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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.

A short drive from Amman, the town of Madaba is home to one of Jordan’s largest Christian communities and several impressive churches. Of these, the Greek Orthodox St. George’s Church is the most interesting. The church wasn’t built until the end of the 19th century, but during construction workers uncovered one of the most important surviving artistic relics of the Byzantine era: the Madaba Mosaic Map. Created by artisans in the 6th century, the mosaic was once an intricate map of Holy Land sites, covering modern-day Jordan, Israel, the Palestinian Territories, and Egypt’s Sinai. Only a quarter of the original work survives today, but even this fragment, which sits in the floor of the church, shows astounding detail. Look closely and you’ll see fish swimming in the Jordan River, the walls and gates of Jerusalem, Mount Sinai, and even the Nile Delta. There’s also an excellent exhibition next to the church to help you get the most out of your viewing.

What started as a hobby by Fred Koehler and his wife back in 1975, has turned into something that we all now reap the benefits of. Lynfred Winery was founded in 1979 in Illinois, of all places. Urged by some to take his talents to California, Fred refused to leave his roots and set up shop in Middle America. Over the years Lynfred has produced some award-winning vino, some of which you can sample in their tasting room in Wheeling. Grab a glass or a bottle and make yourself comfortable on the grassy lawn outside, or settle into a comfy chair in the tasting room/wine shop inside. Varietals range from Pinot Grigio to Viognier all the way to Syrah and Cabernet Sauvignon. Grapes are sourced from all over, with an abundance from California, and even a few from Washington and Chile as well. A visit to Lynfred Winery is the perfect way to while away a couple of hours over a nice glass (or two) of wine.

There are a handful of appealing options in the West Loop, but the most exciting is the Hoxton Chicago, whose laid-back lobby is filled daily with locals and guests working, meeting, dining, drinking, or hanging out with a coffee. Part of the socially focused Hoxton hotel group that launched in London’s East End in 2006, this 182-room hotel has become the West Loop’s top rendezvous spot for meetings (unless you’re a member of nearby Soho House), but upstairs is just as enticing. We love “Flexy Time,” which allows guests to check in and out whatever time of day they like, so long as they book directly through the hotel website.

Hello, rooftop pool! Leave it to Chicagoans to remain optimistic that summer will be amazing, even if winter lasts well into May. The rooftop pool (open to restaurant as well as hotel guests), occupies a prime spot on one corner of Six Points, that crazy intersection where three major shopping streets cross paths. That means the regulars are a mixed bag, but all come in for a good time, whether that means for brunch in the newly redesigned Café Robey street-level restaurant, to drink until dawn at the poolside Cabana Club bar, or to sneak up to its new sister, the Up Room, at the top of the deco tower.

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.

A recent makeover of the Four Seasons Hotel Chicago from Houston-based Rottet Studio did away with the dark and clubby vibe common in older Chicago hotels in favor of a brighter natural palette. Today, the lobby is open and bedecked in oversize floral arrangements; the open-plan lounge there, with its modern glass chandelier, has become a high-end local watering hole known as the Social Bar. The new Adorn restaurant is now a big-night-out dining destination courtesy of chef Richie Farina’s creations that range from a perfectly prepared filet mignon to caviar and eggs. Upstairs, the 345 guest rooms—more than half are suites—feature understated grays and pale greens and come with deep soaking tubs and (if you ask) unimpeded views of Lake Michigan.

Founded in 1971, the Wood Dale Historical Society is dedicated to the preservation of the history of this quaint Illinois town. One such monument to their efforts is the Adolph and Esther Rosenwinkel farm that was donated to the society back in 1982. The farmhouse itself was built in 1840, and the room pictured above is located in a second house on the property built by the same family in 1922. This structure features 10 rooms, and a full basement, which you can wander through during your free self-guided tour of the grounds. Start in the kitchen and work your way through the various rooms and nooks in this enchanting historical wonderland. All the rooms have themes ranging from the 1920s through the 1940s, complete with displays of fashion and interesting accessories of the times. The proprietors that I met were lovely, and took the time to show me around the entire place. So if you’re in the area, stop on in and meet Judi and Dennis, as they’d love to show you around the place. The Society doesn’t currently have a website, but please call 630-595-8777 for information, donations, and upcoming events.

