A romantic date idea for Ashley and Alex in downtown Chicago could be: A sunset boat tour of Lake Michigan while enjoying a multi-course dinner prepared by a private chef on board. After the boat tour, take a stroll through Millennium Park and admire the skyline while indulging in some of the best cuisine that Chicago has to offer. End the night with a private rooftop dinner, where Ashley can enjoy stunning views of the city while indulging in gourmet dishes and sipping on wine.