Drop your bags off at your hotel, the Wit, a contemporary Hilton hotel right off the Chicago River on State Street. Your options are pretty limitless right now since you're at the center of Magnificent Mile, the State Street shopping district and the downtown theater district.
However, you're going to start by hitting up Macy's on State, housed in the historic Marshall Field's department store. Check out the Tiffany dome in the atrium in the southwest corner, the hundred-year-old clocks on each corner of the building, and the Walnut Room.
Take a stroll up to Michigan Avenue, cross the Chicago River and you're entering the Magnificent Mile District. Shop and walk until you get to the Water Tower Place, a multiple floor shopping mall where you'll find Godiva, Akira, Victoria Secret, Sephora, Lacoste and even a Chicago Cubs Memorabilia center.
Have lunch or an early dinner in their high-end food court with plenty of options ranging from Japanese to Italian.
If you're feeling something fancier, leave the Water Tower Place and check out Mike Ditka's restaurant attached to the Tremont hotel just around the corner.
Enter your second half of the day by taking the Red line "L" train from the Chicago stop to the Berwyn stop, where you'll walk half a mile west to the Andersonville neighborhood.