Driving The American Dream

Starting in Chicago and finishing in Detroit, Trish Halpin takes the road less travelled on a fun-filled adventure across the US Midwest

- Trish Halpin

It’s a quiet Sunday morning and I’m kayaking leisurely up the Chicago River when the word ‘Trump’ looms large into view. The massive sign is plastered on to the front of a 98-storey glass skyscraper, one of the 120 or so that shape Chicago’s skyline. Given the size of its owner’s ego, the branding is hardly surprising, but it jars: this city’s stunning architecture – from art-deco masterpieces to postmodern wonders – otherwise blends so beautifully. Our guide Kayla sums up her view with a sigh and ironic eye roll, and on we paddle.

The Windy City is the starting point of a family road trip I’ve planned with my husband Neil and our 13-year old twins Esme and Kit. We’ll be driving through the US Midwest, taking in two of the five Great Lakes (Michigan and Erie) and four of the eight states they span (Illinois, Indiana, Ohio and Michigan). Known as the fly-over states, because, well, people generally fly over them on their way between the east and west coasts, they actually have the best of everything the US has to offer, from dynamic cities and historic towns steeped in Americana, to sports, outdoor adventures and glorious scenery.