Old Town

Neighborhood Scores

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Old Town Chicago Luxury Apartment

What Its Known For

Luxurious homes
High-end shopping and dining


Very luxurious and high-end
Thriving night life scene
Charming historic feel


Rent tends to be high


Old Town’s proximity to its upscale neighbors, Gold Coast and Lincoln Park, has led to its gradual evolution into a popular destination for shopping, dining, and scenic strolling. A 1920s artist’s haven turned 1960s counterculture hippie hotspot, this neighborhood has an eclectic history, visually blending the “then” with the “now”.


Wells Street is where most of the action takes place—here you’ll be able to find specialty shops, tons of restaurants, and some of the best bar-hopping in the city. This neighborhood is also home to the legendary comedy club, The Second City, where they host shows every single night. Keeping true to its artistic roots, Old Town has plenty of entertainment options for creatives—head over to an immersive art installation or peruse work from artists all over the world at the annual Old Town Art Fair.

The name “Old Town” rings especially true when it comes to the area’s architecture—this neighborhood is home to some of the city’s most historic buildings, including St. Michael’s Church, a Victorian-style gem that managed to survive the devastating Great Chicago Fire.

While Old Town is a super walkable area, you’ve also got a variety of bus routes and the brown, purple, and red CTA lines running through the neighborhood for convenient travel around the city.


Old Town’s charm makes it an incredibly sought-after place to live—meaning you should expect higher rental rates when looking for an apartment in the area. Most options are newer high rises and luxury apartment complexes.

If you’re looking to move to Old Town, we know all of the best spots to tour. Go ahead and pair up with a Smart City agent for personalized help navigating your Chicago apartment search!

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This is the best spot for a night on the town!

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