Old Town

Part chameleon, part time capsule, Old Town is a historic neighborhood that’s fluent in the art of reinvention.
If downtown is the heart of Chicago, Old Town is the funny bone. Here, you’ll find some of the city’s hottest comedy clubs, including The Second City and Zanies. This part of Chicago is old school—dating back to the 1800s. Since the beginning, Old Town has gone through many reincarnations, hitting that sweet spot between modernization and lived-in character that Chicago does best. Today, Old Town is home to eclectic shops on Wells, tight-knit entertainment communities, and all the Mom & Pop restaurants you could ever dream of.

Let me show you Old Town

Where is Old Town?

How to Get Around



No car needed day to day. Everything is right here!



Take the Brown, Red, or Purple lines, buses, taxis or ride shares.



Consistent bike lanes make biking here a breeze.

You'll Like This Neighborhood If...


   What's cool in Old Town?   

From bars that Anthony Bourdain once called “perfect” to legendary shows at Second City, I know I made the right decision to choose Old Town. It’s full of history, beautiful streets, and being so close to the lake has been a game changer!

- Old Town Local

Twin Anchors Bar & Tavern

Twin Anchors Bar & Tavern

Stop by this family-owned operation for delicious ribs and a friendly staff that always treats you like one of the regulars.

Wells on Wells

Wells on Wells

Find all of your favorite brews on tap at this neighborhood bar with an outdoor beer garden.

Arclight Cinemas

Arclight Cinemas

Catch a flick at this Old Town theater. Parking validation and a full bar make this a local favorite.

Market Fresh
Experience the best home-spun comedy venues Chicago has to offer. See where comedy giants like Tina Fey, Amy Poehler, Bill Murray, and Stephen Colbert cut their teeth and be on the lookout for more rising stars just hitting the Chicago comedy scene.
Old Town is known for its multigenerational spirit. Check out some of the best down-home places to eat that have been passed down to children and grandchildren one delicious recipe at a time.
  • The Fudge Pot
  • Pop’s Italian Beef & Sausage
  • Mama Milano Pizza Bar
  • Old Jerusalem Restaurant
Mom & Pop Shops


Places to Get Hammered


From public houses to dive bars, it’s easy to find a new favorite spot for drinks and debauchery. Whether you’re into beer, wine or liquor, this historic neighborhood really knows how to throw one back in style.
  • Old Town Ale House
  • Old Town Pour House
  • Old Town Social
  • Benchmark

Recent Listings in Old Town