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  • 1411 E 53rd St, Chicago, IL 60615
    Hyde Park is happening. Catering to the University of Chicago crowd and its visiting dignitaries, the five-year-old Sophy takes inspiration from hometown literary and musical heroes, whose artworks ornament the walls in the popular and always convivial Mesler restaurant. Taking the title of the first boutique hotel on Chicago’s South Side when it opened in 2018, the property occupies a prime spot on 53rd Street—a vibrant commercial hub lined with shops and restaurants owned and frequented by a diverse population that range from academics to local politicians to the city’s cultural influencers. Former UofC professor Barack Obama’s home (and his under-construction presidential library) are nearby.
  • No matter your passion, Portland has you covered. The tax-free shopping wonderland is loaded with stores to tickle the fancy of shoppers both casual and obsessed. From Powell’s City of Books—easily one of the best bookstores in the United States—to Wildfang, where the coolest patriarchy smashers hang, and, yes, all the chain stores, Portland’s got the goods. Some of the city’s shopping hubs include downtown Portland, Pioneer Place, 23rd Avenue, and the Pearl District. Fuel up with some java at the coffee shop of your choice because there is serious shopping to be done.
  • 50 W Washington St, Chicago, IL 60602, USA
    The second most famous public sculpture in Chicago is 50ft high, made of steel and no one knows what it means. It’s doesn’t even have a proper name so it’s just known as “The Picasso.” Pablo Picasso gifted this untitled sculpture to the city of Chicago in 1967 and it caused a big ruckus because, well, it’s weird looking and no one knew what it was supposed to be. A woman? A chimera? A face? Hard telling. We do know that it was the first modern sculpture installed in the downtown area and it’s now the pride and joy of Chicagoans and photographed almost as much as the Bean. On sunny days you’ll see kids sliding down that sloping steel base and I love that the city still allows those jungle gym antics on such famous real estate.
  • 365 N Canal St, Chicago, IL 60606, USA
    If you happen to be interested in architecture, or even if you are not, the Harry Weese-designed River Cottages located from 357 to 365 North Canal Street in downtown Chicago are something you should see. A native of Illinois, Weese is best known for his modernistic style which also focused on historic preservation. The wonderful River Cottages, a mesmerizing display of glass and steel square and triangular shapes, rests beautifully along the edge of the Chicago river. The ideal vantage point for taking in this architectural masterpiece is being perched on a boat in the river. Find a friend with a boat (challenging), or hop on the any of the numerous architectural boat tours originating from Navy Pier (easy), and make your way to Harry’s cottage.
  • 11 E Walton St, Chicago, IL 60611, USA
    This hotel is on our list of The 11 Best Hotels in Chicago.

    Designers Lisa Simeone and Gina Deary of KTGY Simeone Deary Design Group oversaw the original design of the Parisian-inspired Waldorf-Astoria Chicago in 2009, and the pair was once again brought in to breathe new life into this 215-room Gold Coast gem. Rooms are now bright white, well-lit, and include pops of uplifting magenta. Before you hit any of them, however, there’s much to entice at street level. Enter from the circular driveway and marvel at the Swarovski chandelier, modeled after a vintage brooch, along with the herringbone wood floors and black-and-white pinstriped stone. Don’t miss the Peacock Lounge and its secret sister, Bernard’s Bar, an intimate craft cocktail and champagne boîte, which is virtually unknown even by city denizens (which means you can always find a seat). Its Scottish and equestrian themes are almost as anachronistic as the Mansard roof and circular driveway, which just adds charm to this newly beloved Chicago hotel.

    The guest rooms feature oversize headboards and abstract floral bedspreads, while bathrooms are a marvel of marble. For something more, splurge on either the new 1,800-square-foot Astoria Suite or the redesigned 2,400-square-foot Presidential Suite, both of which will have you feeling you’ve been transported to a Parisian pied-à-terre (the latter’s primary bedroom features a fireplace).
  • 100 Linden Ave, Wilmette, IL 60091, USA
    Suburban Chicago isn’t the first place that comes to mind when you think of major religious centers. But Wilmette, a small town located less than 10 miles north of the Windy City, is home to the only Bahá’í House of Worship in North America. Dedicated in 1953, the temple—one of seven in the world—took more than three decades to build and features symbols from different world religions in its intricate design, signifying that everyone is welcome. An ornate dome crowns the nine-sided structure and symbolizes the unity of all people and religions under God. Visitors are welcome to explore the temple and surrounding geometric gardens. You can also call ahead to arrange a group tour.
  • 108 E Superior St, Chicago, IL 60611
    This hotel is on our list of The 11 Best Hotels in Chicago.

