Where the streets have a name

The 10 most unique stretches of street in Chicago you may have never walked down

By Jeremy Schnitker

One of the neatest things about living in such a big and architecturally significant city like Chicago is that you’re always stumbling across something new.

Every walk, bike ride or drive around the city I’ve taken in my year and a half here, I’ve made some sort of discovery. Be it a breathtaking vintage townhome in the Gold Coast, a quaint, tucked-away café near one of the city’s college campuses, or an old-fashioned tree-lined urban neighborhood that looks like something straight out of an old movie. With all its neighborhoods with varying housing styles and ethnic and economic backgrounds, you can leave your doorstep, walk in any direction, and if you go far enough, see something unique that you didn’t know existed the day before.

Here’s a list of some of the most distinctive stretches of street in Chicago that you may never have experienced — but should.

Fullerton Parkway between Orchard and Clark: This stretch is likely what most of Lincoln Park looked like 50 years ago, as nearly all the red brick rowhouses have been unscathed by modern development. The way the massive old trees bend and dangle just above car rooftops on this part of Fullerton is classic Chicago.

Orchard between Armitage and North: Dubbed “Gazillionaires Row” in a Chicago Tribune article last year, this almost completely redone section of Lincoln Park just east of Halsted now houses some of the largest and most expensive new construction homes in the city. However, many are torn over the aesthetics of this street. The purists, who argue the street no longer has any unifying character, say the gawdy and progressive new home styles are hideous. Say what you want about it, but looking at these massive homes and trying to fathom how much they cost is surreal.

Evergreen between Milwaukee and Damen: The Wicker Park/Bucktown/Ukrainian Village area is getting overrun with new condo developments, many of which are dull carbon copies of one another, turning this once diverse area into an inner-city suburb. But this stretch has been largely untouched. Most of the houses still have old steel gates in front and the yards and well-kept gardens that look like they’ve been there for decades. Literary fans will be pleased to notice renowned Chicago author Nelson Algren called the top apartment at 1958 W. Evergreen his residence for 20 years (there’s a marker outside the brick flat denoting this).

Lincoln from Sunnyside to Lawrence: Effectively the epicenter of the Lincoln Square neighborhood, this section of the Northwest Side feels more like a college campus than many of the actual college campuses in Chicago. Lined with laid-back bars, independent record and video stores, a vintage movie theater (The Davis), as well as a couple cafés, walking these streets reminds you of being in a place like Lawrence, Kansas or Iowa City, Iowa. It’s also a perfect, relaxing getaway to do some window shopping and bar hopping away from the bustle of other districts closer to downtown.

Logan Boulevard from Kedzie to California: The beauty about Logan Boulevard is that it feels like an avenue taken from a prominent neighborhood in any small town in America. These tree-lined streets with large grassy medians represent the northern start to the celebrated Chicago Boulevard District. The massive castle-esque homes that rest placidly along it are some of the most imposing in all of the city. (Logan is just the start of a Northwest Side boulevard district that is fascinating in its entirety — the Kedzie, Palmer and Humboldt sections to the south and west are nearly as charming.)

Astor from Division to North: Almost every historic home on this stretch demands your attention. They’re intricate, turn-of-the-century designs, and the quality in which they’ve been maintained is a spectacle. Despite the fact that it rests just north of the noisy Rush and Division bar district and Lake Shore Drive, you can walk down this street on any given night and feel like you’re in a suburb because it’s so peaceful. That's one of the great things about urban living in Chicago: You don’t always feel like you’re in a big city. This street is a perfect example of that. If money was no object, this stretch, above all in the city, is where I’d want to own a house.

Taylor between Ashland and Morgan: Fifty years ago, before the majority of this heavily Italian neighborhood was ripped out to build the University of Illinois-Chicago campus on the near West Side, dozens of blocks in each direction looked like what this street is now — a collection of old-fashioned, neighborhood restaurants and shops. Now all that’s left is this six-block stretch. But its old-world charm combined with hip college influence still makes it a weekend destination.

MLK Drive from 33rd to 57th: This is probably one of these stretches you’d least expect to have somebody tell you to see it to be inspired, as many Northsiders probably assume this whole area is ghetto. Sure, it can be rough (I rode my bike down it a couple weeks ago in broad daylight on a Sunday and saw a man with his pants down to his ankles relieving himself against a tree less than two feet from the curb). But Bronzeville used to be one of the most prominent neighborhoods in the city (and one of the most prominent African-American neighborhoods in the country), and many of the stately homes from that era are still standing. Some have been turned into slums, and some have been torn down, but there are new breath-taking rehabs going on that show there’s a glimmer of hope for a rebirth to this once renowned stretch of real estate.

57th from Cottage Grove to Lake Shore Drive: This stretch cuts straight through the distinguished University of Chicago campus and takes you right up to the steps of the Museum of Science and Industry. What’s great about walking around in Hyde Park is that, being so far south of the city, you almost feel like you’re in a completely different town. The place has the feel of a quiet little lakeside village with its great access to the beaches of Lake Michigan. The architecture is amazing (both the homes and the campus buildings), and the neighborhood is littered with beatnik cafés and cozy used bookstores that practically beg you to enter.

Lawrence Avenue and Broadway: You can’t help but walk around this little triangle in Uptown and try to imagine what this area looked like in the 1930s and ’40s, when it was one of the most bustling theatre districts in the world and gangsters were stumbling in and out of the Green Mill (which was frequented by Al Capone). Many people have been to this area to see concerts at the Aragon and Riviera, but they usually jump right back on the Red Line and head south after the show. Next time you’re up there, walk around a little and try to soak up some nostalgia.

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