Kevin / October 13, 2009 4:04 PM

Trump Tower. Boring.

Peebo / October 13, 2009 4:05 PM

Harold Washington is in my top five, but the ugliest one downtown is that concrete monstrosity south of the Daley Plaza, across the street.

J / October 13, 2009 4:14 PM

Aside from the building I work in on the northwest side, I'd say 55 W Wacker.

Luke / October 13, 2009 4:22 PM

I can think of a lot of ugly buildings, but no hesitation about the ugliest: that Advocate hospital (whatever it's called) at Division & Leavitt.

Dmitry Samarov / October 13, 2009 4:55 PM

The CNA Building at 333 S.Wabash always filled the 'what's wrong with this picture' part of the Chicago skyline.

Y A J / October 13, 2009 5:25 PM

The Thompson Center tops my ugly list and I'm stuck working here.

I agree with everyone so far except the hospital, which is a Brutalist architecture ideal, thus deliberately ugly, so I can't count it.

Monica / October 13, 2009 5:34 PM

The building you enter to get to the Orange-Blue-Green-Pink-Brown Lines at Clark.

Jason / October 13, 2009 6:21 PM

Soldier Field is the worst architectural tragedy, by far.
As for office buildings, I agree with CNA. Architect shoulda refused to paint it anything other than black.

PMan / October 14, 2009 12:01 AM

I think there's a 4+1 in Edgewater or and apartment building in the Harlem/Foster area that would take the cake. In downtown, I agree Peebo and Jay. I also think that the building that now houses the Sun-Times is really wretched.

David / October 14, 2009 12:23 AM

A good number of the buildings on the east side of Sheridan (north of Lake Shore Drive) are definitely on the list for me. Other than those, pretty much every CMU condo building in the city counts -- especially this king of all CMU structures.

Robyn / October 14, 2009 12:31 AM

Some of the City's Ugliest buildings:

The former highrise Montgomery Ward HQ that's @ Chicago/Larrabee. So ugly. (not the bldgs that abut the river on either side of chicago)

The building that now houses the Chicago Sun Times.

University Hall @ UIC (the lone high-rise on campus, 601 S. Morgan)

maardvark / October 14, 2009 7:02 AM

The question is too easy, since there are so many hundreds of buildings in town that are architecturally boring or otherwise fail. For example, just about every residential high-rise in River North.

So instead, how about my least favorite building that everyone else likes. In that category, I'm going to cite the Equitable. I know it was one of the earliest black-box skyscrapers, but it is NOT one of the most elegant.

Honorable mention in this category goes to the Water Tower; not because I don't like it, but because I want to quote Oscar Wilde's comment about it ("a castellated monstrosity with pepperboxes stuck all over it").

Mike / October 14, 2009 10:00 AM

For example, just about every residential high-rise in River North.

Indeed. I love how they're all resting on poured concrete parking lot podiums.

Andrew / October 14, 2009 11:32 AM

Wow, not only is the Thompson Center ugly, it's dangerous!

Lester / October 14, 2009 11:43 AM

Formerly known as the Doral Building, this thing is a real eyesore spoiling the background of the Pritzker Pavillion.

Mucky Fingers / October 14, 2009 12:11 PM

Yes, the CNA building unpleasantly stands out amongst the downtown Chicago skyline.

Guy Smiley / October 14, 2009 12:14 PM

Keeping it on an out-of-the-way level, this building in my Edgewater neighborhood is pretty funky.

Winthrop Building

annie / October 14, 2009 12:49 PM

This one!

annie / October 14, 2009 1:24 PM

I meant 7801 S. Cottage Grove.

ewr / October 14, 2009 2:27 PM

I've always thought Louis Farrakhan's house was ugly, but not just for the architecture

Jane / October 14, 2009 4:13 PM

Kevin, I disagree, have you seen it in the am with the reflecting of the sun off the lake - it is sublime and very well thought out. I think Corn Cob Towers are pretty ugly myself, all the while a tip of the hat to that architecutral style.

David / October 14, 2009 4:31 PM

Whichever building the Mayor happens to be in right now.

Stillman / October 14, 2009 5:01 PM

Consider, briefly if possible, the 311 S. Wacker building, with its overilluminated corona and gaudy palm trees in the lobby.

Matt / October 14, 2009 10:36 PM

My vote for ugliest is Ontario Place, that awkward black glass thing at Ontario & State.