled with The Fudge Pot’s chocolate goodies (they’ve been making everything right there on the premises since 1963). Stop by The House of Glunz for a glass of wine; it’s Chicago’s oldest wine merchant, setting up shop more than 120 years ago.
Chicago Greeter: free guided tours
Taste, shop and explore the neighborhoods with a friendly local as your guide. Explore rich histories, diverse cultural traditions and hidden treasures. See sides of the city you may not have adventured out to on your own, and take away a truly authentic Chicago experience. Greeter visits are customized based on your choice of neighborhoods, language and interests.Request a tour with a Chicago Greeter