Old Town

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.

Explore like a local

• Grab some barbecue ribs at Twin Anchors, a former speakeasy where Frank Sinatra was a regular.
• In June, the Old Town Art Fair brings more than 200 nationally acclaimed artists together to showcase their work in this popular outdoor festival.
• 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.

Insider tips

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 and 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 The 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 storied local 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 top spot for bar hopping with the younger crowd. Orso’s Restaurant, Happy Camper, Broken English Taco Pub, and Gussie’s Handmade Italian are a few popular options in the area.

Another watering hole not to miss —  Old Town Ale House, a go-to for Second City cast and alums and a favorite of Anthony Bourdain, where you’ll find locals at the bar and the owner’s art lining the walls.

For those with a sweet tooth, stock up on handmade chocolate confections at The Fudge Pot, where everything has been made in-store since 1963.