Here are some great options if you're staying in the River North area:
EATALY: 43 East Ohio Street - this place is all of the rage of Chicago these days
DOUGHNUT VAULT: 400 1/2 North Franklin Street - a cult favorite at Kelly's office
GLAZED and INFUSED: 30 E Hubbard Street - for when Doughnut Vault runs out
XOCO: 440 North Clark Street - can't go wrong with Rick Bayless
DEEP DISH PIZZA: Many options in the area - Pizzeria Uno and Due, Gino's East, Lou Malnatti's, Pizzano's, Giordano's
GARRETT POPCORN: 625 North Michigan Avenue - go for the Chicago mix
HANCOCK OBSERVATORY: 875 North Michigan Avenue - from the 95th floor you get the best view of the city and the lake
MAGNIFICENT MILE: Michigan Avenue - potpourri of historic buildings, shopping and posh hotels
MUSEUM of CONTEMPORARY ART: 220 East Chicago Avenue - great modern art museum within walking distance of the hotels
Checkout some of our favorite websites for local happenings:


And here are some local transportation options:
Metra (Suburb Train): metrarail.com
Chicago Transit Authority (The "L" Train and Buses): www.transitchicago.com