Downtown Chicago Riverwalk is an all-day adventure and tours for any personality type are available. Foodies can join the Chicago Riverwalk Food Tour where you get a sampling of the Windy City's most interesting refreshment spots. Millenials can participate in the Segway Tour where you can glide through the city on those two-wheeled contraptions. Or, just do it the old-fashioned way and meander along the river with your honey.
Stop by the winery for some drinks along the river walk.