We highly recommend the Chicago Architecture Tour! There are a few different tour companies including Wendella and Shoreline, as well as some boutique guides. You can't go wrong with any of these. Given time of year, we recommend a morning or sunset tour.
Bridget's favorite restaurant in the city! Amazing Mediterranean food and solid cocktails. (Requires reservations in advance)
Coffee shop by the hotels - rated best latte by my sister, Katie
Really cool cocktails bar a part of the Alinea Group
Great BBQ
Great place to visit, but a little off the beaten path. We would recommend driving or taking an uber to and from.