Welcome to Flyertalk, Arrows!

Re hotels…they are a bunch of ‘em in the Mag Mile / River North area so giving a price range and type of hotel (big chain, boutique, etc.?) would help in terms of the advice you get.

Re transport: Definitely take the train. If you’re coming from ORD, take the Blue Line – it’s the only train that runs from ORD to downtown (approx 40min). If from MDW, take the Orange line – the only train that runs from MDW to downtown (approx 30min). Which stop you get off (on either line) will depend on which hotel you choose.

Hot dogs and Ital Beefs near Mag Mile…not sure. Deep dish…only if you really like pizza. Alinea takes solo diners though it may be tough to get a res on such short notice.

Re Hancock…save the $$$ you’d spend on the observatory and spend it on a drink at the Sig Lounge (95th flr), one floor below the observatory, I think. Go around sunset – probably 5pm.

As for what else to do, if you like architecture w/some history: http://www.architecture.org/tours.

And if you're at all into art, the Art Institute is adjacent to Millenium Park (where the bean is).