Frenchmen Street is, more or less, the local-music version of Bourbon Street. It also has its share of tourists trundling about with go-cups in hand, but they’re drawn more by the music than the drink. Plan to spend an evening (things start to pick up around 8 p.m., earlier on weekends) along a three-block stretch of small, informal clubs where there’s often no cover (give generously and give often when the bucket comes around), or at most $5 or $10. Notable clubs include the Spotted Cat, the Maison, Blue Nile, D.B.A., the Apple Barrel, and Snug Harbor. Earlier in the evenings, there’s often an impromptu brass band at the corner of Chartres and Frenchmen. Between sets, take a moment to browse the night art markets, the largest of which is next to the Spotted Cat.

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).

This hotel is on our list of The 11 Best Hotels in Chicago.

Set directly across from the Art Institute of Chicago, this former members-only men’s gymnasium is now the Chicago Athletic Association, which is part of Hyatt’s Unbound Collection. Enter at street level off Michigan Avenue and walk toward the back to find a staircase that leads to the old swimming pool, now a venue for parties and pop-up concepts. Take the nearby elevator to the restaurant, Cindy’s, easily the best rooftop scene in the city, with highly Instagrammable terrace views overlooking Millennium Park, the swooping Frank Gehry–designed bandshell, and Anish Kapoor’s Cloud Gate (aka the Bean).

Park yourself in the second-floor lobby and hang with locals as they tap away on their laptops and sip lattes by the two oversize fireplaces. Walk through that expansive by Roman & Williams–designed room, where light beams in through ornate stained-glass windows, and you enter a warren of table games and darts, all festive and typically open to the public. There’s also the secret six-seat bar, the Milk Room, a relic of Prohibition, and the James Beard Award–winning Cherry Circle Room—a sexy, dark restaurant with a circulating martini cart and a meat-centric menu.

Upstairs in the 1893 landmark, 240 guest rooms reflect the building’s former life, with gym horses as foot beds, working fireplaces in some rooms, plasterwork ceilings, ornate carved wood wainscotting, and a clubby vibe. Some of the rooms are rather small, but the location is hard to beat, and the cozy, wintry ambiance makes it a popular (and fun) place to spend a weekend. And because the CAA keeps an eye on its water conservation, sources its food locally, and adheres to strict recycling standards, eco-conscious travelers can feel good sleeping here.

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.

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.

Two plane flights, plus a drive and you arrive to this tiny island off the coast of Mozambique in the Bazaruto Archipelago. The former Indigo Bay Hotel was the nicest accommodation on the island when it opened in 2001. In May 2014, the property was touched up and relaunched by Anantara, giving travelers a comfortable base to experience Bazaruto’s natural beauty and local culture. The hotel has its own in-house naturalist and a whip-smart, PADI-certified dive instructor who can take guests snorkeling and diving. The Bazaruto Archipelago has been a national park since 1971 and is home to more than 100 species of coral, four types of whales, sea turtles, mantarays, dolphins, and it boasts the largest population of the rare dugong on the African east coast. In addition to water activities, Anantara can arrange cooking classes, horse riding, dune boarding, and bird watching (Bazaruto is home to 180 species of birds).

But this resort isn’t only for active types. It equally caters to sybarites who are seeking R&R in a remote place. The 44 villas are all spacious and many come with large outdoor patios with dining areas and plunge pools. A highlight is the spa, perched high above the property. Make sure to arrive early and save time after to truly enjoy the views. The resort works closely with the local community, many of whom are employed by the hotel. Guests can visit one of the local villages and observe some of the community projects Anantara helps fund. But the best way to get to know the locals is simply by interacting with the friendly staff.

Guests at Anantara Bazaruto Resort can opt to explore this very different side of the island by sandboard (think snowboarding down sand dunes), safari Jeep, or on horseback. I went on a horseback ride up at sunset. The uphill was lovely, but going down a towering sand dune atop a horse is about as scary as dropping down a double black diamond run on skis. But my horse mastered the vertical drop expertly. More terrifying than the drop was the ride around the freshwater lake, which my guide said is inhabited by 12-foot long Nile crocodiles. Luckily the few we saw were snoozing far away.

The real voyage of discovery consists not in seeking new landscapes, but in having new eyes. ~ Marcel Proust. For my inaugural highlight on AFAR, I am starting with my wife’s favorite quote, and a local sight in Chicago. Sometimes people feel they must jet off to some far off exotic place in order to ‘travel.’ However, if you gaze anew at your immediate surroundings with fresh eyes, you will discover an entire host of wonderful surprises. Here we have Cloud Gate, located down in Millennium Park, back before they buffed out the seams. The contrast between the organic form of ‘the bean’ and the structured grid lines, along with the warped fun house mirror quality of the city, makes this a truly unique destination.