Immerse yourself in all that the Windy City has to offer with these top hotels to book in 2026 Sign up to Simon Calder’s free travel email for expert advice and money-saving discounts Get Simon Calder’s Travel email Get Simon Calder’s Travel email Email * SIGN UP I would like to be emailed about offers, events and updates from The Independent. Read our Privacy notice Although it is often called “the Second City ,” Chicago is arguably incomparable. The Illinois city constantly ranks as a