Should you move to Old Town Chicago?

Old Town is a neighborhood located on the near north side of Chicago and remains popular because of its location, nightlife, exciting activities, and beautiful housing options. Properties in Old Town, Chicago can be on the higher end of the budget, but it is a prestigious area to live.

Old Town History

Old Town is a relatively small area and used to be known as one of the country’s most dangerous public housing projects, Cabrini Green. At its peak Cabrini Green was home to 15 000 people. Over the years crime and neglect created hostile living conditions for many of the residents who lived there. Chicago Housing Authority began tearing down the mostly run-down mid- and high-rise buildings with the last high-rise demolished in March 2011. Today only the original two row houses remain.

This area has become the site of major redevelopment plans due to its close proximity to downtown, resulting in a combination of upscale high-rises and townhouses, with some units being owned by the Chicago Housing Authority for the goal of creating a mixed income neighborhood.

Old Town Location

This location cannot be beaten. Old Town sits less than two miles north of the heart of downtown Chicago, and just a mile west of the lake. The neighborhood comprises sixty-four acres, its original and modern borders split by North Avenue, running straight through the center.

Many locals say, “Wait! half of that is Lincoln Park.” And they’re correct. Depending on who you ask, a good chunk of Old Town that lies north of North Avenue is also considered Lincoln Park.

Old Town takes its neighborhood status seriously — you can feel it when you stroll down its tree-lined sidewalks. There is a sense of community that’s so often lost in urban neighborhoods.

It is a fantastic area, showcasing mostly historic, human-scaled buildings as opposed to high-rises with good options for both ordinary shops like grocery stores and more fun, unique boutiques. It’s close to the Lake and the south end of Lincoln Park, walking distance to the Magnificent Mile, and a relatively easy commute to the Loop.

Old Town Entertainment & Festivals

The Old Town neighborhood is home to some of Chicago’s top entertainment. If you are looking to laugh the night away, check out Second City, which hosts popular sketch shows and improv classes. Some iconic faces appearing here over the past 50 years include Dan Aykroyd, Chris Farley, Julia Louis-Dreyfus, Tina Fey, and Mike Meyers.

Another well-known comedy club is Zanies. This comedy club hosts nationally known stand-up comedians seven nights a week.

New City is a popular shopping, eating, and entertainment destination in Old Town featuring movie theaters, Kings Bowling, Saks Fifth Ave Off 5th, Dick’s Sporting Goods, and restaurants like Earl’s Kitchen and Yard House.

The Old Town Art Fair has been an annual event for over 70 year. Crowds flock from near and far to attend one of the best art shows in the country. Over 250 juried artists are invited to participate each year and it’s estimated over 30,000 visitors attend.

Old Town is also home to The Wells Street Art Festival held the same weekend as the Old Town Art Fair (second weekend in June) and takes place on N. Wells Street between North and Division. This festival is all about fun and entertainment. Created by the Old Town Merchants and Residents Association, the festival has 200+ art vendors and raises over $300,000 for Old Town community causes like hunger initiatives and workforce programs.

Old Town Restaurants & Nightlife

Old Town is home to some of the best restaurants and innovative foodies in the country. From Italian to Mexican, you’ll find something to please every palate.

To keep with the history of Old Town, Twin Anchors is an old-school tavern and barbecue restaurant opened in 1932. This historic restaurant gives off a bit of a gangster vibe and was once frequented by Frank Sinatra. Twin Anchors is best known for the ribs which are broiled, not smoked.

If you’re looking for a great dining experience while still watching the games, check out Old Town Pour House. Although it looks like your typical bar on the outside, Old Town Pour House should not be skipped, especially by any beer connoisseurs. The bar has one of the biggest and best beer selections in the entire city, with 90 craft beers on tap. If you’re not a beer drinker, you should be happy to know that Pour House also has a selection of wine and whiskey, as well as a full menu.

Old Town also hosts Chicago’s first sushi restaurant, which opened in 1967, called Kamehachi. Make a reservation and enjoy the extensive menu of grilled seafood, steaks, salads and a variety of new maki and sashimi offerings.

