Museums

• The Museum of the Art Institute of Chicago
• The Museum of Contemporary Art -- this museum is good or bad depending on what the current show is. If the current shows sound interesting to you then it's great... otherwise, not so much.
• The John G. Shedd Aquarium
• The Museum of Science and Industry
• The Field Museum

Views

• The Sears Tower Skydeck
• The Hancock Observatory in the John Hancock Center, 875 N. Michigan Avenue, in the Magnificent Mile shopping area. Considered by many to be a better deal than the Sears Tower Skydeck (cheaper, a shorter wait, and in a shopping area, but not quite as high).
• The bar and lounge in the Hancock building. Free to enter, and just one floor below the Observatory. You get the same view, and spend your money on a drink and a nice atmosphere instead of an entrance fee.

Tours

• CAF Architecture river cruise -- this might be cold at this time of year, but it's an excellent tour.
• Other Chicago Architecture Foundation Tours -- they run several other tours every day as well.
• Frank Lloyd Wright Tours -- in Oak Park, the suburb immediately west of Chicago where Frank Lloyd Wright built a great number of homes. Many (most?) of them are still occupied, so you mostly see the exterior of the buildings.

Travel Guides for Chicago

• Fodor's Guide to Chicago
• The Lonely Planet Guide to Chicago
• WikiTravel Chicago

Shopping

See Shopping in Chicago.

Restaurants

If you're going to shop, you've got to eat - see Chicago Restaurants.

Bars

Because, well... because. See Chicago Bars.

Package Deals

If you are going to tack on some real vacation time, these can save you a few bucks.

• CityPass ($49.50 adults, $39 children) includes the Shedd Aquarium VIP, The Field Museum & Underground Adventure, Adler Planetarium, Museum of Science and Industry plus OMNIMAX, and The Hancock Observatory

Neighborhoods

On the Blue Line, before you get to the Loop (aka Downtown), there are two interesting neighborhoods you might want to explore.

The first is Wicker Park (and immediately to the north, Bucktown). The Damen stop is at the center of Wicker Park. There are interesting things southeast on Milwaukee (to the Milwaukee stop), or north on Damen (which takes you towards Bucktown). Wicker Park is kind of artsy and hip. The neighborhood is a little rough despite the strong pressure of gentrification.

Closer to the hotel is Logan Square, which is a neighborhood with a large hispanic population. You can get off at the Logan Square station.

There are several interesting north-side neighborhoods in Chicago. To get to these with mass transit you'll have to take a bus (or a taxi of course). Fullerton and Clark may be a good starting point. All of Clark Avenue is interesting (as is its neighboring street Broadway). At Addison and Clark you are in Wrigleyville, home to many sports bars and some improv theater. This area is generally fun to wander around in, day or night.