Best of Chicago

Three top Chicago neighborhoods for nightlife and culture

Every year, both The Chicago Reader and Chicago Magazine publish Best Of lists to showcase favorite local attractions, establishments, people, and whatnot. One publication uses votes cast by readers (as well as “a slew of critic’s picks”) while the other counts on its editorial team to determine who and what lands on the list. If you take a look at both, you’ll see some overlap every year.  And if you take an informal poll amongst yourselves and your buddies as we did, you’ll likely see some overlap there, too.

In other words, while the Best Of lists can never include everything that’s good, great, and wonderful, those bars, restaurants, and galleries that do make it always have something special that draws people in.

The same is true for neighborhoods. Here, we present three Chicago neighborhoods (two on the West Side, and one on the South Side) that keep showing up on Best Ofs again and again, particularly for their access to nightlife and culture. And because great bars, music venues, and art outposts are hallmarks of urbanism, we knew you’d be interested in what kind of property you can purchase in those areas. So we did some Zillow trolling for you and gathered examples of real estate on the market now. *

Wicker Park (West Side)

Over and over, this hipster-haven lands on every Best Of list out there.  Forbes calls it the “Midwest Mecca of Hipsterdom.” It’s also been named the top pick ‘hood for nightlife in the Chicago Reader for many years in a row. Wicker Park is easily the most famous of the neighborhoods that make up the larger West Town. Best

Current Wicker Park listings:

 Single family home:

–                Square feet: 4300

–                Bedrooms: 4

–                Bathrooms: 4.5

–                Features: 3 levels, dark hardwood floors, 5 outdoor decks, 3 wetbars, 2 steam showers

–                Price: $1.75M


–                Square feet: 1259

–                Bedrooms: 2

–                Bathrooms: 2

–                Features: Top floor penthouse, open floor plan, cathedral ceilings, private balcony

–                Price: $349K

Pilsen (South Side)

For several years in a row, this neighborhood has won the Reader’s top spot for culture and for the first time this year, affordability. One commenter said, “This area is just itching to be gentrified.” And just last month, Chicago Magazine posted video tour of the neighborhood on their website, which showcases some of its history, murals, “outposts for coffee snobs,” and other delights that give the area its draw.

 Current Pilsen listings:


–                Square feet: 919

–                Bedrooms: 2

–                Bathrooms: 1

–                Features: 14-ft timber ceilings, original brick walls, private terrace with southern view, designer light fixtures.

–                Price: $240K


–                Square feet: 620

–                Bedrooms: 1

–                Bathrooms: 1

–                Features: 12-ft timber ceilings, brick walls, skyline views from balcony, underground parking

–                Price: $185K

Logan Square (West Side)

One of our buddies calls Logan Square the coolest “hipster adjacent” neighborhood for its proximity to Wicker Park. Like the perpetual bridesmaid, it also comes up in the Chicago Reader over and over again as “runner up” to both Wicker Park and Pilsen in different categories. When it comes to real estate, though, sometimes buying a place in the second best neighborhood gets you first-rate deals – especially when it’s adjacent to top dog – because you get access to the perks without paying the full premiums.

 Current Logan Square listings:

Single family home:

–                Square feet: 4000

–                Bedrooms: 4

–                Bathrooms: 3.5

–                Features: Hardwood floors, upgraded kitchen, yard and deck, spa-like master suite

–                Price: $$675K


–                Square feet: 1080

–                Bedrooms: 1

–                Bathrooms: 1

–                Features: Loft layout, exposed brick and ductwork, large windows, lots of light

–                Price: $245K

*October 2014

Photo credit: Lucy Hewett

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Elizabeth Salaam
Along with her work as Senior Contributing Writer for Girl's Guide, Elizabeth Salaam writes for the San Diego Reader. Her work has also been published in Elle Magazine. | Most inspired by: Contradictions. | Favorite room in my home: The Master suite. The windows have views for days! | Best design idea I may never do: Adorn my enclosed toilet room with library book wallpaper and a chandelier. | Will never: Bungee jump. | Have always been: Rebellious. | Dying to: Live in a Paris flat with herringbone wood floors.
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