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The 12 ugliest buildings in Chicago

Chicago has some of the most beautiful architecture in the world, minus these 12 ugly buildings

Photograph: Andrew Nawrocki
Visitors explored the towering Aon Center with breathtaking views downtown during Open House Chicago on Saturday, October 17, 2015.

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.

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


House of Blues, 329 N Dearborn St

House of Blues, 329 N Dearborn St

Hidden behind the iconic Marina City towers, Chicago's House of Blues looks like a tiki hut that had a giant concrete pancake dropped on top of it. The venue's acoustics lend further credence to this theory.


River City Condominiums, 800 S Wells St

We get it Bertrand Goldberg, no right angles is your thing. But most of us don't like it. After the Marina Towers, no wonder your next building was all the way down on the other side of the river. This building is a trypophobic's worst nightmare and reminds us of some post-apocolyptic pod people world.

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Greenway Self-Park, 60 W Kinzie St

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.


Marina Towers, 290 N State St

These little corn cobs are iconic Chicago architecture. But iconic doesn't mean beautiful. We love these buildings like we love an old, hobbling dog. 

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River North
Chicago Sun-Times Building, 350 N Orleans St

Chicago Sun-Times Building, 350 N Orleans St

Extra! Extra! Your daily newspaper is written in this depressing brown box with a Holiday Inn on top of it.

127 S State St

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 squares of concrete?

UIC University Hall, 601 S Morgan St

UIC University Hall, 601 S Morgan St

Really, UIC? You built a larger-than-life Triscuit cracker to house your administration. Or maybe it's more of a rogue domino. Either way, get it together University Hall. It looks like you're about to teeter over.

55 W Wacker Dr

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. 

One Prudential Plaza, 130 E Randolph St

One Prudential Plaza, 130 E Randolph St

A big gray box, skewered by a giant silver pole. Sorry, but this is the cardboard box of the sky. It couldn't be a less interesting mar on the Chicago skyline.

Thompson Center, 100 W Randolph St

Thompson Center, 100 W Randolph St

The Thompson Center was seemingly designed in anticipation of a future where everything is big and shiny. These days, it’s a glaring eyesore (literally, on a sunny day) that houses a bad food court and racks up outrageous utility bills.


Aon Center, 200 E Randolph St

This is the second-tallest building in Chicago, and that's all it has going for it. This simple, plain building wasn't even built correctly. Chicago has some of the harshest winters, so using marble for the exterior was not a good call. The entire building had to be resurfaced with granite (costing more than $80 million) because chunks of marble were cracking off and falling onto the streets. Ouch.

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Ashland T

This is not only a pathetic attempt at online journalism but the absolute worst & most inacurrate list ever. Was this written by a three year old? FAIL.

Carl M

While some of these buildings are truly ugly, some here are not, your architectural criticism here needs to be rechecked. You get a C-

Koji B

It seems everyone has criticized the similar options that I disagree with on this list, so I'll just add one no one mentioned - 155/151 N Michigan! The newly renovated retail floors on the base level completely screwed up the look of the entire building, not that it was anything great to begin with (is that a classic "rust" iron look??) but the overly modern base really emphasizes how old and terrible the rest of the building look.

michael j

Two things for critics to remember:

a.  "ugly" isn't the same as "not beautiful"

b.  buildings exist for what's inside; how well does the building serve?

You didn't demonstrate that you have a standard by which to judge a building.  Your comments suggest "ugly=don't like".  

The Sears Tower is not beautiful.  It is unadorned.  Ugly?  No.  

Rupanshi D

I'm not going to comment on the architecture you've chosen to criticize today, I'm just going to say: If you're doing something, at least do it right.... you forgot the ugliest of them all: The Marina Towers!  

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

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

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

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

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

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

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

@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

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

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

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

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

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

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


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

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

Scott K

@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.


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

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

William G

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