The 15 ugliest buildings in downtown Chicago

We're ready to erase these architectural misfires from our city's skyline

1/15
Photograph: Monsurat Yusuf
Greenway Self-Park, 60 W Kinzie St
2/15
Photograph: Martha Williams

214 S State St, a.k.a. Roberto’s Building

3/15
Photograph: Monsurat Yusuf

137 S State St

4/15
Photograph: Monsurat Yusuf
127 S State St
5/15
Photograph: xmoddyx

The Museum of Contemporary Art, 220 E Chicago Ave

6/15
Photograph: vxla

Ontario Place, 10 E Ontario St

7/15
Photograph: Lorenia de la Vega

Willis Tower, 233 S Wacker Dr

8/15
Photograph: Bo Nash

55 W Wacker Dr

9/15
Photograph: Adam Fagen
One Prudential Plaza, 130 E Randolph St
10/15
Photograph: Daniel X. O’Neil

Harold Washington Library, 400 S State St

11/15
Photograph: Monsurat Yusuf
10 S LaSalle St
12/15
Photograph: Chicagogear

311 S Wacker Dr, a.k.a. the White Castle Building

13/15
Photograph: Josh Michael G. Belarmino

House of Blues, 329 N Dearborn St

14/15
Photograph: Peter J. Markham

Chicago Sun-Times Building, 350 N Orleans St

15/15
Photograph: Terence Faircloth

Thompson Center, 100 W Randolph St

Chicago is known for its diverse and magnificent architecture, from the neo-Gothic facade of the Tribune Tower to the modernist waves that grace the Aqua Tower. In the summer, our streets and waterways are clogged with buses and boats on architectural tours. But even a skyline as gorgeous as ours has a few duds.

Inspired by a certain real estate mogul who is slowly but surely slapping his name on the side of his ostentatious skyscraper, we assessed the city's downtown buildings and assembled a list of some of the least aesthetically pleasing buildings in River North and the Loop. Got a few you'd like to see added to the list? Leave a comment below.

RECOMMENDED: The 50 most beautiful buildings in Chicago


Greenway Self-Park, 60 W Kinzie St

You are a lowly parking garage in River North. Don’t pretend you’re the damn Pompidou Center in Paris. You embarrass yourself.

214 S State St, a.k.a. Roberto’s Building

We at Time Out are lucky enough to work near this architectural wonder, so we get to gaze upon it every day. It was far uglier when it was occupied by the men’s store Roberto’s, due to its gigantic sign featuring men in suits, painted by an artist of dubious talent. Now all that’s left are four stories of shit-brown concrete and a clock.

CVS, 137 S State St

On any given day, this windowless cube belches fat plumes of… steam? smoke? dragon farts? What vague machinery lies above the drug store in this cyberpunk block? Ridley Scott should take note in case he needs a laundromat in the Blade Runner sequel.

127 S State St

The saddest part about this building, built in the late 1910s, is that you can see, at the very top, that it was once inoffensive. Then some dimwits had the idea to update it with slapped-on features. Behold the section with the white siding and windows with shutters, making it look like a Gold Rush saloon. And above that...what is that, even? White square of concrete?

The Museum of Contemporary Art, 220 E Chicago Ave

Don’t get us wrong—we love what’s inside the MCA, but that sad, mostly windowless gray box does the museum an injustice.

Ontario Place, 10 E Ontario St

With its rows of porches and oddly arranged windows, Ontario Place could be mistaken for a slummy high-rise from District 9. Not the kind of “private residence” we would want to spend a couple thousand dollars each month to live in.

Willis Tower, 233 S Wacker Dr

A controversial choice for sure, but let’s be real: The only things Willis Tower has going for it are its height (now the second-tallest in the Western Hemisphere, thanks to New York’s One World Trade Center) and the Ledge (enjoy at your own risk). It’s just a collection of hulking black boxes topped with walrus tusks.

55 W Wacker Dr

An otherwise impressive stretch of riverfront architecture is marred by this molded concrete tic-tac-toe board, adorned with tacky fonts. Is it any surprise that Chicago’s Fox News bureau calls this building home?

One Prudential Plaza, 130 E Randolph St

A big gray box, skewered by a giant silver pole. This is some Eastern bloc shit.

Harold Washington Library, 400 S State St

The downtown public library is a subject of debate in our office: Are the clashing architectural styles an inspired combination or a muddled mess? Are the bright green aluminum sculptures that line its roof artful or tasteless? Probably the latter.

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Comments

22 comments
Mark S
Mark S

Sounds like the next Chicago Time Out article should be "15 Time Out editors who should be given the pink slip." Ugly is the SUV that drove you into Chicago from Iowa or Ohio or wherever y'all learned to read.

