Chicago in six stops

More than the sum of its deep-dish pizza, this midwestern city has culture in spades, discovers Blossom Green

1 Potter along the banks of Lake Michigan to Grant and Millennium Parks, where you’ll find Anish Kapoor’s iconic bean-like sculpture Cloud Gate amid autumnal gardens. The Art Institute of 2 Chicago and The Field Museum are nearby. Laugh your jet lag away and catch one the city’s legendary improv shows at The Second City, where the likes of Bill Murray have graced the stage. Then head to Chicago Blues for a nightcap; the venue captures the spirit of the 1920s music scene. secondcity.com chicagobluesbar.com

3 Staggering cityscapes come as standard here but two skyscrapers offer distinct viewing experiences. Book ahead to skip the queue at The Ledge in Willis Tower – the second tallest building in the US. Or try the John Hancock Building for an observation deck that tilts 30degrees above Michigan4 Ave. theskydeck.com 360chicago.com Open House Chicago (14-15 October) gives you access to some diverse hidden gems across 200 cool locations. Expect to delve behind the doors of mansions, churches, private clubs, unique office spaces and theatres all over Chicago. It’s a superb way to get a sense of the city, and better still, it’s free. openhousechicago.org

5 Think Chicago, think deep-dish pizza, right? Sure, grab a slice (try Pequod’s in Lincoln Park), but don’t limit yourself. The West Loop area heaves with on-trend restaurants like Girl & the Goat, Grace and Oriole, deli-style West Loop Salumi 6and CH Distillery, a pioneer in local vokdas and gins. Bed down at Ace Chicago, the newest hotel in town. It’s housed in an industrial concrete and glass warehouse and bedrooms are up-to-date and comfortable. Alternatively, Soho House offers the familiar warmth you get from staying at your stylish friend’s city apartment. acehotel.com sohohouse.com