Heard enough about Chicago’s oh so lovely architecture? May we suggest a walk with the Ugly Buildings Tour

A Wendella tour boat glides past Mike McMains on a rainy Friday afternoon in October. The tour guide is saying something about the remarkable riverfront and the majestic Merchandise Mart, and though it’s all a little too faint to hear clearly, it’s probably positive, upbeat stuff, right? Of course, it is. Chicago, oh beautiful Chicago, has great architecture, look at this beautiful building, look at that beautiful building, this was made in such-and-such architectural style by genius so-and-so, blah blah blah. A moment later, as the boat passes from sight, McMains gathers his own architecture tour around him, a walking tour, of a dozen people today, a handful from out of town but many local.

Welcome, he says, to the Ugly Buildings Tour.

He begins with a question: What, in your opinion, is the ugliest building in Chicago? His eyes widen, anticipating the replies. Don’t be shy, is his implication. Not that anyone is.

The group goes in the circle, enthusiastically airing annoyances and peeves. A few bring up architectural flubs in their own far-flung hometowns, but when time comes to roast Chicago, Chicagoans, a typically cheerleading bunch, unleash. Thompson Center. Soldier Field. Someone hates “big cinder block buildings with six different materials on the facade.” Someone else hates squat, brown 55 West Wacker. Brutalism, in general — who needs it! Someone loathes Marina City. McMains has heard it all. He does not look aghast: Since creating the Ugly Buildings tour in August, participants have complained about the Aon Center, the Crain Communications Building, that seemingly-windowless eyesore the Metropolitan Correctional Center, that “Big Red” blemish at 333 S. Wabash.

McMains nods and nods and nods.

The Ugly Buildings tour of Chicago is the local architecture tour that needed to happen. Chicago needed taking down a notch. Too much civic pride! What is this, Des Moines?

McMains, 43, a Minnesota native who moved here in 2000, had been a 15-year veteran docent of the Chicago Architecture Foundation; he also worked in real estate investment management and at the height of the pandemic, when his position was relocated to San Francisco, he decided to stay in Chicago and follow his passion, which was developing architecture tours. So he launched Tours With Mike, starting mildly, with a greatest-hits architecture tour, a riverfront tour but then, a tour of disgusting buildings — right now, he mainly covers lousy architecture on the riverfront, around River North, in Streeterville, but it’s been so successful, he’s expanding to a Loop edition of Ugly Buildings in spring.

When you’re in a bad mood, possibilities are endless.

The day I attended the tour he started with disclaimers: He will make fun of Donald Trump and use a curse word during the discussion of Trump Tower but he assures, it is warranted. (Indeed, when buying tickets, the form asks you to check a box to ensure you’re OK with this.) He explains that he will discuss two kinds of ugly: “The ugliness that you see, which can be a disorganized facade, aspects that don’t feel thought out, etc. And the other type of ugliness is ugliness you feel — buildings that don’t seem to welcome human beings, spaces that do not engage people.” Having said that, he also does not want anyone to worry about whether they personally think a structure is ugly. “Ours is a safe space — just because something is ugly doesn’t mean you can’t like it.”

And with that, we walk.

Our first stop is 350 N. Orleans, also known as the Apparel Center. From where we stand alongside Merchandise Mart, looking north, it shows no untoward distinction, no aggressively obvious repulsiveness. But it is, McMains notes, “aggressively bland.” Which is fair. He continues: “This was designed by Skidmore, Owings & Merrill and finished in 1977, and you will hear a lot about this firm on this tour, not because they are a bad firm. but because they are a very big firm. They designed the Hancock Center, Sears Tower, — they designed some of my favorite buildings. But this right here, this is not one of them.” Among his complaints, lack of cohesion between the two parts of the Apparel Center. “When I look at these two towers I see a conversation between good friends, the one on the left is a mess and drawing a lot of attention, the one on the right is embarrassed and asking, ‘OK, why are you like this?’”

Before moving on he pauses:

“Am I being too harsh?”

He reads the faces of the group. Sees only smiles. OK, onward.

We pass the Merchandise Mart Hall of Fame and its pedestal busts of Montgomery Ward and Marshall Field. He compares it to a trophy hunt. He stops at the apartment complex EnV Chicago on Kinzie: “They spell this place ‘EnV’ because they’re edgy.”

A tourist whispers, “I wonder what he’s going to dump on next?’

