Chicago is known for architecture, museums, dining, and sports. Chicago is on Lake Michigan, and there are many boat trips available. The walking architecture tour is very good. Don't miss a trip to Wrigley Field, the second-oldest baseball park. Ask your concierge for restaurant tips. There are too many excellent restaurants to name them all.
Quick Tips:
Chicago affords you the ability to come on a budget up through first-class. It is the third-largest city in the U.S. Chicago's spring through fall are beautiful--winter can get very cold and snowy, but still very nice. It doesn't really warm up until May, so dress appropriately. Many Chicagoans spend weekends in Wisconsin and Michigan, so check out these locations for more rural getaways that can be combined with a trip to Chicago.
Best Way To Get Around:
Parking is expensive, so leave the car where it is and use taxis. Taxis are always available, and usually for less than you can get to restaurants, theater, museums, bars, etc.
The downtown area, Michigan Avenue, and river north area are very walkable. Remember, you are in a large city. Like any large city, it is best not to walk off the beaten path. Public transportation is excellent if you need to go a little further. Chicago's "El," the elevated train, will take you most places within the city. If you need to go to the suburbs, the Metra trains are comfortable passenger trains that operate on a regular set schedule.