Chris C
Chris C

You guys nailed it. Thank you! What a relief to hear someone outside my own head wishing these buildings were replaced! The library, those multi-facade buildings on state street, 55 west wacker and 311 s. wacker are all ugly, the thompson center should have been used in 'total recall' and the house of blues makes me think of a whale. Also I really wish they'd at least paint the cook county admin building white or grey. A yellow high rise looming over Daley Plaza is no fun.

d s
d s

The author of this list definitely needs a class or two on design!

w G
w G

Wow - you have some odd choices which indicates your taste - not necessarily the truth.  One or two of these are - yes - unappealing.  The majority of them are just part of the eclectic beauty of the city. Loosen up.  Who made YOU architectural critics????

Krista J
Krista J

The library is hardly ugly. It is genius design in that it looks old and respects its surroundings, unlike some hideous metal thing that sticks out like a sore thumb in the center of downtown, especially with Chicago being so notable architecture-wise. 


And while the Sears Tower (it's the Sears Tower regardless of what the Willis people think) is not my idea of beautiful, it's pretty iconic and to say it's ugly is rather stupid. Especially if you are from Chicago. 

Mark S
Mark S

The library does not look old and it does no respect to Harold Washington's legacy nor the surroundings. And the interior is about as useless as you'll find in a library. It's like they spent their budget on those misproportioned gargoyles.

BUT, that doesn't mean it should be torn down.

Andrew W
Andrew W

Ok. This is outrageous! I think I can speak for everyone when I say this is the most illogical, insane, and pathetic attempt to criticize anything ever created!


Now some of these buildings I definatley agree with (55 W Wacker), but going out and saying the Sears Tower is ugly, is going to get you jumped. Buddy you must be from New York or Boston, because no true Chicagoan would even imagine saying the Sears Tower  is "just a collection of hulking black boxes topped with walrus tusks". What is that?!?!?


I guess next you'll say the 'X's on the Hancock make it look fat!


I am appalled! The Thompson Center is also an incredible engineering feat! It's incredible to look at!


311 S Wacker is also a stunning building to look at. It is one of the finest buildings in the Loop.


I do not know where you came up with this, but why don't you go back to Queens!

Gabe L
Gabe L

@Andrew W - I guess it just goes to show that taste is relative. I happen to like 55 W Wacker - an example of "soft" Brutalism. As well, the skyscrapers on either side were developed with horizontal facades that recognize the height of 55 W.

It is what it is.

Joan W
Joan W

I hope the author will go on a Chicago Architecture Foundation tour so he can learn why some of these buildings are architecturally important (e.g. Prudential I, first "skyscraper" built after WWII in Chicago);  and how they "make sense", architecturally and aesthetically  (e.g. 311 S. Wacker Drive --  as a contrast to its more well-known neighbor, Sears/Willis Tower,  or the HLW Library even).


Perhaps then, the "attractiveness" of the buildings will become more apparent.


I am a member of CAF and I'd be happy to take the author on one of CAF's walking tours, for free, anytime.

Clint B
Clint B

remember #1 is a parking garage - for a parking garage its great- those are wind turbines- I don't know if they work but if they did and actually powered something- this would be the coolest garage in the city.

Julie B
Julie B

This is the first time I've commented on anything written on TimeOut, but felt I had to here:  This just seems to be so random and nonsensical.  Many of the buildings listed here are some of the most beautiful and interesting in Chicago.  Just because they are not new and sleek doesn't make them ugly, they give the city character, beauty and a uniqueness all its own. 

Michael K
Michael K

The MCA?! Are you insane or simply blind? That's one of my favorite buildings in the city. Have you ever seen the new Trump monstrosity? Why isn't THAT p.o.s. atop the list?

Michael C
Michael C

Would you let a theater critic write about the stock market? This is truly embarrassing. Maybe half of these are questionable. The standard seems to be "weird is bad." Ugh. embarrassing 

Englewood R
Englewood R

UIC's University Hall.  What an eye soar that could be seen from major Interstate Highways.

AnneRossley
AnneRossley

There's "dated" icons (House of Blues, Willis/Sears Tower) and then there are just "non-starters, such as the CVS...  I'll take a "dated" icon over a nonstarter any day - that's what makes our city so unique!

Jennifer S
Jennifer S

Must have been a very slow news day for you Time Out Chicago.. Write about more important things going on! 

EdgewaterScott
EdgewaterScott

@traceybee I think it's as slapped together as some of the buildings are. I stopped reading when I saw the Harold Washington Library Center. One of my favorite buildings.

tombellino
tombellino

Absolutely no sense of history or design. A few of these are legitimately bad, but most of them are excellent examples of architecture throughout the decades. Chicagoans are so lucky to have so many pieces from virtually every modern building style. 

Frank S
Frank S

I miss when TimeOut Chicago did ACTUAL research and journalism instead of whatever this opinion piece is supposed to be!

William G
William G

I guess this is why I don't read architecture blogs for opinions on restaurants and brewpubs.