Terrific, if you can get a good upgrade
The W Lakeshore is an interesting property. I'm rating this based on my experience, and not what I think the standard experience is. When checking in, due to our platinum status, and the fact that my wife and I were celebrating our anniversary, we were upgraded to a marvelous suite facing the lake. The view was terrific, and the suite was beautiful and spacious. It did look a little loved and worn in places We had a powder room off the main entrance, a spacious living room with wetbar, and big windows looking over the lake. The location is terrific, across from Navy Pier. And 5 miuntes to Michigan Avenue. 
When I was looking at the floorplans, the standard rooms looked fairly small -- and the bathrooms very small. But our suite had quite a large bathroom with separate shower, which was quite nice and spacious. With a view all the way out the window to the lake, no less!
It's clear that this hotel was something much more standard, that the W shined up. The lobby is a neat place. A standard hotel lobby during the day, turned bar and meeting space in teh evening. We also had drinks on the rooftop bar, which was sleepy (mid week), but a good view and comfortable atmosphere. 
The complimentary Acura Car Service was terrific -- we took it out to Wrigley Field for the Cubs Game. I just wish they came to get you, but, alas, it's only one-way service. 
We had a nice breakfast in the lobby the next morning, and it was mostly filled with young businessmen. I think the hotel loosens up on the weekends, and I'd like to see that sometime.
The only hiccough for us on this trip was when we called the bellman they never showed up. Oh well, we can grab our own bags. 
Overall, I enjoyed this hotel very much and I am rating it on the experience that we had (upgrade to a great suite, late check-out, comped breakfast, and a terrific low corporate rate). Had I paid the $400+ they were asking and didn't receive any upgrades, I would think that this place is terrible value. That said, I really like W Hotels, and this one -- while certainly no Montreal -- is a nice place. I'll come back on a Summer Weekend next time.