Travel the city’s original highway: the river. There are a handful of tours that start from either Michigan Avenue or Navy Pier and usually last about an hour and a half, cruising up the river and out into the lake.
Chicago is an American architecture destination, and this is the best way to check it out. Time it right and your tour could end up with a skyline view from the lake just as the setting sun hits the buildings.
I think the city should consider hiring the guy who produced this vid. It’s a hell of a lot cooler than the photo mashup used to advertise the tour on chicagoline.com.