Revisiting Uptown

It’s been far too long since I’ve spent any length of time in Uptown, and I’ve decided to remedy the aching void that’s produced in me. More accurately, I wanted to check out Uptown’s ad sales potential for our magazine and our recently-launched New Home Notebook site.

Today’s visit consisted of several hours walking and driving. I’ll be back in Uptown several times over the next two weeks, and posting more video and photos from today’s and subsequent visits.

Until then, join me for a drive along Kenmore Avenue in the Buena Park section of Uptown.


  • Where’s IrishPirate at?

  • Sheridan Parker 11 years

    What a pretty stretch of Kenmore. Easily one of the nicest streets in Uptown.

    I personally hope Wilson Yard stays vacant until 2011 when a new alderman can reshape it into something that actually makes sense. Far better than placing two towers of subsidized housing alongside a still UNCONFIRMED Target.

    Look, the more realistic minded condo owners around here understand there is a huge inventory of subsidized housing in Uptown that won’t fully turn over for decades. This place will always be diverse. Some of us moved here for precisely that reason. But there is room in that reality for progress. Why doesn’t our alderman understand this?

  • Levois,

    If we can take him at his word, he’s too pale to be caught on camera. He may have been in the Jewel buying some cheap wine. Or perhaps he’s summering in Downers Grove.

  • Brian 11 years

    Do you mean the alderman is buying cheap wine, not Irish Pirate? Maybe that’s why her pet project isn’t getting done but at least she’s bonding with her constituents.

  • Levois,

    I was drunk and sleeping off that cheap wine Joe Zekas referenced. I buy it in bulk when it is on sale and carry it home on my Radio Flyer wagon. Don’t mention “wagon” to me though. Makes me think of 12 Step meetings.


    I summer in Tinley Park, NOT Downers Grove. As if………

    That “apartment hotel” you referenced and its immediate neighbor are both renovated apartments now. No real problems. Almost all the older 6 flats are now condos. I’m aware of one north of Buena that hasn’t been converted and two or three south of Buena. They seem to be owner occupied though and are fairly well maintained. The smaller number of 2-3 flats seem to be owner occupied and if you count the two buildings on Buena and Kenmore there are upwards of 190 newer condo units built since the late 90’s from 4000-4400 N. Kenmore. That would be counting 24 units of condo quality post college frat boy center entrance housing “Gibbons Management” built in the 90’s. Time to sell those to quiet condo owners.

    There are loads of children in the area. Typically they travel with their parents or nannies on trikes, big wheels, and most often strollers. A fairly new phenomena here is double baby strollers. If your camera had panned off to the right or left you would have noticed many strollers, children’s toys and wading pools sitting behind wrought iron fences in the condo buildings.

    Depending on when you are on Kenmore it can be loaded with kids, dogs, or people walking home from work. Sometimes all three. As one of my long term neighbors said to me a few weeks ago “this street has CHANGED, there are actually people coming home from work”.

    Your description of Kenmore in the late 80’s and into the 90’s is accurate. If anything you don’t portray the true desolation that Kenmore was. I was here and it was nasty. Although by about 1992 the worst was past. Many of the problem buildings were torn down, great waste of older graystones, and their residents were largely dead, gone or both.

    The movie “The Hunter” with Steve McQueen from 1980 has a great scene filmed around 4100-4200 Kenmore. You see Uptown in all its glorious multi racial ghetto past. At that time it may have been one of the most dangerous streets in Chicago because of the poverty, racial diversity, and gang problems. If you are going to live in a gang infested area better it be one homogeneous gang as opposed to rivals of 3-4 different ethnic backgrounds.

    I’ve looked for that scene on YouTube and unfortunately only bits are shown in a trailer. Bit of Kenmore at 34 seconds in.Nothing better than seeing Steve McQueen jumping from Kenmore rooftop to rooftop and then ending up sending a car careening off Marina City into the river. Just another day starting in Uptown.

    As for Wilson Yard it may be about to start or not. We peon taxpayers are not worthy of being informed of what our tax dollars are doing. Target seems to be close to signing a deal and the two towers of subsidized housing may not be far behind. One tower for seniors and one tower for families. Ultimately I don’t expect either tower to cause many problems because generally Holsten Management does a good job managing subsidized housing. If only through years of learning how to the hard way.

    My biggest issue is the idea of building a major retailer and NOT directly tying in a needed renovated EL stop. Absolute criminal stupidity that could only happen in a Chicago where “da mare” is more concerned with 100 percent aldermanic support than real planning. The lil’ guy must have a very fragile ‘wittle’ ego to crave absolute slavish devotion so wholeheartedly.

