7AM: Check into the Hotel Lincoln and start the morning with a walk, jog or bike ride along Lake Michigan. The Lakefront Trail stretches 29 kilometres along Chicago’s eastern side, offering gorgeous views of the lake, long green pastures, multiple harbours and beaches, and bucolic paths winding from north to south.
8AM: Indulge in a world-class breakfast at Floriole Café & Bakery, the cosy French-inspired space run by couple Sandra and Mathieu Holl, where the custardy quiches are made with thick, flaky crusts and the colorful pizzettas decorated with fresh ingredients such as squash blossoms and crème fraiche.
10AM: Head downtown to the Gold Coast’s Blake, an insider's haunt for European luxury brands, mainly designers and couture houses from Paris, Milan and London. The arid decor of a former post office turned multi-brand emporium is offset by the warmth of the welcome and cutting-edge style advice.
11AM: Take in some masterpieces at the Art Institute of Chicago, which holds world-class collections including works by Pablo Picasso, Henri Matisse and Rene Magritte. Crowds usually gather at Georges Seurat’s A Sunday on La Grande Jatte; less so at Marc Chagall’s America Windows.
12:30PM : Stroll through the Loop and cross the river for lunch at Publican Quality Meats, a modern butcher shop with a loyal lunch following. Enjoy handcrafted sausages and creative sandwiches in this Fulton Market shop, located in Chicago’s old meatpacking district.
2PM: While near the West Loop, browse limited-edition furniture from local designers at Morlen Sinoway Atelier. The interior design store also carries artisanal jewelry, ceramics and glassware in a tony space at Fulton Market.
3PM: Pick up some new books at Seminary Co-op. The independent, cooperative bookseller stocks new novels, architecture and design titles, as well as hard-to-find academic volumes, much to the delight of its more than 53,000 members.
4PM: Relax with a cup of tea at The Drake Hotel – specifically, the Palm Court, an elegant lounge with a harpist playing most days. While there, take in the rest of this magnificent hotel.
6PM: Give in to the pleasure of a massage at the Peninsula Spa. The mix of house essential oils is a delicately scented delight, the pressure of hands is in tune with your body, a dive in the pool, with free access for two hours, is heavenly.
8PM: Get your fill at Monteverde, the restaurant of chef Sarah Gruneberg, formerly at the legendary Spiaggia, which is no more. Her fresh, handmade pasta is available to take away, in case you can’t get a reservation. Otherwise, opt for the Cacio Whey Pepe with ricotta whey – the house’s signature dish.