From ultrabudget to superplush service, an unprecedented influx of new international flights from Chicago—often priced at a steal, thanks to the beefed-up competition—makes it easier than ever to plot a far-flung, last-minute long-weekend getaway. We’ve got the skinny on 10 dream destinations—all no more than eight hours away and most accessible by direct flight from O’Hare. Why settle for another Netflix Saturday night when you can party in Panama?
Asian Street Food Excursion
Travel Time:4.5 hours
Nonstop Flights:Air Canada (daily), United (two to four daily)
When to Go:May to June, for North America’s best outdoor night market
What’s New:Air Canada added a direct flight last year for as low as $611.
What to Do:It’s all about the Chinese-centered Richmond Night Market. A street food extravaganza, this market, the largest of its kind on the continent, hawks everything from Cambodian chicken wings and ginormous barbecue squid to … socks. (They’re really cute socks, OK?) On day 2, go high: Hong Kong’s much-lauded Mott 32 opened an outpost this spring, bringing its haute Cantonese fare to the West for the first time. For dessert, tuck into the vegan Lavender Dream gelato at Umaluma in the city’s booming Chinatown.
Travel Time:6 hours
Nonstop Flights:Icelandair (five to six weekly), Wow (four to six weekly)
When to Go:February to March, to avoid the summer crush and to see the northern lights
What’s New:O’Hare’s first ultra-low-cost transatlantic carrier, Wow launched direct flights in July, which means you can jet to the land of fire and ice for $430 round-trip. (That’s in theory: A carry-on will set you back $29; a bottle of water, $3.) Not up for no-frills? Try Icelandair’s new-last-year flights from $540.
What to Do:Embrace the permafrost of the off-season. Snowmobile on the glacier Langjökull and hike through dreamy blue ice caves with Arctic Adventures (adventures.is). Relax at night in a steamy geothermal swimming pool under the hypnotic, otherworldly glow of the northern lights. If you’re there next February 1 to 4, check out the Reykjavík Winter Lights Festival, which features live music, theater, fashion shows, and more throughout the city.
Whiskey and Golf Getaway
Travel Time:7.5 hours
Nonstop Flights:Aer Lingus (two daily), American (seasonal daily), United (three to seven weekly)
When to Go:October to December, when fares drop and dry golf conditions peak
What’s New:American upgraded its seasonal direct route with the sleek, fuel-efficient Dreamliner 787-8 (from $578), which features improved humidity controls and robust in-flight entertainment.
What to Do:Just opened, the Pearse Lyons Distillery offers an alternative to the cliché of Guinness brewery tours. For $24, you get an inside look, three tastings, and, naturally, a church graveyard tour. Time your visit for November 25, and you’ll be able to go on a bender at Whiskey Live Dublin, which for $52 offers tastings in Dublin Castle from 40-plus distilleries. In between booze sessions, dry out on seaside courses like the 27-hole Portmarnock Golf Club (from $238 for 18 holes).
Culture Boost for the Kids
Flight Time:8 hours
Nonstop Flights:American (four daily), British Airways (two daily), Norwegian (four weekly), United (three daily)
When to Go:Spring, for the widest range of airline options
What’s New:Norwegian Air is launching low-cost flights in late March that’ll get you there and back for a mind-blowing $400. Or wait until May for an upscale ride on British Airways’ luxe double-decker Airbus A380 (from $680).
What to Do:Start at the Natural History Museum’s vast, staggeringly ornate Hintze Hall, which reopened in July with a full-scale blue whale skeleton suspended from the ceiling. Show the kids the original social network at the new Postal Museum, making sure to ride the old-school mail railway through London’s subterranean tunnels. Sneak in some art at the Tate Modern with a photography exhibit featuring works by Man Ray and László Moholy-Nagy that runs May 2 to September 16.
Fashion Field Trip
Travel Time:8 hours
Nonstop Flights:Air France (five weekly), American (daily), United (daily)
When to Go:September to mid-December, when fares can drop more than $1,000
What’s New:Air France expanded its service (from $750) into winter and late fall, while American (from $660) added to its fleet the Boeing 787-9, which includes bigger windows, better climate control, and a premium economy cabin (from $1,165).
