Top, clockwise from top left: Madeira, Portugal; Ho Chi Minh City, Vietnam; Big Sky, Montana; Riviera Maya, Mexico; Cape Town, South Africa; St. Lucia; Helsinki, Finland; Quebec City, Canada Photos: (Madeira) Getty Images; (Ho Chi Minh City) Courtesy of Hotel Metropole Hanoi; (Big Sky) Jeff Engerbretson; (Riviera Maya) Courtesy of Viceroy Riviera Maya; (Cape Town) Getty Images; (St. Lucia) Getty Images; (Helsinki) Emilia Hoisko Photography for Visit Finland; (Quebec City) Getty Images


Quebec City, Canada

Old World charm meets New World tastes

Old Quebec City
Old Quebec City Photo: Getty Images

Best time to go:October, when hotel deals pop up and the city’s cultural engine kicks into high gear

Getting there:Increased competition has pushed average fares down by a whopping 50 percent since last year; American is offering a $460 nonstop through October.

The intel:The ramparts and cobblestone lanes of Quebec City’s historic center feel as if they’ve been transported from Europe, and yet the youthful and proudly Francophone capital city offers a distinctly North American — and, given the favorable exchange rate, decidedly affordable — urban experience. The sleek Hôtel 71 (from $170) is in the heart of downtown and offers the perfect jumping-off point for a wider exploration of the city’s charms. Start with a breakfast of cretons (a kind of paté) and maple syrup at La Buche, a traditional sugar shack, then pick up some locally made Île d’Orléans cassis at the Grand Marché de Québec, the city’s new farmers’ market. Starting October 10, the Musée National des Beaux-Arts du Québec will be exhibiting the wildly eclectic work of the Québécois duo known as Cozic. Also slated for October: the celebrated Quebec City International Jazz Festival. Make a jaunt outside the city limits for a meal at Arvi, a buzzed-about avant-garde restaurant where the chefs double as servers, then treat yourself to a thermal experience at the Strom Spa Nordique, where sessions start at $54.

Helsinki, Finland

A mood-boosting wilderness

Nuuksio National Park
Nuuksio National Park Photo: Getty Images

Best time to go:October and November, to catch fall colors and seasonally available direct flights

Getting there:Finland is the least expensive Nordic country to reach from Chicago. Nonstop flights on Finnair through December 1 start at $720.

The intel:Finns claim that their connection to nature makes them the happiest people in the world (according to the 2019 World Happiness Report). Why not see for yourself? At Nuuksio National Park, you can race across a snowy landscape on a husky-drawn sled, gently swat yourself with a fan of birch leaves while baking in a sauna (it’s a tradition, don’t question it), and swim in an icy woodland pond (which Finns say is the best way to start the morning). If you choose to stay in the city, book a room at the new Hotel St. George (from $222), which has its own 400-piece contemporary art collection. Then admire the undulating architecture of Oodi, the city’s central library, which features its own cinema, indoor trees, and balcony views of the Finnish Parliament.

Lisbon and Madeira, Portugal

Two European hot spots for the price of one

Lisbon and Madeira
From left: Lisbon; Madeira Photos: (Lisbon) Courtesy of Turismo de Lisboa; (Madeira) Getty Images

Best time to go:October through December, for flight deals

Getting there:Thanks to increased service, fares to Lisbon have dropped 19 percent since 2018. TAP Air Portugal’s new nonstop gets you there in under eight hours (starting at $775, a lot less than what you’d pay in summer). The savviest move: The airline’s stopover program lets you spend up to five days in Lisbon before continuing on to Madeira at no extra cost.

The intel:In budget-friendly Lisbon, spend a few days at the Pousada de Lisboa (from $235), which occupies a citrus-hued building on the waterfront that once housed Portugal’s Interior Ministry. Use the Airbnb-like Portuguese website Eat at a Local’s to book a meal or cocktails at a Lisbon resident’s home. Or go to the other extreme and splurge on a chef’s table dinner at the two-Michelin-starred Belcanto, celeb chef José Avillez’s signature restaurant. An hour-and-40-minute connecting flight gets you to the island of Madeira, where the weather is breezy and summery into early November. Hike through mountains, sip the island’s namesake wine, and stay at the new oceanfront Savoy Palace (from $225), which boasts a 33,000-square-foot spa, six swimming pools, and botanical gardens.

St. Lucia

Serenity for two in a tropical Eden

Marigot Bay Beach
Marigot Bay Beach Photo: St. Lucia Tourism Authority

Best time to go:December, for a killer Christmas present

Getting there:Launching December 21, American’s new weekly nonstop ($1,272) may already be driving down competitor fares: United’s has dropped to $992.

The intel:Once reserved for spendy honeymooners, this gorgeous, Creole-speaking Caribbean destination is becoming more approachable for the rest of us. The mountainous island is home to hotels in every price range, but couples will find a sweet spot — and serenity — by seeking out lodging away from the crowded tourist areas near Rodney Bay and Castries. The Marigot Bay Resort and Marina sits alongside a turquoise bay peppered with superyachts, and yet a luxe room for two, with breakfast included, goes for just $249; for $200 more, you and your better half get an all-inclusive package, featuring dining at local restaurants like Masala Bay, which specializes in Indian fusion. The soaring topography offers abundant opportunities for adventure, but couples staying at Marigot Bay can ease into things with free yoga and Pilates or a guided ridge climb through a tropical forest. Need a tonic after all that exertion? Book a mud bath at Sulphur Springs Park.

