Architectural digest

From the imposing Willis Tower, one of the tallest buildings in North America – and for 25 years, when it was known as Sears Tower, it was the highest in the world – to the majestic neo-gothic Tribune Tower, Chicago’s buildings look like they’ve come straight out of a movie set and give New York’s concrete jungle a run for its money. The best way to take them in is with a boat cruise along the lakefront. It’s a bit touristy and very popular, so book in advance. You can also do it at night for more spectacular views.

Hard-core design buffs, however, must venture much further than the city’s centre to see some truly incredible architecture. The residential suburb of Oak Park, a 20-minute drive from downtown, is where architect Frank Lloyd Wright had his studio and built many of his houses nearby. The first house he ever designed – and where he lived with his wife and children – is now part of the Frank Lloyd Wright Trust, which offers daily tours of his home, studio and surrounding residences. The tours give insight into to this genius of modern architecture, a notoriously difficult man whose incredible taste and refinement are apt reflections of the city he called home for most of his life. Stay cool From big chains unveiling new hipster-friendly concepts to boutique properties opening in artsy neighbourhoods, hospitality brands are in love with millennials. Freehand Chicago is yet another hotel catering to twenty- and thirty-somethings, who see their accommodation as a spot in which to hang out rather than just a place to rest their heads after a long day of sightseeing. A lively and laid-back vibe, super-fast internet, lounges where guests can meet fellow travellers, and vintage decor are the trademarks of this new breed of 21st-century hotels.

Housed in a refurbished 1920s art deco building just two blocks from the Magnificent Mile and surrounded by galleries and restaurants, Freehand Chicago is also a big draw among the locals, who flock to Café Integral to enjoy