Friday Feature: Old Town

chicago real estate old townIf moving to the hottest neighborhood in the country sounds appealing to you, then check out the Chicago real estate in Old Town. According to, the Near North Side neighborhood is the most up and coming place to live in America. The ranking was compiled based on the website’s zip code searches, and Old Town came out on top. The neighborhood is notable as the home to the infamous Second City theatre, but there’s more than laughs that attract so many people to this part of town. Old Town is also home to historic, Victorian-era buildings, a plethora of unique shopping and dining and great entertainment that includes the Steppenwolf Theatre and Royal George Theatre.

The median home price for a single-family home in Old Town is $207,000, a bit higher than the Cook County average of $155,100. However, living in such a vibrant neighborhood certainly makes the extra cost worth it. Prospective homeowners can choose from Brownstone walk-ups, single-family Victorian style homes or newer condos. There are currently 70 homes for sale in Old Town with prices ranging from $122,654 for a one bedroom and one bathroom condo to $3,199,000 for a four bedroom 5,000 square foot home. Old Town home values have also increased more than 8 percent in the past year.

Average rents in Old Town are as follows:
Rent for a studio apartment-$1,200
Rent for a one-bedroom apartment-$1,425
Rent for a two-bedroom apartment-$1,825
Rent for a three-bedroom apartment-$2,500

Old Town has a population of 10,791 with a median household income is $59,805. According to WalkScore, the area is the fourth most ‘walkable’ in Chicago, with a ‘walkability’ score of 95. Old Town is also noted as being the second safest neighborhood in Chicago, according to NabeWise, and is even one of the top ten neighborhoods for singles. So whether you’re a young professional or a growing family, Old Town can certainly fit your needs.

Old Town is served by the Chicago Public School district and 53 percent of students in the neighborhood are enrolled by CPS. The area is home to the LaSalle Elementary Language Academy, a CPS school which enrolls students in kindergarten through eighth grades. LaSalle received a GreatSchools rating of 9 out of 10 and prides itself on offering students a choice of four world languages: Spanish, Italian, French and Chinese. World language education and expanding students’ knowledge of other cultures is an integral part of the school’s mission statement.

Another notable school in the area is Walter Payton College Prep High School, a magnet school that is on Chicago Magazine’s list of the top 15 high schools in Chicago. Additional accolades for the school include: U.S. News and World Report’s Top 100 High Schools (’07, ’08, ’09, ’10, ’11), Newsweek Top 50 High Schools, Intel School of Distinction and the Goldman-Sachs Foundation Prize in Excellence in International Education.

Nearby private schools include: The Latin School of Chicago, Catherine Cook School, Lincoln Park Preparatory Preschool and Kindergarten and Immaculate Conception St. Joseph School.

The Latin School of Chicago enrolls elementary, middle and high school students and focuses on embracing diversity of people and ideas. The Catherine Cook School enrolls students from preschool to eighth grade and focuses on project-based learning supported by innovative technology.

Lincoln Park Preparatory Preschool and Kindergarten allows children aged two through six to build strong self confidence and a commitment to learning. The Immaculate Conception St. Joseph School serves students in pre-kindergarten through fifth grade and provides a challenging and innovative curriculum.

Looking for some of the best shopping and dining in Old Town? First off, it doesn’t seem right to narrow down a rich neighborhood to such a few selections, so these picks are just a small handful of what Old Town has to offer.

Eat and Drink

  • Old Town Pour House. Located on Wells Street in the heart of Old Town, this bar and restaurant offers more than 90 beers on tap. Be sure to come hungry and thirsty to enjoy everything from seasonal IPAs to amber ales and baked truffle mac and cheese or Guinness braised short ribs.
  • Mama Milano Pizza Bar. A boutique pizzeria that features stone oven and Neapolitan pizzas plus a great wine selection. Don’t pass up the opportunity to try Mama Milano’s famous spinach bread!
  • Bistrot Margot. Offers traditional French dining in a warm atmosphere. Be sure to try their trademark French Onion soup.


There are so many great boutiques in Old Town that whether you’re looking for that perfect painting for your mantel or a gift for your pet you’ll be able to find what you need. Here are some unique picks:

  • UpDown Cigar Shop. In business for more than 45 years, this shop offers the city’s most extensive collection of cigars, pipes humidors and accessories.
  • String on a Strand. A one-of-a-kind store frequented by crafters and wholesalers, String on a Strand features one of the city’s most impressive collections of beads and hand-crafted jewelry. Be sure to check out their classes as well.
  • Handle with Care. An upscale women’s clothing and accessories shop that has been in the area for more than 30 years, Handle with Care sells every day wardrobe pieces and special occasion outfits.

Be sure to visit for more information.


  • Second City. You’ve most likely already heard of the infamous improv comedy theatre, as it was the starting ground for a variety of SNL alums. Bring friends or family to a show or check out their classes.
  • Zanies. Enjoy some hilarious stand-up comedy in the heart of Old Town.
  • Steppenwolf Theatre. A Tony-award winning theatre company that supports the work of aspiring and mid-career playwrights.


  • CTA: Brown and Purple line trains.
  • Airports: O’Hare International Airport is 30 minutes away via car and about an hour away via the Brown and Blue “L” lines. Midway International Airport is about 25 minutes away via car or an hour via the Brown and Orange “L” lines.
  • Highways: Access the suburbs via I-90 or I-290.
  • Parking: Finding a spot can be a little tricky on more residential streets. Try using a website such as SpotHero to find a place to park.

Several top-rated schools also make this community a smart place to settle down. Plenty of bars, restaurants and unique boutiques plus some great local theatre means you’ll never be at a loss for excitement if you live in Old Town

For more information on popular neighborhoods for new homes in Chicago, click here.