Old Town

Has a vintage charm and laid-back atmosphere with many coming to spend their days meandering through the neighborhood.


Welcome to Old Town

A quaint and quiet neighborhood with artisanal shops and beautiful architecture.
Don't let the name fool you, Old Town is an exciting neighborhood. Old Town has all the old school charm Chicago is known for alongside amazing architecture and well-known places to see. You can find pubs and clubs alongside creative coffee shops and original buildings. Old Town has a wealth of Victorian-era buildings to marvel at, making it one of the most unique areas in the city. Between the artisanal coffee shops and distinct boutiques, Old Town Chicago has a slow pace of living, perfect for your next home. You’ll find the resilience of the residents shines through in areas like St. Michael's Church, one of the only structures to survive the Great Fire of Chicago. Old Town is also known for Second City, a world-renowned comedy club that has stood for years as the pinnacle of humor. Old Town has a vintage charm and laid-back atmosphere with many coming to spend their days meandering through the neighborhood. 

What to Love 

  • Old-world charm and modern amenities. 
  • Beautiful tree-lined walkways. 
  • Some of the best coffee shops in Chicago 

Local Lifestyle 

Old Town has a relaxed atmosphere with many locally owned venues and entertainment options. Besides the cool cafes and coffee shops, you can find comedy clubs, parks, and beautiful architecture. Old Town is unique in its options of things to do with traditional Chicago favorites and new experiences. Old Town is also near the Garfield Park neighborhood with old war-era brick buildings.

Dining, Entertainment & Shopping 

Wells street operates as Old Town's main street where you’ll find plenty to shop, see, and do. Old Town Ale House is a popular local watering hole where many Second City cast and students can be found winding down after a set. 
Utopian Tailgate is, as the name suggests, a lively tailgate-themed bar. There are bar games, picnic tables, and a faux football turf to complete the vibe. The food is elevated party fare with sliders, wings, and nachos on the menu. Butch McGuire’s is a high-energy bar with trivia nights, and other themed party events. The food is traditional pub fare, but the brunch comes with bottomless mimosas.
The Topo Gigio Ristorante serves traditional Tuscan-style Italian with light tomato and basil sauces or tomato and cream sauce. Their outdoor patio is in a beautiful garden. They also have a banquet room available. 
The closest luxury shopping mall is at 900 North Michigan Shops with seven levels of boutiques, luxury retailers, and a Topgolf Swing Suite. Just a few of the brands you will there are Gucci, Kate Spade, Bloomingdales, and Tesla.

Things to Do

The revered Second City comedy club is likely the most famous venue in Old Town and the most famous Comedy Club in the Midwest. Many famous comedians have cut their comedy teeth here, and you can still catch a show every night of the week. 
Old Town Art Fair is an annual event in Chicago’s historic triangle district. It is a huge event with 200 plus vendors from all over the country. There is also a children’s corner, live music, and food vendors. 
St. Michael Catholic Church was built in 1852 and is one of the few buildings to survive the Chicago Fire in 1871. It is a gorgeous church with painted, domed ceilings and stained-glass windows.


The Chicago Public School system, along with private schools in the area, serve the community of Old Town. 

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Work With Quentin

Long on going relationships are the reason I love this job so much. Being able to see someone's face light up as I hand them the keys to their very first house is what gets me up in the morning.

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