Whether you’re looking for a weekend getaway or a two-week trip to a foreign country, these dream destinations are a direct flight from Chicago. No lengthy layovers to tire you out, no chance of your bag getting lost halfway, and no worries about missing your connecting flight!
Mayakoba, Mexico 
Flying into Cancun’s crowded airport and seeing Señor Frog’s face staring at you, it’s hard to imagine that just 40 minutes away is a lush mangrove ecosystem home to the most luxurious resorts in Mexico.
In Mayakoba, three world-class resorts are nestled within carefully preserved mangroves. A fourth, Hyatt’s Andaz, opens in December. Rosewood  and Banyan Tree  (the Thai brand’s first North American property) are the most impressive, with very different styles but a similar attention to detail and level of service that surpass everything else in Riviera Maya. Upon checking in at both, you’re offered a chilled glass of sweet green juice — chaya, the Mayan drink of life. Suites at both resorts are spacious yet intimate with outdoor pools and elegant interiors. Rosewood has a lighter feel, constructed with limestone, while villas at Banyan Tree fuse Asian design with Mexican details.
Dedication to sustainability is apparent throughout — from Domenico Vacca toiletries in glass vials at Rosewood to complimentary bikes for guests. With so much to explore, including the charming El Pueblito  town square, it’s fun to cycle instead of waiting for a golf cart pickup, also complimentary around the clock. Work up an appetite for Punta Bonita ’s tacos and tlayuda during the day and Casa del Lago ’s Italian-Mexican fusion or Saffron ’s authentic Thai cuisine at Banyan Tree come evening.
Kayak through the lagoons and marvel at the flora and fauna thriving in the clear waters. While dad is playing a round of golf on the stunning El Cameleón  course (home to the only PGA tour event in Mexico and a Certified Audubon Cooperative Sanctuary), mom will enjoy relaxing at the spa.
Open your mind and heart to the Kuxtal Sensory Garden Ritual at Sense, a Rosewood Spa . Meditate and intuition will guide you to choose a plant for your customized massage. Afterward, refresh with a flute of hibiscus juice while listening to the waterfalls and birds. It’s rare that a massage transcends the physical to offer emotional, spiritual and mental nourishment. Banyan Tree Spa  is renowned for its skilled Thai-trained therapists, but the stingless Mexican honey bee steals the show in the Melipona Honey Bliss body treatment. Honey scrub and massage oil transform even the roughest skin, making it sensuously soft.
More than any other resort community, Mayakoba fosters an authentic connection to Mayan culture and stewardship for nature.
This hippy, liberal bastion in conservative North Carolina is full of artisanal food, breweries and quirky shops nestled in the Blue Ridge Mountains. Stay downtown at the five-room bed and breakfast Bunn House  for a true taste of Southern hospitality, with five-star modern amenities in a restored brick mansion.
Explore Asheville’s renowned arts district with glass artist John Almaguer  and Asheville Art Studio Tours . Intimate tours are personalized to your interests. You can eat tasty neighborhood fare with Michael Hofman  off his own handcrafted porcelain dishes  or try your hand at glassblowing in John’s own studio . Then treat your tired feet to some pampering at Wake Foot Sanctuary & Spa . A relaxing foot soak with house-blended herbs and essential oils paired with a foot and leg massage is pure heaven after a full day of touring and exploring.
Have dinner at Red Stag Grill  for great game meats or Smoky Park Supper Club  for wood-grilled everything. This shipping container restaurant under a highway pass is not one you’d normally stumble upon, but after your first handful of spicy sweet bacon crackerjack, you’ll be addicted. End the evening with a chocolate and ice cream dessert at French Broad Chocolate Lounge , where they import cacao beans to painstakingly make all the chocolate for a plethora of bonbons, gelato, pastries and cakes, taking bean-to-bar to a whole new level.
You could spend an entire day or two traipsing the 8,000-acre Biltmore Estate , the private Victorian-era residence of George and Edith Vanderbilt. Various house tours will appeal to history buffs and fans of “Downton Abbey” while kids have plenty of activities to choose from including horseback and carriage rides, a petting zoo at Antler Village and motoring around the grounds on a Segway.
Portland, Oregon 
This city is foodie heaven. From sandwiches at Lardo  to soft serve at newly opened Wiz Bang Bar  to a lively rooftop dinner party at Departure , it’s nearly impossible to have a bad bite. Luckily it’s easy to be active here too. Stay at Kimpton’s Hotel Vintage , where you can rent complimentary bikes and go for a ride to Mount Tabor Park . It’s an uphill battle to get there, so on the way back reward yourself with brunch at Coquine  and try their buttermilk buckwheat biscuits and hazelnut cocoa nib granola parfait. The Hairy Lobster  and Han Oak  are a couple of newer favorites worth trying as well.