    Often rated the best hotel in Chicago since it first opened in 2001, the Peninsula Chicago keeps its reputation by offering the finest high-end Chinese cuisine in the city and easily one of the top hotel spas in the Midwest. The Magnificent Mile mainstay has 339 spacious guest rooms and suites, outfitted in an understated style with floral motifs by artist David Qian. Thoughtful details include soaking tubs with hands-free televisions, a table for two set beside a window with a view, and linens custom created by Pratesi.

    No stay would be complete without a meal at the Shanghai Terrace, where chef de cuisine Elmo Han earns accolades for his modern interpretations of Shanghainese, Cantonese, and Sichuanese classics. During the warmer months, you can dine (or just have a mocktail) on the actual terrace, the whole of Chicago displayed before you. Also required: an afternoon at the 15,000-square-foot Peninsula Spa, with its floor-to-ceiling windows, facials using Biologique Recherche products, and an Olympic-size pool and sun deck.

    Twenty-four hours before check-in, be sure to request “Peninsula Time,” which allows guests to access their rooms as early as 6 a.m. and stay as late as 10 p.m.—a lifesaver for international or early-bird travelers. And eco-conscious travelers take note: The Pen recently received Gold Status from EarthCheck, its second consecutive Gold Status award.
  • Inside the city’s most innovative restaurants, maverick chefs are defining modern Czech cuisine.
  • 330 N Wabash Ave, Chicago, IL 60611, USA
    This hotel is on our list of The 11 Best Hotels in Chicago.

    Chicago invented the skyscraper, and some of the world’s most elegant examples define the city’s skyline. You can stay in the coolest one of them all, designed by German American architect Mies van der Rohe and run by Langham Hotels. To access the Langham Chicago’s minimalist-yet-opulent 268 guest rooms (including 48 suites), you must first check in at the second-floor lobby; its ceiling is hung with silver pebbles, its sofas populated by stylish guests, and its David Rockwell–designed Travelle restaurant alive with music and bites by executive chef Damion Henry during coveted afternoon teas.

    The former IBM building with a black exoskeleton also houses a Chuan Spa, which specializes in such Eastern therapies as acupuncture, cupping, and gua sha. A 67-foot-long indoor pool and full-service fitness center are available to all guests.

    Anyone spending the night in the rooms, with floor-to-ceiling glass windows framing Chicago views, has access to one of the city’s best concierges, who can organize a River North food tour, a Frank Lloyd Wright walking excursion, or a mixology class at Travelle. Don’t leave without taking a photo beside Jaume Plensa’s “Anna” sculpture in the Wacker Street lobby—then walk over to Millennium Park to see his larger works on display.
  • On a trip with a young traveler in tow, a writer reflects on her first Venice adventure—and how it changed her life.
  • Tourism is down, prices are up, social services are disappearing, and the government is bankrupt. Which means it’s a good time to get to know Seychelles.
  • 249 East Irving Park Road
    You’ve probably had the sauce, but did you know that there are three different places in Illinois where you can actually go and eat at a Sweet Baby Ray’s restaurant? With locations in Wood Dale, Elk Grove Village and Chicago, there’s no excuse. Falling under the label of ‘authentic urban Chicago style barbecue,’ Ray’s creative menu has a distinctive southern twang to it that everyone loves. Known for their ribs, chicken, pork, and awesome sandwiches, Ray’s also has a host of other craft choices. Spruce up your meal with one of the seven homemade sides, try the gumbo, or get your greens by adding a freshly made salad. And if you feel the need to take something home with you, there is a full selection of barbecue sauces that you can purchase for your very own culinary adventures back at the house.
  • For cross-country skiers, one winter destination rises above the rest: humble Hayward, Wisconsin, where, for a glorious weekend, their obscure sport is king.
  • Hail to New Mexican food—a melting pot of Spanish, Mediterranean, Mexican, Pueblo Native American, and cowboy chuckwagon. The best New Mexican cuisine is earthy and home-style and includes dishes such as tamales, chiles relleños, green chili cheeseburgers, and enchiladas. The official New Mexican state question is “Red or green?” Your answer depends on the kind of chili sauce you want smothered on your dish. Unsurprisingly, the state hosts some of the best New Mexican food you’ll find anywhere.
  • After a string of personal losses, a writer heads to Tamil Nadu seeking solace from her sorrows. It takes two temples, a palm leaf astrologer, and the driver of a velour-lined taxi to make her feel whole again.