Chicago is the birthplace of the skyscraper. Take a 90-minute guided tour with First Lady Cruises, run with the Chicago Architecture Foundation (architecture.org/experience-caf/tours/) , to see the city's skyline from the water. Whether its political or romantic, each skyscraper has a story that you would never know at street-level. If you are tight on time, take the 40-minute Shoreline's Classic Lake Tour from Navy Pier.
For a family-run experience, head to the Guesthouse Hotel (theguesthousehotel.com; from $169 per room) in artsy Andersonville. Thoughtful touches before you even check in include a welcome email full of Chicago tips. In-house afternoon tea is from the decadent local pastry shop Vanille. Downtown, Loews Chicago Hotel (Loewshotels.com/Chicago; room from $199 per room) offers city-slick service with a roof terrace and spacious rooms with great views. Both have free wifi.
Breakfast. Don't bother paying for it at your hotel. Venture out and explore. Wicker Park. Downtown, make your way to Yolk (eatyolk.com). Yes, it specialises in eggs but there are also sweet treats. Red Velvet French Toast ($11.50) hits the high notes. Wicker Park, aka hipsterville, is brimming with brunch options.
Another city, another cocktail. The door to the Violet Hour (theviolethour.com) is hidden beneath the ever-changing mural on the wooden building across from Big Star. Through the velvet curtains, sit back and sup a $13 pre-prohibition cocktail.
Head to south-side neighbourhood Pilsen for vintage shopping. Carlos from Knee Deep (kneedeepvintage.com) will don you out like the only Don one should be dressed like – Dapper. There's plenty for Hendricks fans too (Christina, not the gin). For all things US high street, stick to the Magnificent Mile. It is magnificent at what it does – mainstream. Don't miss Reckless Records. It's self-explanatory.
The Bean. It’s shiny, reflective and curvy but unless your holiday highlight is photo-bombing legions of selfie-takers, stroll past this funhouse mirror. Its real name is Cloud Gate by the way.