    The infrastructure of this city is slowly falling apart and he is planning Olympics, which I support, and trying to figure out how to stay two steps ahead of those nasty Fed G-men. It must be difficult running a city and making sure your extended family does well financially with all those feds poking around.

    Go Feds!

  • IrishPirate,

    Thanks for the extended riff on Kenmore.

    I didn’t go into detail on the Desolation Row meme because the transformation has been so complete. Two brief Kenmore vignettes from the late 80s:

    A broker friend was standing outside a condo conversion, talking with a young lady he’d just shown a unit, when a body landed on the sidewalk not far from them. A drug dealer had stabbed his girlfriend to death in mid-afternoon and dumped her from a third-floor window. No sale.

    The night before a coordinated open house event teenage entrepreneurs stole the newly-installed sod from in front of 3 or 4 buildings. They showed up early Sunday morning, sold the sod back to the developers, and re-installed it.

  • The Uptown Update ran a link on this post. You can expect a well viewed video.

  • UptownR 11 years

    I just walked my stroller up Kenmore last night past the IrishPirate’s place… It’s become one of the nicer streets in Southern Uptown for a stroll, and the Buena Circle Playlot has been great for families in the area. And there were bodies falling at my feet.

    I think Uptown has some of the best six-flats on the North Side (especially on Kenmore and in Sheridan Park), and this is one reason the condo conversions will continue. If you look at condos in Lakeview and Uptown, the units in Uptown are usually larger and still offer a pretty good price break per square foot. And much of Buena Park is just as nice if not nicer than northern Lakeview. Sure, we’ve still got the drunks hanging out on Broadway, but the Hotel Chateau in Lakeview is quite a bit worse.

  • UptownR 11 years

    I meant to say there were “NO bodies falling at my feet”. Hah!

  • Dan 11 years

    Nice video of Buena Park. 100% different feel from the rest of Uptown. Try venturing North of Montrose on Kenmore and the family friend atmosphere fades away.

    So, great video of how nice Buena Park has become, but the rest of Uptown still needs some major work.

  • Thanks, Dan.

    You’re correct that much of Uptown is still Uptown, and is likely to remain Uptown for a while – even if you call it South Andersonville or, as one broker is billing northern Uptown, “the heart of Andersonville.”

    I’d say that Sheridan Park has also become pretty generally civilized. See my video of that area, of Kenmore north of Lawrence, and more Uptown video on our YouTube playlist. I’ll be adding yet more Uptown video over the next several weeks.

    Castlewood Terrace is a gem of an area, and always has been – one of the most attractive long blocks in Chicago. There are other isolated pockets off of Marine Drive that have slipped the surly bonds of Uptown. And, Uptown takes on a different character west of Clark Street. Most folks, from what I understand, are calling that part of Uptown Ravenswood since it’s closer in character to that neighborhood.

  • Sheridan Park is “generally” civilized and the housing stock is also on average better than neighboring Buena Park. The six flats are larger there and typically on deeper lots. Some of the most beautiful six flat graystones in the city exist there.

    The problem they have is a large number of scattered site CHA housing sites and other subsidized buildings. It is not uncommon for there to be drug dealing and violence associated with some of the people who live in those buildings. If those buildings get hardcore tough management and screening the neighborhood will become much more livable for everyone. At some point that will happen as the law abiding folks living in the subsidized housing are starting to complain more vocally. It may even be happening now as there was a recent shakeup at the property management company. Time will tell if any changes are lasting and meaningful.

    Right now there is apparently some gang war going on over drug turf and shootings are unfortunately common. When you have gangs shooting in public parks, Broncho Billy Playlot for example, and innocent Truman students are murdered while walking it flat out scares people. When people are afraid to walk outside after 5 PM with their kids it’s time to take some effective action.

    Uptown Crime Blotter.

    Long term I suspect the main problem Uptown will face is cleaning up the larger subsidized highrises off Wilson, Lawrence and on Leland. The smaller buildings are easier to get control over and the market rate housing is generally being cleaned up over time.

    It is possible to manage a CHA highrise, but the political will and expertise has to be there.

  • Sha ninja 3 years

    I remember kenmore Ave I lived on kenmore for a year and a half I was 8 when I moved there I was 9 1/2 when we moved it was a very dirty street at the time several building were either being torn down or needed to be I lived in the apartments across from the Catholic School I saw some thing that a child should never see my father was friends with the kenmore boys that was around 33 yes ago