Chicago
The Magnificent Mile (http://www.themagnificentmile.com): Your shopping paradise, the stretch of Scenic Michigan Avenue is lined with brand name shops ranging from Chanel to Apple.
The Taste of Chicago (If you come in July, this is one event you do not want to miss. You can literally taste the whole of chicago in one place along the lakefront. Combine the view with food, followed by a short boat ride that takes you onto Lake Michigan and i believe within the City’s waterways.) Taste of Chicago and More
Staying places: The city’s Downtown is full of Hotels such as Allerton, Allegro, Hilton (5 mins from lake), Sheraton, Marriott, Intercontinental. You name it, it’s all there. Chicago Downtown Hotels
Sightseeing: There are tour trolleys that take you around the city on a landmark ride. Chicago Trolley & Double Decker Co.
Walking: Millennium Park is the place to be, and then you can walk down Magnificent Mile and check out the Art Gallery as well. Millennium Park
Entertainment: Chicago is big on Broadway shows. Infact the movie Chicago was based in Chicago, staged in the threatre called Chicago. It is one of the most well-known threatres in the city, there are other places as well such as the Cadillac Threatre. Plays are usually running several nights a week. Broadway in Chicago Show and Theatre Tickets
Time required to see it all: Sky’s the limit. I would say 5 days maybe sufficient if you plan to devote one day to each activity.
Mode of transportation for out of towners: The best mode of transportation for out of town visitors may be Public Transportation. The Chicago Transit Authority has a superb network of Inter-city Bus service as well as rapid transit (train/subway). CTA bus passes are easily available from any Western Union location, and can range from $5 for a one day pass (unlimited ofcourse), $25 approx. Weekly Pass (unltd.), $80 a monthly travel pass. Trips can be planned by obtaining a time chart for arrival/departure of buses/trains which is estimated to every stop. http://www.transitchicago.com/travel_information/trip_planner.aspx
Parking if driving: Parking is found in two modes in the city of chicago. One of the way is to find a regular parking meter, but it is nearly impossible to find public parking in the vicinity of Downtown (the see all place of Chicago). Second option is to park in a Paid Parking Garage and the charges vary ($12-$25/hour).
Game and Such: If you should arrive in winter, Chicago Bears are often found entertaining the die-hard fans. If you come during summer, you will have the pleasure of watcing City’s twin baseball teams (Chicago Cubs or Chicago White Sox).
Chicago Cubs have fans on the northside of the city. Chicago White Sox have fans on the south side of the city. And the rivalry is just one part of overall fun.
PS: Devon Avenue is Chicago’s Mini India/Pakistan.
PS2: Do not forget to cruise down scenic Lake Shore Drive, and stop off at the beach located along the lakefront. The most known/used exit for beachfront is North Avenue exit from Lake Shore Drive.