Chicago?

[wrigley]

AXO Alum, it depends on what you want. There's something for everyone. On the Michigan Ave, check out Water Tower Place with it's multi-levels. The John Hancock is next door. You can have cocktails at the Signature Room and have a great view of the city. The Museum of Contemporary Art is nearby . Then there's State Street. Check out Marshall Field's and have lunch at the Walnut Room before it becomes Macy's in three months. You can be fancy and have afternoon tea with finger sandwiches at the Four Seasons or The Drake Hotel. Next to Millenium Park is The Art Institute. You can catch a show at the Chicago Theater or Roosevelt University's Auditorium Theater.

The Chicago Architectural Foundation gives great walking tours and riverboat tours of the city as well. I'd suggest making your reservations soon. They're usually booked in advance.There is a free trolley shuttle you can take to museum campus, which has the Adler Planetarium, the Shedd Aquarium, and the Field Museum. The Museum of Science and Industry is just a el stop away from downtown.

As for nightlife, you can catch live comedy at Second City where they have a wall of fame of those who've gone onto SNL. Then there's Improv Olympics in Lakeview. For live jazz there's the Hothouse on Balboa or The Green Mill in Uptown.

You can rent bikes at Navy Pier to go along the lakefront if you want to be active. Avoid The Excalibur. It's a tacky tourist trap.

Definitely check out Garrett's popcorn, the carmel/cheese popcorn combo is great. As for the best place for a hot dog, SuperDawg is a Chicago institution and that's on the northwest side of the city. Giordano's deep dish pizza is my favorite.