It may be known as Second City, but Chicago rivals any of the world’s great destinations from NYC to London to Hong Kong. Yes, Chi-town has everything: stunning architecture and museums, forward-thinking chefs, laugh-your-heart-out comedy clubs, a thriving craft brew scene, and so much more. With 77 neighbourhoods across the city, it’s impossible to see it all but we recommend you start with the show-stoppers in and around the Loop and Gold Coast (Cloud Gate, the Museum of Contemporary, an architecture tour along the Chicago River, to name a few). Then move beyond the city centre to explore smaller neighbourhoods like Old Town, home to the famous Second City comedy club, and Wicker Park, where you’ll find artsy boutiques and killer coffee shops.