Chicago

Tony cruises around the Windy City, has a damn-good hot dog, has a drink with painter and blogger Bruce Cameron Elliott, and dines with Top Chef champion Stephanie Izard.

The Hot List

Win a $100,000 Trip to the Caribbean.
Join the conversation on Social Media!
Leaf-peeping, road trips, fun getaways and more!
Follow Us Everywhere

Join the party! Don't miss Travel Channel in your favorite social media feeds.