I've stayed in the Hilton Chicago for over a week each of the past 3 years so it feels a bit like a "home away from home" to me by now.
The good:
It is a grand, historic hotel in a decent location (directly across from Grant Park). The staff is helpful, the rooms are relatively comfortable and the bar (Kitty O'Shea's) is an authentic Irish Pub -- brilliant! I love the blues and Buddy Guy's Legends blues club is on Wabash, across the street from the back of the hotel -- easy. There are some decent dining choices walkable from the hotel that include a good sushi restaurant and pizzeria (Lou Malnati's). Most other activities require a cab ride.
The not-so-good:
Other than Kitty O'Sheas (pub grub) the hotel's dining choices are very limited. The location is OK if you want to stroll through Grant Park or Millennium Park -- other than that you'll pretty much need a cab since the hotel is ~ 1 mile south of the river and most of the coolest places to visit in Chicago are north of the river.
The downright ugly:
Very expensive for what you get. Not sure if they hike up the rates during trade show periods (which is when I stay) but it costed $279 + taxes for a total ~ $329/night. What made the price harder to swallow was the fact that I had just stayed in The Whitehall Hotel up near the top of The Magnificent Mile (same age as Hilton but much smaller and boutique-y) in a bigger room, better restaurants, excellent staff and a MUCH better location for just over $110/night!!
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