Chicago architects dish on their most, least favorite buildings

FitzGerald prez, Hartshorne Plunkard founder and others discuss what they like and dislike

Rachel Herzog

Sep 24, 2023, 7:00 AM

In a city so frequently lauded for its architecture, what makes any one building the favorite — or least favorite — of someone who practices the trade?

For some of Greater Chicago’s top architects, it comes down to the way the structures mirror their surroundings — for instance, the way Lake Point Tower echoes the bend of the Chicago River, or the plantlike waves of the St. Regis Chicago — or don’t contribute to them, like a windowless parking garage.

There’s also the balance of making a building stand out in the skyline without doing too much.

“Good architecture has a consistency to it that holds the building together,” said Mike De Rouin, president of FitzGerald. “For us, it really comes back to what is the singular idea that holds this building together and how do you reinforce this idea without diluting it?”

De Rouin, along with three other Chicago-area architects, chatted with The Real Deal about what they believe are the best and worst buildings the Windy City has to offer.

Mike De Rouin, president of FitzGerald

Favorite Buildings

Reliance Building, 1 West Washington Street

“There’s a lot of exploration of what is a high rise and how can you put in big windows and how do you build with a steel frame?… It’s an early example of a skyscraper.”

Lake Point Tower, 505 North Lake Shore Drive

“It’s such an iconic location and they built a community there before there really was one.”

“They did sort of a masterful job of being able to create a place for the people that live there and give them a really iconic location for people to envy, in some ways.”

“It’s really nice because the form is allowed to exist and share itself, similar to the way that 333 Wacker does as it bends around the river, responds to the environment that it’s in and doesn’t just get lost in ornament and lets the form be what everybody absorbs rather than an ornament. That’s what’s best about the entire structure.”

“It stands on its own. It’s really quite timeless.”

(Style) The Chicago Bungalow

“It’s an iconic house type that is scattered across the city mostly built in the teens and ’20s into the ’30s. I’ve lived in two of them. They live really well, they can grow and modify with families, they can sort of stand the test of time. They’re a really iconic housing type for Chicago and they come in every brick color and every roof color and some are one and a half stories and some are only one story, some of them just march down the block one right after the other.”

“They just really have a great feel, a great place to be.”

Least Favorite Buildings

Harold Washington Library Center, 400 South State Street

“It has this nice singularity but it’s almost a joke of itself because the ornament is just so intense that, yes, it drew on a lot of Chicago examples, but it also drew on a great French library as an example. … It’s just too much.”

77 West Wacker Drive

“It’s sort of the prime example of postmodernism taken to a skyscraper. … Some friends have called it a Parthenon on a stick. … It’s trying to take a classic architectural style and put it on sort of the wrong building typology.”

Jim Plunkard, co-founder of Hartshorne Plunkard Architecture

Favorite Buildings

The John Hancock Center, 875 North Michigan Avenue

“It’s unique and it’s iconic and it’s so ‘big shoulder Chicago,’ so for me, that’s unmistakable on our skyline and any shot you see of our city. I always admired that when I moved here in 1981 until now, I appreciate it even more.”

Chicago Athletic Association Hotel, 12 South Michigan Avenue

“I don’t love it because we did it … you have this building that was preserved up until they closed in 2007. And now it’s so accessible, this history is so accessible to people.”

“This was such a treat. I felt like a kind in a candy shop working on that. I think we were just good stewards of that building.”

Tree Studios, 4 East Ohio Street

“I love the complexity of it. It’s a mixed-use development connected to the [Medinah Temple] and has a beautiful courtyard and people live there. It’s everything you want in an urban, central location where it’s so walkable, there’s a shop every 25 feet and that in and of itself kind of curates a very interesting brand of tenants. I’ll sit outside at the cafe over at Osteria Via Stato and can just imagine a horse and buggy pulling up. … It’s adapted well to history.”

“It’s a hidden jewel. It kind of flies under the radar, everybody’s radar.”

Least Favorite Buildings

350 North Orleans Street

“It is just a big beast. It’s got this massive brick, unadorned base. … It’s just a big block and then there’s five stories that sit on top of that.”

“It has such a lack of character that it becomes a background building.”

“It’s just, to me, a site that just embodies ugly. No character.”

60 East Lake Street

“I was part of it and I remember drawing it and I remember detailing it, and the fact that it’s still around and hasn’t been reskinned is amazing.”

401 North State Street

“It has no windows and it’s lifeless.”

“I just imagine whoever drew it never visited the site and never really loved the city.”

Nathan Kipnis, founder of Kipnis Architecture + Planning

Favorite Buildings

The St. Regis Chicago, 401 East Wacker Drive

“That St. Regis is really cool because it’s very organic, it looks like these things are just kind of weaving up into the sky at different levels.”

“A shapely, sensual thing, but not a ridiculous penis.”

“It’s very striking on the skyline and that’s a big deal in Chicago.”

The Tribune Tower, 435 North Michigan Avenue

“I would say the Tribune Tower renovation is unbelievable.”

“What a great history that building has.”

Baha’i House of Worship, 100 Linden Avenue in Wilmette

“It’s one per continent and I’ve seen two others and this one is the nicest one. I bike ride by it up Sheridan Road and it’s a landmark but to go inside of that thing and see a tracery of stone on the ceiling and on the outside and there’s glass in the middle of that, I don’t even know how they did that.”