HandyMan and I will be escaping to Chicago for a few days and I can't wait. I've been to the city a few times and while past memories include lots of shopping and getting kicked out of bars (oh, the silly things you do in your 20's!), this trip will be filled with architecture tours, good eats, and shopping (because you can never have enough for that).

There will be lots of walking so I'm planning a wardrobe built for comfort and style. The weather will be typically spring-like: cool and warm with a chance of rain. Here's some of what I'm packing:

I love planning a travel wardrobe... you're forced to edit and come up with creative outfits and be prepared for any sort of weather.  I remember when we went to Paris and I felt like a complete schlump so now I like to dress in an understated but pulled together way when I'm travelling. Plus, dressing simply means more room in the luggage for purchases (are you sensing a theme here?)

Have you been to Chicago? I'm looking for good restaurant recommendations if you have any!