Ho Chi Minh City, Vietnam

A dip into ultraluxe Asia for nonluxe prices

Reverie Saigon
Reverie Saigon Photo: Matthew Shaw Photography

Best time to go:November and December, for ideal dry-season weather

Getting there:One-stop flights on China Eastern (from $740) are among the cheapest you’ll find to Southeast Asia. Heck, you can even justify a little extra for the super-posh Cathay Pacific flight (from $777).

The intel:The dollar goes far in Vietnam, but the bigger reason to visit now is the explosion of affordable luxury accommodations. In the former Saigon, fancy hotels rivaling those in other Asian countries come especially cheap, including the wildly opulent, 39-story Reverie Saigon (from $227, which is about $600 less than similar hotels in Hong Kong). Excellent street food is ubiquitous, but target the nearby Ben Thanh Market for pho, toasted banh mi, and local beer (found at “bia hoi” spots), usually for a buck or less each. Or use the money you saved on lodging to splurge on the hotel’s daylong culinary tour (from $850) with celebrity chef Luke Nguyen (MasterChef Vietnam); he’ll show you everything from hidden local kitchens to rooftop lounges. Ho Chi Minh City is also a hub for low-cost airlines, making the rest of the country incredibly accessible. A two-hour flight to Hanoi costs just $90 on Jetstar. Stay at the French colonial Sofitel Legend Metropole Hanoi Hotel (from $281), Southeast Asia’s storied grande dame and host of February’s Trump-Kim summit.

Cape Town, South Africa

Art and the outdoors in the Southern Hemisphere

Athletic Club & Social, Table Mountain, Constantia
Clockwise from top: Athletic Club & Social, Table Mountain, Constantia Photos: (Athletic Club & Social) Courtesy of Athletic Club & Social; (Constantia) Getty Images; (Table Mountain) Emily Johnson

Best time to go:Mid-December (when a drastically shorter flight is introduced) through February, to hit peak summer in South Africa

Getting there:Taking the first-ever U.S. direct flight to South Africa (launching December 15 on United, from $976) requires connecting in New York for the 16-hour leg to Cape Town, but you still knock four-plus hours off the previous travel time. Plus, the increased competition is likely to start driving down fares.

The intel:A favorable exchange rate means big savings on the ground. The best place to spend your money: the Central Business District, a thriving art hub. Stay at the five-room La Grenadine (from $170), an unusual Provençal-inspired guesthouse. Nearby, you’ll find abundant pleasures: guinea fowl yakitori on the African-Japanese menu at the sultry Fyn; live jazz, Negronis, and vintage sports photos at the restored Athletic Club & Social; and free monthly First Thursdays art walks, when you can browse the arresting sociopolitical exhibitions at galleries like Whatiftheworld. Beyond the city’s boundaries, take a guided hike up the flat-topped Table Mountain, peek at the penguin colony at Boulders Beach, and enjoy a wine tasting in leafy Constantia.

Riviera Maya, Mexico

A beachside adventure near ancient ruins

Viceroy Riviera Maya
Viceroy Riviera Maya Photo: Courtesy of Viceroy Riviera Maya

Best time to go:January and February, for a quick escape in the depths of winter

Getting there:Plentiful direct flights from both O’Hare and Midway, including reasonable fares from United ($277) and Southwest ($205), get you to Cancún, the gateway to this storied coast, in just under four hours.

The intel:Hire a driver (from $70) for the one-hour trip from Cancún and check in at the Thompson Playa del Carmen’s new mod 27-room Beach House (from $249). It’s located between the surf and Quinta Avenida, a pedestrian-only shopping and nightlife district where you’ll be able to pick up a lucha libre wrestling mask as a souvenir. During the day, grab a map of the local underground springs known as cenotes and go snorkeling, marveling at the karst rock formations. A guided tour with Living Dreams Mexico (from $208) will take you to Mayan ruins, including jungle-shrouded Coba, where you can clamber up a huge pyramid, and Tulum, a once-sprawling port city where you’ll be tempted to invent a drinking game spotting selfie-taking influencers. For an elegant evening, try La Marea, the beachfront restaurant at the Viceroy Riviera Maya (doubles from $524); its wine list features a huge selection of small-batch Mexican wines not found in the United States. Or you could just shoot tequila poolside at the Thompson. Win-win.

Big Sky, Montana

The ultimate winter workout

Lone Mountain Ranch
Lone Mountain Ranch Photo: Courtesy of Lone Mountain Ranch

Best time to go:December, to find the lower airfares of early ski season

Getting there:American launches daily nonstop service to the gateway city of Bozeman on December 18 (from $446), adding to increased daily service from United that’s driven fares from Chicago down 26 percent since last year.

The intel:An hour’s drive from the Bozeman airport, Big Sky Resort (two-day lift tickets from $99) includes 5,850 skiable acres beneath the summit of 11,166-foot Lone Peak. The season starts early — Thanksgiving weekend — and offers the most consistent snowfall in the northern Rockies, with a yearly average of 400-plus inches of powder. That translates to reliably epic ski conditions on an uncrowded mountain with a never-boring variety of terrain, more than half of which is geared toward advanced or expert skiers. (But there are plenty of bunny hills for dabblers, too.) Through December 5, score a room for $99 a night at the resort’s new slopeside Huntley Lodge, or opt for a mod, cowboy-style cabin six miles away at Lone Mountain Ranch (from $359 per couple, breakfast included). Snowshoe the ranch’s forested trails and take a horse-drawn sleigh ride to a candlelit dinner, where a cowboy strums songs.