Neglected property, same bad W design
I'll start by admitting that I've never been a fan of the W brand design that favors pretention over practicality. I travel for business and, consequently, have had to stay in several W properties and they've all suffered from the bad design decisions. The W Chicago Lakeshore is no exception and the poor experience is compounded by bad property management. I stayed in a "wonderful" room for 5 nights to attend a conference. Some of the lowlights:
*Nickel-and-diming is in effect here. In-room internet is $15.95 a day, I was told parking is $55 a night, a room with a lake view is $50 extra a night. They give one bottle of generic brand water in the room and then scatter around the expensive Fuji bottles. I never touched the mini-bar or other snacks, so I can't comment on their prices.
*The awful shower design persists: Shower has no lip to contain water and only a half glass "door" to keep the water in. Therefore it floods all over the slate bathroom floor. I nearly slipped twice--I can't help but wonder if they haven't been sued over bathroom falls. If you use the bathmat to sop it up, you then have no dry bathmat to stand on. The "rain" showerhead does not adjust in any way. There are no towel racks in the bathroom at all--just a couple of hooks. Also, as another reviewer commented, the half door in the shower means nothing traps in the shower heat so if you're cold sensitive, it's quite uncomfortable.
*Lighting in the bathroom is poor. This location provided a dimly lighted makeup mirror but it's installed too low and doesn't adjust up or down. Enough people have tried to adjust it that the screws have stripped and it's about to fall off the wall. 
*The shuttered window from the bathroom and the woven bathroom door are ridiculous. It's okay for a solo traveler I guess, and does afford one the ability to see the TV from inside the bathroom while doing makeup and hair. But I cannot imagine staying in that room with another person. There is simply no bathroom privacy, even with the window shut. No one should have to be that intimate with another person. 
*In room air conditioner is horrible. The thermostat read 74 the whole time I was there, no matter how hot or freezing it was. And those are the two options you get. The room is too small for such a concentrated flow of chilled air so if the unit is on, you freeze. If it's off, you roast.
*Room smells like old dirt and mold, covered up by a nasty, super-sweet air freshener that gave me a headache my first night. In fact the entire hotel is filthy. One example of pretention over practicality is the mats in the elevators, surely meant to cover up the disgustingly gross elevator carpet. They have mats that say good morning, good afternoon, and good evening, so they take the trouble to change them out three times a day. However, they just fling the heavy mats into the elevators and don't straighten out the bulges or make sure they cover the dirty floor. More than once, I saw someone trip on the bulge in the mat. 
*Another example of pretention over practicality: fancy fruit flavored water in the conference rooms. No glasses to drink it with. They just don't get the concept of how things function. It's all about how things look.
*Walls are paper thin. You hear everything in the hall (including late night drunk meanderings) and in the rooms next to you. 
*Room service food is okay if you like airplane food. I arrived late the first night so ordered dinner. BTW, there is no menu in the room. You have to wander through a complicated set of menus on the TV to find room service menus. Stupid. Anyway, rubber chicken and everything that came with it swimming in oil. Gross.
The few positives: Every time I had to interact with staff, they were very nice. I was offered an option to use the "green" program--no housekeeping at all in exchange for 500 extra Starwood points per night. I haven't confirmed that I got the extra points yet. I did it chiefly so housekeeping wouldn't come in and spray the air freshener every day. After three nights I needed new towels (no racks to dry them, remember?) so I called and asked for housekeeping to come in. I left a note (with a tip) asking them not to spray the air freshener. The housekeepers did exactly as I hoped. Also, the lakeshore location is nice for walking at the beginning and end of each day. And there are several coffee shops and nice places to eat nearby so you can easily avoid the bad hotel food. The bed was comfortable.