Where I visited
A college friend's home base for both nights - explored Wheaton College and downtown Wheaton.
The city itself - the Bean, Wrigley Field, and the Riverwalk.
Day by day
Flew out at 4:10pm and landed in Chicago by 6. Got to a friend's place a little after 8:30, then wandered Wheaton College once it had cleared out for the night - a campus feels different when it's basically empty. Asleep by midnight, a short trip already off to a good start.
Drove into the city around 11 and grabbed lunch at Devil Dawgs before spending the afternoon on foot - the Riverwalk, the obligatory photo at the Bean, and a stop through the Chicago Cultural Center. Dinner was deep dish at Gino's East, which lived up to the hype, then back to Wheaton for a walk through downtown before calling it a night around 11:15.
Along the Chicago Riverwalk
The Chicago River
Took the train into the city in the morning and had lunch at Dove's Luncheonette. Spent the early afternoon making one last round through Chicago - Wrigley Field, one more look at the Bean, and a stop at F1 Arcade - before catching the train back to the airport by 3:30. Flew out at 7:40 and landed in New Haven around 10:30. Short trip, but a good one.
Wrigley Field
The Bean, Millennium Park
The Chicago Theatre
Map
Wheaton, a Chicago suburb, and downtown Chicago itself.