Guide to CHICAGO
Chicago cares about culture and they care about accessibility. So it makes sense that there are so many amazing museums and free events. In the Summer, take advantage of a free classical concert in Millennium Park, or in Winter, head over to the Christkindlmarket at Daley Plaza for some Gluhwein. There are plenty of other free (or cheap) things to do. My favorites include the Lincoln Park Zoo and the The Lincoln Park Conservatory. The Art Institute is a necessary stop for me but if great art isn't your thing, go say hi to Sue at The Field Museum. I also love getting on the "L" and seeing the city from a different perspective.
The first time I went to Chicago I was so tired from walking around that I fell asleep after dinner every night. Big mistake. Go out. Actually, don't even sleep at all. The Green Mill is open and playing jazz until 4 am. It's dark and cool, and Al Capone used to hang there. There's also Parlour Car, a great stand up comedy show every Thursday in the back room of Bar Deville. It's hysterical and this is coming from someone who doesn't really love stand up...or even like it.
Cindy's at the Chicago Athletic Hotel: The best views of Millennium Park. I love the Grey Garden cocktail. P.S. When taking the elevator back down stop at the second floor to check out the amazing lobby and game room.
Pump Room at Public Chicago Hotel: Glamorous drinking.
Three Dots and a Dash Descend the Catacomb-esque stairs to an incredible Tiki Bar.