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The Gwen
Rising Star
AC Hotel in river north
Renaissance on Wacker (with a river view of course)
Most Marriott hotels in Chicago are within a 15 minute walk of each other because they're all clustered in the loop, River North and Mag Mile. It is hard to go wrong location wise, but I'd avoid the ones in the middle of the loop proper (specifically the financial district) because there is much less activity on weekends.
Imo, pick the Springhill River North. Cheapish (150-200 a night). Modern. Free breakfast (may not matter if you're titanium or will eat in town anyway). Basically on top of the dining and nightlife in River north. Near the riverfront.
If your budget is higher (250 a night vs 150), pick the Renaissance. Amazing River views, closer to mag mile, closer to milennium park closer to loop shopping and business, but still close to River northndining and nightlife. Easier train access too.
How's the Ritz in Chicago?