If you have a few extra days, get out to wine country. The Willamette Valley is just 45 minutes from the city, a much easier drive than from San Francisco to Napa Valley. Pinot noirs and chardonnays from Bergstrom  and Adelsheim  are often compared to Burgundy, and there’s great sparkling wine from the likes of ROCO Winery , Soter Vineyards  and Argyle  as well. Stay at The Allison Inn & Spa , the only five-star resort around, and appreciate an impressive collection of Oregon art and lush landscaping, including a garden whose bounty you’ll surely savor during dinner at JORY Restaurant .
Nature is at your fingertips in this friendly city surrounded by the ocean, mountains and forests. Even the downtown area is relaxed and cheerful instead of hectic and businesslike. Maybe it’s because they have the mildest climate in Canada and some of the best seafood anywhere. Definitely spend some time enjoying Stanley Park (it’s even bigger than Central Park in New York!), whether by bike or on foot. Talasay Tours  leads a unique hike from a First Nations perspective.
For your seafood fix, dine at the Fairmont Pacific Rim’s Lobby Lounge RawBar  for sustainable and creative maki, nigiri and sashimi including a signature kabayaki house-cured sablefish. YEW Seafood + Bar  is another great option for quintessential Pacific Northwest fare. Start with the tacklebox in the lively dining room for a seasonal selection of the freshest marinated, steamed and raw seafood. It’s the Vancouver answer to charcuterie and cheese, although British Columbia makes great cheese too. You’ll find some at Granville Public Market , along with a distillery, brewery and silk, glass and ceramic artist studios. Visit on a weekday instead of a weekend, when the tourist hub becomes too crowded for comfort.
The art scene here is not to be missed. The Vancouver Art Gallery  and smaller Bill Reid Gallery  that focuses on First Nations artwork are within just a few blocks and the historic Gastown neighborhood  is home to several fantastic independent galleries as well. While in Gastown, swing by East Van Roasters  for bean-to-bar chocolate and coffee followed by L’Abattoir  in the evening for a cocktail (the avocado gimlet is to die for) and contemporary French food in an effortlessly chic yet rustic space.
When it’s time to rest, Four Seasons Vancouver  is the full package, with excellent food at YEW, a hidden gem of a massage spa suite and the most helpful staff. Alternatively, splurge for one of 10 brand new owner’s suites at the Fairmont Pacific Rim . The sleek, modern décor is a winning departure for the often old-fashioned Fairmont brand. Record players in each suite come with a stack of vinyl curated to your taste and there’s live music in the lobby lounge until 1 a.m. each weekend.
Shanghai, China 
This global financial capital is the most populous city in Asia and best visited during autumn to avoid the rainy spring and hot summer. Both Four Seasons Shanghai Pudong  and Four Seasons Hotel Shanghai  are excellent choices in a city teeming with luxury hotels. The Pudong property is smaller, with 187 rooms and sleek modern décor in the financial district. The Four Seasons in Puxi (west of the Huangpu River) was the first Four Seasons in China when it opened in 2002, located in the historic and cultural heart of the city, and the property just completed an extensive renovation in February.
The black granite floors and lacquered aged elm wood at Qin the Spa  are a stark contrast to the bright, warm tones in the guestrooms and lobby. You’ll feel like you’ve stepped back in time to ancient China until a technologically advanced ESPA facial brings you back to present day.
Shopping abounds, whether you’re looking for a custom-made qipao dress or any other bespoke garments at the fabric market. The gorgeous silk scarves at WOO  depict lush mountain landscapes and lotus blossoms. There’s a brand new Disney resort , just opened in June for the kids, and more serious culture mavens will enjoy the incredible array of Chinese sculptures, painted porcelain, jade and calligraphy at Shanghai Museum  in People’s Square.
For an exclusive peek into the former British Concession, take a walking tour of this Shikumen neighborhood with one of China’s most famous photographers, Wang Gangfeng. He grew up here during the Cultural Revolution and will show you a side of Shanghai that tourists don’t get to see. You can arrange a private tour through the Four Seasons Hotel Shanghai.
Dine at Shàng-Xí  for an elegant, intimate and authentic Chinese meal including the best steamed shrimp dumplings and supreme seafood soup I’ve ever had. Or cobble together dinner from the snacks on Wujiang Road. Vegetarians will savor the Chinese delicacies including countless rare and exotic mushrooms at Fu He Hui .
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