Grab a drink at the rooftop and head up to the cupola to check out where Sohail popped the question and Rachel said "Yes"!
Walk out the front door of The Drake and shop your way down Chicago's Magnificent Mile.
Stop by Wrigley field for pictures in front of the stadium. Once you're done, grab a drink at Sluggers while testing out your skills in the batting cages upstairs, or check out the country music at one of Rachel and Sohail's favorites, Old Crow.