Your party of 4 will blow into The Windy City for a whirlwind trip that includes tickets to a taping of "Oprah" and the hilarious Second City comedy troupe. After all this time, Oprah is still the queen of daytime talk shows, and Second City has been making people laugh since giving comedians such as Bill Murray, Tina Fey and Stephen Colbert their start.  You can choose to stay 2 nights at the downtown Hotel Monaco or Hotel Allegro.

4 tickets to 'Oprah' taping

4 tickets to Second City, reservations required

2 rooms for 2 nights at any Chicago Kimpton Hotel