Chicago’s flag is a big deal. It flies in business districts and from front porches all over town. It’s seen on T-shirts and in tattoos. In it, four red stars stand for important things in the city’s history. The first star is for Fort Dearborn, the second represents the Great Chicago Fire, the third and fourth stand for the two world’s fairs that took place in Chicago. But, after a recent visit, we think this classy city deserves a fifth star for all its fabulousness (as do readers of Condé Nast Traveler, who recently ranked it the No. 1 Best Big City in the U.S. for a sixth straight year). Here are some top-rated things to do in the Windy City. —Noa Nichol
stay. One of the city’s newest hotels, The LaSalle Chicago, Autograph Collection, is not only perfectly situated in the heart of downtown but perched 21 stories above street level for a truly levelled-up stay. Gorgeously appointed with all the marble and mirrors, the property boasts oversized guest rooms and luxuriously appointed suites feature Beautyrest Black by Simmons beds, Calcatta marble-clad bathrooms with spacious walk-in showers, Lavazza coffee machines, mini-refrigerators, 65-inch UHD TVs, wood floors and Egyptian area rugs. Dining wise, Grill on 21 offers a modern interpretation on the classic American grill, with green smoothies and avocado toast for breakfast, a tartare bar for lunch (choose from steak or carrot options), and lobster bisque, caviar, filet mignon and more for dinner.
shop. A great way to shop Chicago—a city famous for its retail therapy—is to break things down into districts. For high-end and luxury, make for the famous Magnificent Mile or the historic Gold Coast neighbourhood. In Chi-town’s Andersonville area, find scores of independent retailers offering a variety of wares, from locally designed goods at Milk Handmade to music and media at Rattleback Records to fine Asian housewares at Five Elements Home. Our favourite secret shopping find, though, was along a single block of North State Street, where century-old storefronts, some with original doors (open gently!), house hidden gems like Café Crèmerie (don’t deny yourself a ripiene: flavoured gelato served in a natural fruit shell), P.O.S.H. (we could have spent hours perusing this an eclectic assortment of vintage hotel and estate Silver, restaurant dinnerware and European flea market finds) and L.A. Burdick Chocolates, famous for its chocolate mice.
see. After you’ve posed in front of Chicago’s famous silver Bean, seek out a few more under-the-radar landmarks and sites. Start in Millenium Park (dubbed the city’s “front yard”), where gardens and public art installations are awe-inspiring, before touring the Chicago Cultural Center across the street, which used to serve as the city’s central public library. Art abounds at the Museum of Contemporary Art, where colourful exhibits will keep your camera clicking. For a bird’s-eye view of the Second City, head to the Ledge at Skydeck Chicago: the highest observation deck in the United States, providing views of the city spanning up to four states and 50 miles on a clear day. Another great way to see the city at large? A Chicago by Night Cruise will introduce you to the city’s sparkling skyline after the sun goes down.
savour. From deep-dish pizza to the famously Ketchup-less Chicago hot dog, this city is known for plenty of fun foods. For bites that are a bit less, well, obvious, try the healthy fare (and signature “magic” cookie) at Beatrix, plant-based cuisine (like the jackfruit “crab” sandwich) at Althea and scratch-made salad and noodle bowls at True Food Kitchen. Then, take yourself out for treat; Chicago’s Museum of Ice Cream lets you learn all about everyone’s favourite frozen food in a multi-sensory manner, including a life-size pool of sprinkles you can dive into at the end!
soothe. Located in a restored factory from 1902, AIRE Chicago offers a journey through the traditional Roman, Greek and Ottoman ancient experience of baths. Massages and treatments are available, but just as pleasant—and healing, for both body and mind—is a simple self-guided circuit of the various pools, cold plunges and steam rooms that dot the space. For your spiritual care, book a 60-minute reiki and chakra healing session back at The LaSalle; performed in your hotel room by a holistic healer, this in-depth step-by-step method aims to transform trauma and limits into abundance, freedom and love. Energy blocks are identified and released through Reiki and the seven chakras (energy centres) are opened, leaving you refreshed and ready to make the most of the rest of your stay.