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The Drake? I wouldn't stay there. Bedbug city. If you wanna stay in a hotel, check out the Hotel Burham. It's a boutique hotel run by Starwood I think. It's got fantastic architecture and a top notch restaurant attached.
Also I'd check out VacationRentals.com and see what's available. You can find nice condos downtown for the same price or less than a hotel.
The Architectural Riverboat tour is something I'd recommend. Bring a jacket, it can get pretty cold on the water even in late May.
Also I'd suggest visiting the Chicago Botanical Garden. You can get there by taking the Metra train from downtown, and there's a free shuttle from the Metra stop to the Garden. Plus it's free of charge unless you drive a car there, then parking is $20.
For restaurants, I don't know what your tastes are but for steak I'd recommend Fogo de Chao if you want something lively, or one of our famed chophouses like Kinzie Chophouse or Chicago Chophouse. If you like excellent beer and pork try The Publican. It's an upscale European style pub. Very crowded but lots of fun.
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