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When I lived in Chicago, from 1984 to 2001, the Hancock's observation deck seemed to be a better overall experience than the one at the former Sears Tower. The Hancock is closer to the shoreline and it's situated in a much more touristy part of the city than the Sears Tower. I used to live not too far from the Sears Tower, and I like that part of the Loop just fine, but it wasn't really a tourist destination.
For a one-day trip, I'd recommend that you take a boat tour (if you have warm clothes with you). The ChicagoLine tour is highly recommended and is still offering tours (before Winter sets in). The Wendella tour is also a safe bet--they've been in business for a long time. You can see a lot of the city from the water and then be near the Magnificent Mile where you can walk to other prime spots in the Loop (i.e. the Art Institute) and/or the Near North Side.
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