Ooh, I love the Segway tour plan! So many things I've yet to do. Like experience the glass-floor observation Ledge at the Willis Tower (still the "Sears Tower" to most of us, or, as I like to call it, my personal Tower of Terror). I really want to go, but it's so scary! If you plan to go, think about getting a
CityPass to save $$ and skip lines at many attractions, including Shedd Aquarium & Field Museum of Natural History, already on your wish list.
A fun freebie that should be on your must-do list: The Bean. Its official name is Cloud Gate, but it looks like a giant silver kidney bean. Really pretty, and makes cool pics reflecting surrounding buildings, or looking up at the middle of the underbelly from underneath.
When you're not strolling at Taste, you can check out restaurants on OpenTable's diner-voted favorites lists. Or just pick any Lettuce Entertain You restaurant. They're all pretty fab.
Attention, Shocker: Avert your eyes here, as I might happen to go into more "shop talk."

Anita, as I'm sure you noted, our only VB outlet is at the Aurora outlet mall, probably the best outlets. But if you're staying downtown, it's a bit of a drive, and rush-hour traffic could make for a looong return trip. Visiting outlets at either Huntley (tiny) or Gurnee (huge!) would let you return via a mall with a
Disney store.

Just saying ....
Hope your drive tomorrow is smooth & rain-free. Holler (or just PM me) if you need anything else. So excited for you to enjoy Chicago!
Oh, Jen, very excited for you and your prince, with the new job offer. Enjoy your new adventure!!!