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Thanks for the advice!!
I just got back from my first trip - only had one night to shoot - it was bitterly cold and i didn't have gloves, but still had a blast. I didn't realize how cool the architecture in Chicago was. I'm really looking forward to my next trip, when i should have more time to shoot and with the time change, the days will be be a bit longer as well.
One question i did have is regarding Buckingham Fountain. After shooting the bean, i headed down to the fountain, but it wasn't on at the time. I probably should have figured, this, since it is still winter. Do you know if the fountain will be operating mid-March
oh wow - the Conrad hotel is in an amazing location! Rush & Michigan is pretty much the nexus of the city. I would recommend walking out to Michigan Ave, then south to Millenium Park. You'll see amazing views over the river and there are lots of opportunities for street and architecture photography.
From there I'd make sure to go down to the museum campus, as that view is really not something you can miss. A water taxi from Navy Pier would be the most scenic/best way to get there IMO.
You definitely will NOT need to rent a car - you'll have the heart of the city right outside your hotel.
Edit: The Millenium Knickerbocker is a bit further North. It's still a great area, but a little further away from all of the places listed above. I would definitely stick with the Conrad for shorter trips, as you'll be right in the middle of everything.
Edit 2: I highly recommend using Google Maps Street View to plan out a walk and "see the sights" before you actually get there. Aside from photography, you'll be very close to a lot of amazing restaurants and bars - Gibson's Steak, Lou Malnati's, Merlo on Maple, and many many others. Enjoy your trips!