Old Town

Old Town forms a family-friendly and relatively low-density enclave within striking distance of the center of Chicago, so it’s no surprise that growing families are flocking there seeking Old Town real estate in increasing numbers.

Things to Do in Old Town

Old Town offers plenty of things to do, whether you want to enjoy a picnic in the sun or take in a show.

The Bauler Playlot Park occupies half of a block on Old Town’s western edge, with slides, swings, and a jungle gym for your kids and plenty of open grass, so the area forms a natural hub for the community on warm summer days. You’ll also be able to enjoy more cultural activities, including the annual Old Town Art Fair. Drawing visitors from all over Chicagoland, it showcases hundreds of art pieces by nationally renowned artists, from traditional paintings to mixed-media masterpieces.

One of the most well-known attraction would have to be The Second City. An internationally known comedy theatre, it performs hilarious improv sketches to sold-out audiences Thursday through Saturday, and even runs student productions on its third stage.

Top Restaurants and Bars

Old Town offers some of the best food in the city. For Italian fine dining, try the Topo Gigio Ristorante. Winner of the International Food Manufacturer’s award for Culinary Excellence for the past 17 years, it provides diners with unparalleled dishes, including grilled calamari, conchiglie alla sarda, and tortellini alla Panna.

For something more homegrown, enjoy a blend of American Traditional and American New at Old Town Social, where you can pick up mac and cheese, duck wings, or a pork belly sandwich. If you’re in the mood to experiment, there’s no better option than Café Sushi, where master chefs create complex dishes for the connoisseur and sushi apprentice alike.

Old Town’s bars put up stiff competition, especially The Glunz Tavern. With a history reaching back to 1888, this 48-seat bar enjoys an old-time atmosphere complemented by an extensive array of wines, beers, and spirits. If you’re looking to take in the game in a friendly atmosphere, try The Benchmark. It offers 12 draft and 34 bottled beers, and even boasts a retractable roof to let the sunshine in during the summer.


Old Town’s popularity with families is bolstered by a large range of educational institutions, including:


Old Town is bordered on the north by W. North, on the south by E. Division, on the east by N. Clark, and on the west by N. Larrabee. The neighborhood is cozy enough to cross with nothing more than your own two feet, but there are also several public transportation options to take you further afield. The CTA Brown and Purple lines both run from Sedgwick Street, taking you into the Loop in about 15 minutes. The extensive bus system makes local travel easy; take the 72 to neighborhoods like Wicker Park and Bucktown, or the 73 to the popular Armitage Avenue shopping district in Lincoln Park.

Find Old Town Real Estate With Chicago Home Partner

At Chicago Home Partner, our agents can help you find Old Town real estate that will meet your needs. We’re able to locate houses, condos, and rental opportunities, so feel free to contact us today for more information concerning this popular area of the city.