Top 10 Best Places to Live in the Windy City Chicago

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Contributed by David Galassi, Info Guru

I grew up in Chicago, a 10-block bus ride from Wrigley Field. I lived in a real Chicago neighborhood – the kind of neighborhood that defines Chicago.

Before gentrification and urban renewal, there were generations of families who raised their kids with the same generations of neighbors, raising their kids. In Chicago, there is Chinatown, downtown, uptown and what used to be (before the area code multiplication) the land of the “708-ers” … the suburbs.

Here’s my list of the best places to live in the Windy City, Chicago. Starting with #10 on the list and moving up to #1.

10. Southside

The major drawback to being a Southsider is the implied loyalty to the White Sox. Although rooting for a winner does have its benefits. The southside of Chicago has a lot to offer, from the annual drunk-fest known as the SouthSide Irish Parade, to great, and mostly affordable, neighborhoods like Bridgeport (home to Chicago’s imperial family, the Daleys), Kenwood, Beverly and Pullman. Largely blue-collar, southsiders have made Chicago work.

Population: 9,457
Median resident age: 32.75 years
Median household income: $59,892
Median house or condo value: $630,007

9. Hyde Park

Technically part of the “Southside,” Hyde Park deserves a space of its own. Hyde Park is the home of the University of Chicago and benefited from one of the largest urban renewal plans in the nation during the 1950s. Hyde Park is cool. Kind of intellectual, very urban, and rather exclusive in feel.

Population: 29,764
Median resident age: 33.4 years
Median household income: $48,568
Median house or condo value: $535,834

8. Northshore

The “Northshore” isn’t truly part of Chicago, but the string of suburbs that run from the north boundary of Chicago (Roger’s Park – another interesting neighborhood, although it doesn’t make my list) along Lake Michigan. These suburbs include Wilmette, Lake Forest, Glencoe, Winnetka, Lake Bluff, Highland Park, Evanston, and Kenilworth – where the wealthy families that owned most of Chicago lived. They are still among the most affluent in the nation. If you don’t mind a commute, pick one of these, get a big mortgage and be happy.

Population: 2,513-74,486
Median resident age: 34.3-42.4 years
Median household income: $67,661-over $240,750
Median house or condo value: $371,100-$979,043

7. Wrigleyville

The best part of Wrigleyville is Wrigley, home of the Chicago Cubs, affectionately known as the Cubbies. Living in Wrigleyville is great, unless you have a car, no parking space and somewhere you need to be. Now. Forget about it. Wrigleyville is busy with bars, restaurants, bars, Cub fans, more bars and a great neighborhood feeling. Good access to the CTA – Chicago Transit Authority – which can solve your car issues. The best part of Wrigleyville is that you don’t have to be a Sox fan. At all.

Population: 94,766
Median resident age: 32.85 years
Median household income: $65,840
Median house or condo value: $977,466

6. Printer’s Row

Printer’s Row is a cool new-ish neighborhood immediately south of downtown Chicago (The Loop). It used to be exactly what it sounds like. Lots of huge old buildings have been converted to lofts and luxury residences. The Book Fair is cool – used to be small and is now larger and more bookish. The restaurants and bars in the neighborhood are on the trendy side, as opposed to the “neighborhood” side.

Population: 2,118
Median resident age: 29.45 years
Median household income: $95,362
Median house or condo value: $266,969

5. Old Town

Old Town is one of the older, at-one-time funkier neighborhoods just north of downtown. Right at North Avenue, and south of Armitage, most of the properties have been renovated into pricey single family homes. Shopping is boutique-ish and restaurants are easy to find, although the corner of Armitage and Lincoln has always been a revolving door. You can walk or bike to downtown, if you’re feeling spry.

Population: 10,705
Median resident age: 32.2 years
Median household income: $59,805
Median house or condo value: $1,090,631

4. Evanston

Technically considered the “North Shore,” Evanston has more of a city feel than the other northern suburbs. Evanston has beautiful neighborhoods, terrible neighborhoods, and a thriving downtown. It also has Northwestern University. Northwestern is so close to Chicago – with easy “el” access – that you can be downtown in less than 30 minutes. But why? You have everything you need right where you are. Be careful, some people have suggested that you can live in Evanston and never leave.

Population: 74,486
Median resident age: 34.3 years
Median household income: $67,661
Median house or condo value: $371,100

3. Oak Park

Oak Park, the first suburb west of the Chicago at the dividing line of Austin Boulevard, is often described as “Evanston without the Lake.” Not quite. Oak Park has an awe-inspiring collection ofFrank Lloyd Wright homes (he called this suburb home) and plenty of references to Ernest Hemingway, who called the suburb a place of “broad lawns and narrow minds.” Not so much now. Oak Park is one of the most racially diverse cities in the country, with plenty of alternative – and tolerant – households.

Population: 51,878
Median resident age: 38.9 years
Median household income: $70,602
Median house or condo value: $380,651

2. DePaul

Another neighborhood identified by its university, DePaul is a nice place to raise your family in the city. Beautiful parks, renovated homes, black wrought iron fences and a wide variety of stores, eateries and bars. Parking is no joy, but not as bad as some other city neighborhoods. Definitely high on my list for nice places to live – in the city.

Population: 28,371
Median resident age: 31 years
Median household income: $93,723
Median house or condo value: $901,055

1. Lincoln Park

The perfect view of Chicago’s skyline, a zoo, a farm-in-the-zoo (so you can look at cows and pretend you’re living in the country for an afternoon), the lagoon, beachfront, a botanical garden, dog park and good combination of apartment buildings and single family homes (most of them NOT cheap) … this makes up Lincoln Park. What more could you ask for steps from the heart of the third largest city in the country?

Population: 63,240
Median resident age: 32.1 years
Median household income: $88,143
Median house or condo value: $948,988

Go ahead and disagree. Like I said, Chicago is a city of neighborhoods, and everyone has their own favorite.

I’ve missed lots of them. Even skipped over the western suburbs completely. Add your pick for the best place to live in the Windy City, Chicago is everyone’s kind of town.

Source: all statistics from

4 thoughts on “Top 10 Best Places to Live in the Windy City Chicago

  1. I grew up ALL OVER Chicago too.

    The Southside? Hyde Park? Oak Park? Yeah, only live there if you’re into hookers, drugs ( lots of them ), shootings, gangs… if you’re a criminal or homeless. You’ll love it.

    Oh, and if you’re into trannys and bathhouses, you’ll probably like Wrigleyville.

    If you value your life, move to the suburbs where it’s SAFE.

  2. I can’t quite agree with everything Tom says. The suburbs are not that safe anymore. Houses still get broken into, cars stolen and women raped. If you can afford $3million plus homes then you definitely can live in a safer place but if you are like most people and can’t afford to live on an Estate then you take your chances. But I do have to agree on this…forget Hyde Park (unless you are a politican or wealthy and can afford private protection, don’t bother), the south side has always been tricky and crime very, very high (if you didn’t grow up there, don’t bother) and Oak Park…well, I grew up there and I saw for myself first-hand how it turned downward. Before my parents sold their house, a drug deal happened right in front of our windows. We heard and saw police every day canvasing the streets. I went back last summer and I have to say the best thing we ever did was leave. All I can say is…do your homework and ask a lot of questions.

  3. Hi Tom! My name is Arkisha and I live in Kansas where it is extremely safe! I have a baby and am relocating to Chicago. Your comment moved me most because I intended on moving to Oak PArk! Do you have any suggestions as to where I should move? I care about school district the most!

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