Indeed, you do wonder, not because of the quips, but the insights, the thoughts, good and bad — you wonder why there aren’t more architecture tours with a touch of opinion.

McMains also wondered. Sort of. Though he takes pains to say he loves the Chicago Architecture Foundation, he told me later he knew a critical eye was not welcome on its tours, so as a docent, he never bothered to suggest an Ugly Buildings tour. “Bad architecture is a sensitive topic,” he said. “It’s a balance. Chicago loves its architecture and loves showcasing it to the world and tourists, but then you don’t see anyone talking about all of these other buildings we have, and if everything you’re seeing is great and beautiful, you need to know the ugly to understand the beautiful. It’s teaching people to look more critically. But it’s also challenging. You want to be funny without being mean.”

McMains has blue eyes and wears a blue polo, he’s very polite, comes off like a youth pastor and seems careful not to offend. But he does not disguise the cringe in his voice.

He notes the use of computer-aided design to craft irregular forms, but also, “the use of computer-aided design to make irregular forms just because.” We stop at parking garages, though before you can wonder who expects a parking garage to be pleasant to look at, McMains has you wondering, Well, wait, why can’t they be pleasant to look at?

“OK,” he says, turning to River North, “now I’m going to talk about sad little balconies.”

Soon I hear hushed comments among the group:

“Disgusting.”

“Embarrassing.”

“Aggressively horizontal.”

“A vision in beige.”

At one point we pause beside an aging, original River North building amid new construction. A woman from out of town asks if the old brick facade we’re standing beside, if the city will “do anything about this.” A woman from Rogers Park gasps, “No! Do not touch that!”

The stakes feel a little higher when you’re not automatically in awe.

At the riverfront, McMains discusses contextualization and architecture, how buildings play off each other, appear to compliment or call out neighbors. Postmodernism references styles of the past, often in a whimsical manner, he explains, but 77 West Wacker, by Spanish architect Ricardo Bofill, references classical revival without being clear “what it’s trying to communicate. Those white stripes — it’s a straitjacket. Which might be appropriate for a building like this that thinks it’s playing off of Ancient Greece.” He points to a building next door that nicely incorporates some of the problems he’s noting. Then points once more to 55 West Wacker, next door. “I see this as a Danny DeVito, shorter, stocky, but not without its charms. It’s ugly but it also makes me happy.”

It’s a distinction he makes thoughtfully.

He calls the 1895 building that holds Harry Caray’s Italian Steakhouse on Kinzie — an ornate, brick antique in a Dutch Renaissance Revival style — “continuously ugly for 125 years.” But at Marina City, he likes it, and notes “that doesn’t mean there isn’t plenty to critique.” The driveway is “quite aggressive,” some of the sidewalks seem difficult if you operate a wheelchair, but in general, “here’s ugliness you feel — it’s like if you don’t live here, they don’t want you here.” And the House of Blues — what’s up with that dumb roof? “You’d think lumpy uncooked breadsticks were an odd choice for trim, but oh well.”

He notes the enormous genitals on a statue of a bull outside a steakhouse.

“Why point this out? An artist designed it. Here’s the result. Please think about that.”

At Trump Tower ... he notes many of the positive elements. But also, that the retail space along the river is empty. Probably now because of associations with Donald Trump, he said, but also, probably because those retail spaces are awkward, recessed, sunken — not welcoming.

He moves through Pioneer Court on Michigan Avenue, noting its gorgeous mise en scene, promising “to talk ugly things in Chicago soon.” Which he does, a moment later.

We stop at Ogden Plaza, at the corner of Columbus and Illinois.

“This is a public park,” he says, arms outstretched before a large patch of concrete. “There’s some green space but the benches are stone and hard, so don’t overstay your welcome! It’s very isolated from street level and feels unsafe and unpleasant, and see this” — he notes a cylinder in the center of the plaza — “this was art! It was titled ‘Floor Clock II’ and made by Italian artist Vito Acconci though the hands of the clock haven’t been a part of it for a long time. Still, you could make a park here that people engaged with, if you included unusual elements such as grass! OK, what’s everyone feeling?”

Sad, someone says.

Missed opportunity, someone says.

Like when you visit a city for the first time, someone else says, “and they show you around and you’re like, well, now that I see it clearly, a lot of this place totally sucks.”

McMains smiles and shrugs and nods in a noncommittal way. “One thing I know, people wouldn’t come into this park at all. Unless some tour guide dragged them in.”

cborrelli@chicagotribune.com