Chicago is a city of many different faces. It’s sweltering in the summer and ice-bound in the winter. For every soaring skyscraper there’s a Prairie-style property with a porch. Fine-dining establishments brush shoulders with classic American diners. It may be hundreds of miles from the ocean but Lake Michigan creates the illusion of sweeping seaside views. We’ve ridden the rattling L train around the Windy City in search of our favourite hotels, from luxury lodgings in the Loop to a family-run find in a former publishing house across the river.