Sam's exploring everything Chicago has to offer. From the delicious art of molecular gastronomy, to the improvisational comedy of Second City -- can the Windy City teach this die-hard New Yorker a thing or two about cool?

The Hot List

Enter Daily to Win a Trip to the Golden Gate City!
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.