For more than 30 years, Topo Grigio has been an Old Town restaurant landmark for Italian-American cuisine. Whether you’re seated in the garden patio or the cosy dining room, the hearty Tuscan inspired dishes will have you wanting to return. Kick back with a plate of pasta or even just a glass of red wine and observe the vibrant Wells Street foot traffic.

Broken English combines a unique twist on Mexican street-style tacos, refreshing beverages, great music, and vivid artwork created by local talent. The small plate tacos and margaritas always make for a great night!

If hearing about all these amazing places has made you want to move, you’re probably wondering what housing options are available in Old Town. The good news is there are several luxury apartments and condos waiting for you. Apartments in Old Town are undeniably world-class, and also provide easy access to all of Chicago’s favorite spots.

Old Town Housing Options

If you want to live in a historic environment with an abundance of places to try, then Old Town is the neighborhood for you.

Make sure to check out the K Square, located in Chicago’s Old Town Triangle at 1749 N. Wells Street. It is a premier apartment community featuring unique floor plans ranging from studios to spacious two-bedroom apartments. Community amenities at K Square feature on-site maintenance, package receiving, off street parking, pet area, dog run, lobby, laundry facilities, high-speed internet, heated garage, bike racks as well as newly renovated amenities including a state-of-the-art fitness center, community lounge, and pool.

Apartments at K Square feature efficient stainless-steel appliances, central air and heat, spacious closets, extra storage, and unparalleled views of the city.

Next is the Old Town Park, located at 1140 North Wells Street. The property is located centrally close to dining, shopping, and nightlife right on Wells Street. This 32-story tower features studio, one-, two- and three-bedroom floor plans. Enjoy an outdoor escape with a heated pool, hot tub, loungers, and daybeds.

We also have The Scott Residences, at 211 W Scott Street. This gorgeous building sits on bustling Wells Street, in the heart of Chicago’s popular Old Town neighborhood. The building features convertible, one-, two- and three-bedroom layouts. The Scott has a great amenity rooftop deck with panoramic views. Property highlights include a club lounge, demonstration kitchen, fitness center, rooftop sun deck with grills and fire pit, valet dry cleaning, billiards, bike racks, storage lockers, package receiving, and a private dog run.

The 1225 Old Town is a vibrant luxury residence at 1225 N. Wells Street with easy access to nearby boutique stores, local vintage shops and plenty of dining and entertainment. They offer convertible one-, two- and three-bedroom layouts with gorgeous luxury finishes. It is a pet-friendly building and boasts stunning balcony views. Make sure to check out the roof deck pool during one of the gorgeous sunsets.

Old Town Green Space & Exercise

If you love to spend your time outside, then Old Town is a great place to call home. Surrounded by green space, you’ll have plenty of options when the sun’s out. We have Seward Park and Lincoln Park both located along the lakefront of Ohio Street Beach. You have Lake Michigan at your disposal providing all the views, plus easy access to water activities.

Thanks to its proximity to major hubs like The Loop, transit, shopping and conveniences, having a car is optional when living in this neighborhood. In fact, Old Town Park has a walk score of 98, and a transit score of 90.

Speaking of walking, fitness facilities are abundant and if you love to workout, you’ll have no shortage of options. Equinox, Formula Fitness Club, Shred415 and SoulCycle offer a variety of classes to get that heart rate up.

Old Town Shopping

Get ready to shop ‘til you drop! Old Town is home to some of the best gift shops, fashion boutiques, and local artisanal stores in the city. This includes Fleet Feet, Handle With Care, Judy Maxwell Home, and so many more.

The Best of Old Town

Truly this neighborhood has everything in one place, filled with entertainment, food and accessibility at its finest. It has stores galore, some of the best restaurants and the transit system will get you from Cubs Socks Bulls and Bears games with ease.

If you’re ready for your own personal tour of Old Town, your next step is to call, text, or email so we can get together to create your plan of action to find your new home.


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