5 Things to Look for in a New Chicago Neighborhood

The ecosystem of the Chicago neighborhood has been dissected, reassembled and dissected again over the course of this city’s history. Where one neighborhood ends and another begins is a talking point for every resident when they speak with out-of-towners.

We take pride in our neighborhoods and everyone’s is “the best” because it has “this one restaurant” or a “great little mom-and-pop bar.”

Homes doesn’t exist in a vacuum. Your new home sits on your new street next to your new neighbors. When you are looking for a new home in Chicago, you are also looking for a new neighborhood to adopt as the hub of your life.

So, let’s a take a look at 5 neighborhood factors you need to consider when looking for your new home.

Transportation Options… Or, You Know, Stay Where You Are

This seems like an easy one, and Chicago has a lot of options for transportation. You have bus lines, the El, Metra, location to major highways and proximity to major roads that cut through the entire city (aka Western). But your proximity to these transportation options will be incredibly key to how you will view location.

“I’d say 90% of people in the city take the train to work, so the commute is important,” Wahl Real Estate Group agent and Truepad Trusted Agent Jenna Chandler said.

Living nearer the lake is obviously where you’ll find the most transit options. However, Mickey Hobson, of The Matt Laricy Group (and a Truepad Trusted Agent), points out that living along the blue line, which has directions that go northwest toward O’Hare and directly west toward Forest Park is also a big draw for home buyers.

Both agents said that people want an easy commute to work, easily see family and hang out with friends. Also, in case no one has told you yet, Chicago winters are brutal. A long walk to the train is something you might be okay with in May, but not so much in January. If you are willing to walk a bit further to transit, the prices of properties will go down accordingly. Dream of having a two-flat or rental property? The closer you are to the bus or train, the easier it will be to rent.

Parking, Parking, Oh Parking

Not everyone takes the train—Chicago is very much a driving city. In some areas, typically as you move west from the lake, due to fewer train lines, it’s easier to just drive yourself (or ride with Uber). While not owning a car is a viable option, many transplants coming from surrounding states like Michigan and Iowa like driving, and travel often to see loved ones.

In parts of the city (toward the lake) with many options for public transportation, parking is another animal entirely. Lots of neighborhoods have permit parking, and more trafficked areas have paid street parking. The best option in high-density neighborhoods may be to have your own garage or to pay for a spot in a parking garage.

“Parking is a huge issue, and it’s becoming a bigger issue all the time, because as more people move into the city, parking is more restricted in the streets,” said Truepad Trusted Agent Jayne Alofs. “Always buy the parking if you can afford it. It’s almost a more important investment than the unit itself. If only we could live in our parking spaces…”

Parking can also be expensive—a deeded parking space will cost anywhere from $20,000 to $65,000, depending on where you are—and will need to be considered as part of the monthly cost of owning your home.

Real estate agent Samuel Ciochon said that when looking at condos, buyers should always at least look into options for buying parking. “Parking can have a separate association fee and then there are tax implications as well ($500-1,000/year).”

All About that Nightlife Baby…Or going to Bed at 8 p.m. on a Friday

Almost all of Chicago’s neighborhoods have many, many, many bars. In my neighborhood, it feels like I could throw a rock in the air and hit a beer truck delivery guy any day of the week.

This isn’t bad thing if you are looking for a kicking nightlife. You may want to be at the center of it all and live a block from Wrigley. Or, you may want to exercise the option to live a bit removed from areas of raucous chaos.

As with public transit, access to a nearby walking strip—the downtown of the neighborhood—increases the value of a location.

Michael Gerhardt said, “You have to look at the combination of walkability, nearby restaurants, public transportation, so people can actually get there and will go there.”

If you buy in a spot where everyone wants to be, you have a better chance of selling high later. Look for new construction and restaurants or shops opening up in a neighborhood that is less developed for signs of things to come.

We Like Our Food. Seriously.

Chicagoans take pride in the eclectic and variety of restaurants, eateries, dives and pubs within each neighborhood. One neighborhood, Lincoln Square, for example, can have an amazing Mexican restaurant next door to an old German restaurant, around the corner from a Thai place, all amazing.

Check out which restaurants are close, and which are good enough to be your go-to spot when you don’t feel like cooking that night. Or any night.

We asked agent Jenna Chandler the best neighborhoods for foodies. “The classic spot is the West Loop, near all the Randolph street places [such as Au Cheval, Girl & the Goat]. On the newer side, Ukrainian Village is popular because so much is coming up on Chicago Avenue, and of course Logan Square has lots of places scattered throughout the square and up and down Milwaukee Avenue.”


This is something you may or may not personally have to worry about yet, but it is something many buyers consider when looking for a home in the city.

“Besides transit, if people have young children, or think they’ll have them soon, it’s all about the school district,” Chandler said. “Chicago has magnates and charter schools, but you can’t totally rely on that. If you are buying a place and plan to stay there when your kids go to elementary school, you should have a district school in mind as a backup plan.”

The CPS website has a tool where you can put in your address and it will list all the schools in your vicinity and let you know which school you fall into. Also, check out greatschools.org.

“Not all great neighborhoods have great schools,” Chandler added. “Especially west of the highway, Bucktown, Logan Square, you should definitely investigate,” she said.

Also, if you are thinking of living near a school, traffic in the morning and afternoon in and around schools can be* (aka is) crazy. Depending on where it is, a 5-second drive to the main drag can take 15 minutes.

Bonus: Take a Walk

The most important thing in a neighborhood may end up being the simple everyday things of life.

“Most people are mostly concerned about their location relative to parks and green spaces, groceries,” Jayne Alofs said.

A feeling of walkability in the neighborhood, good (or great) local food shopping, breakfast joints, parks, gardens, and even a little wilderness are key to enjoying the area you live in. So, walk around and check it out, talk to people in the neighborhood, and you’ll start getting to know the place that you might call your home and your neighborhood.

Emily Johnson

Emily Johnson is a writer, researcher, editor, and publishing consultant with a decade of learning in the field. For Truepad she covers real estate trends and develops knowledge base articles that help people learn about the process of buying as they’re looking for a home. She went through the process herself two years ago and is a proud homeowner in Logan Square.

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