Chicago: Relaxing in a Windy City Wonderland

Chicago can be a beautiful place to visit for the holidays as long as you bundle up. There’s always a chance you might get stuck if the polar vortex hits us and shuts O’Hare down. But even if you have to spend a few extra days, there’s so much to do, you won’t mind. Promise.

Where to Stay

For a central city location and classic luxury, The Peninsula Chicago is your best bet, in the heart of the city’s best shopping, restaurants, and nightlife. Splurge for an executive suite (impeccably outfitted for both business and leisure travelers), and ask for room 1623, the only room with a bathroom overlooking Michigan Avenue. The spacious marble bathroom, with Oscar de la Renta toiletries, has everything your heart might desire, including his and hers sinks. For turndown service, plush holiday slippers are placed bedside and the flatscreen TV is elegantly turned out so I can relax in bed, watch the Travel Channel, and still enjoy the city panorama during commercials.

In the afternoon, enjoy a leisurely tea in the lobby and on Friday and Saturday nights, warm up with the chocolate bar. The tantalizing chocolate buffet is like a refined version of Willy Wonka’s factory, including a hot chocolate sommelier custom-blending your drink to order.

Most hotels in the city are concentrated in the River North, the Gold Coast, and Loop. But head just a little west, and you’ll find the newest and most effortlessly hip accommodations in town at Soho House. There are only 40 rooms in this boutique property, with preference given to club members.

Where to Spa

Whether you’re staying at Soho House or not, the Cowshed Spa is a must-visit. Whether you’re feeling like a knackered cow, grumpy cow, or wild cow, you can pick the perfect body oil to fit your mood. Nyree helped me select a relaxing eucalyptus and lavender oil for my deep tissue massage, where she expertly worked through the tension in my shoulders. Afterwards, I tried the signature Cowshed facial – the most popular facial for good reason. I almost fell asleep while Mercedes gave me a long and luxurious facial massage with raspberry seed oil (there’s also cranberry and evening primrose depending on your skin type) followed by a revitalizing palmarosa mask.

The Peninsula Spa, a serene oasis on the top two floors of the hotel, offers a totally different experience. Asian and Ayurvedic treatments are specialties – you won’t find a jade hot stone massage with a tea ceremony or a dosha specific wrap elsewhere in town. My dosha was vata on my last visit, so a relaxing clove and cinnamon oil salt scrub and mustard seed masque helped warm me inside and out. My massage therapist Melissa did an incredible job working out tension in my lower back. The serene and clean nail salon is worth stopping into for a mani or pedi as well. Ask for Aleks, who has been with the salon since the hotel’s opening 13 years ago, for gentle exfoliation and her impeccable eye for detail.

Where to Dine

The West Loop is the hottest food neighborhood in the city, with several delicious new restaurants as well as tried-and-true classics. If money is no object, shell out for the flora or fauna tasting menu at Grace, America’s newest three-star Michelin restaurant. For a more convivial atmosphere, Tête Charcuterie and Salero are my new favorites. Salero features Spanish-influenced cuisine although it’s far more creative than your typical tapas bar. Don’t miss the glazed pork belly with romesco and Calabrian chili. At Tête, although the housemade sausages and charcuterie shine, you’ll also want to try the vegetable cocotte.

What to See

You can check most of the names off your holiday shopping list after a half-day on the Magnificent Mile, and a detour on Oak Street for those with discerning taste. For a funny twist on a familiar Christmas classic, get tickets to Twist Your Dickens, an improvisational adult-comedy parody of A Christmas Carol. Second City actors take the Goodman Theatre by storm and will have you laughing ‘til your stomach hurts.

Where to Sweat

In the summer, I love rollerblading, biking, or jogging along the scenic 18-mile lakefront trail, but in frigid winter weather you’re better off inside. With three central Chicago locations, Equinox is a great bet too. Try the new Inside Out barre workout that combines core work, Pilates, yoga, and ballet to create long, lean muscles. If you’re staying at Soho House, their gym is pretty swanky too – complete with boxing ring and pommel horse.

Packing Tip

Bring a thick winter coat, scarf to protect your face and sturdy boots in case you need to trek through sludgy snow!