I just wrapped up a stay at the JW Marriott Grande Lakes in Orlando this morning to finish up the 75 nights I needed for platinum status for 2013. Thinking of heading to Chicago over the holidays when visiting some family in the area. Anyone have any good experiences with getting upgrades as a Platinum in the windy city?
You might know that Chicago is a "convention city", particularly with through-the-year trade shows at McCormick Place (SE of city) and at the Rosemont (near O'Hare), so getting upgrades during these times might be more difficult. Any hotel downtown, especially along North Michigan Ave. , will generally be expensive, regardless of time of year. Even while attending trade shows downtown, I've often stayed outside the city in Lombard, Oakbrook (West of I-294), Woodale, Rosemont and Des Plaines (NE of city) and drive into the city parking at McCormick Place. You have to negotiate the in-outbound traffic on Kennedy and Eisenhower Freeways during peak times, so anticipate up to one hour commute, however.
If you like Italian food, my all-time favorite is Tuscany, 1014 West Taylor in Little Italy, SW of the city. If you're driving it's easy to get there from downtown, or you can take a taxi.