What to Do:Get to the Musée Yves Saint Laurent Paris, opening October 3 inside Saint Laurent’s former atelier. On display: 50 designs, including a wedding dress (a nod to the tradition of ending fashion shows with a bridal look), and a wall of jewelry. Afterward, ditch your sneakers and fanny pack for hipper duds on a guided fashion tour with style coach Aloïs Guinut ($190 for two hours, dresslikeaparisian.com).
Travel Time:8 hours
Nonstop Flights:Iberia (daily)
When to Go:December to January, for the ultimate Christmas blowout
What’s New:Attention, modestly big spenders: Iberia added a premium economy class (from $1,389), easing transatlantic travel with wider seats that generously recline and two checked bags included.
What to Do:Nobody does the holiday season quite like Madrid, where elaborate Nativity scenes (think special effects and live animals), festive markets, and intricate light displays pepper the city. If you’re a real Christmas junkie, though, you’ll want to be there January 5 and 6 for the larger-than-life Three Kings festivities: Madrileños kick things off with a nighttime parade worthy of Macy’s and then open gifts in honor of the Magi and nosh on doughnut-like roscón de reyes cakes covered in glacé cherries.
Travel Time:5 hours
Nonstop Flights:United (weekly), Volaris (weekly)
When to Go:January to March, for prime beach weather
What’s New:In November, the ultrabudget airline Volaris launches direct flights seasonally on Sundays from $180 round-trip. United will bring back its seasonal direct Saturday flights in late December ($597).
What to Do:Overlooking Zihuatanejo Bay, the cliff-top resort La Casa Que Canta unveiled a new look in September with eight revamped suites. Top draw: lounging by saltwater pools with ocean views for miles, bucket of Corona on ice and ceviche at your side (from $410). If you absolutely must move around, stroll through the waterfront Paseo de Pescador in the early morning, when fishermen hawk the latest catch to local chefs. From there, hoof it to a full-on sensory overload at the Mercado Municipal, an exciting city-block-size labyrinth of stands selling fruit, whole skinned chickens, and Día de los Muertos skulls of every shape and size.
Luxe Nature for Two
Travel Time:7 hours (including layover)
One-Stop-Flights:American (three daily), Avianca (daily), Delta (one to four daily), Spirit (daily seasonally), United (one to six daily)
When to Go:January to March, the comfortable dry season
What’s New:Post-revolution, high-end boutique resorts abound—for half what you’d pay in better-known locales.
What to Do:The nine-casita Jicaro Island Ecolodge (from $620 for two) sits on its own isle, so arrive in Managua at night for a boat ride across the massive Lake Nicaragua under starry skies. The next day, kayak at sunrise or take a three-and-a-half-hour road trip to sandboard down the black volcano Cerro Negro, then return to the resort to eat dinner on a private floating dock. For a more adventurous stay, head to Nekupe Sporting Resort and Retreat ($1,300 for two), opened last year on a 1,300-acre private nature reserve in the tropical hillsides of Nandaime. There, you can go on a Nicaraguan-style safari (hello, ATVs and monkeys) in the shadow of the volcano Mombacho.
Impromptu Party Weekend
Travel Time:5.5 hours
Nonstop Flights:Copa (two daily)
When to Go:December to February, when it’s summer there and the bar scene peaks
What’s New:Copa begins doubling its daily flights in November.
What to Do:Roam the colonial-era neighborhood of Casco Viejo, Panama City’s answer to River North. Start with dinner at the, well, intimate Intimo (only 28 seats), known for its cocktail pairings. Then head to the semihidden Mula (it’s above a restaurant) for a few low-key pours before going full-scenester at the Strangers Club, opened in July by the team behind New York City’s popular bar Employees Only. (Try the Angie, a zippy, botanical gin cocktail infused with maracuyá.)
Travel Time:4 hours
Nonstop Flights:American (daily seasonally), Southwest (daily from Midway), United (daily seasonally)
When to Go:November to April
What’s New:Southwest upped its frequency this year, making it the only carrier offering year-round direct flights (from $547) to Montego Bay (90 minutes by car from Negril). But you’ll find cheaper fares from O’Hare on United (from $438) and American (from $506).
What to Do:If you are workout-obsessed, check in at the 166-room Hideaway at Royalton Negril (from $402), an adults-only resort opened in March that offers dozens of fitness classes weekly, ranging from boot camps to yoga, plus massages on the beach to recharge you in between. Want a more tranquil option? Try the Cliff Hotel, opened in 2015, where you can lounge in a saltwater pool embedded in the rocky shore or take classes in an open-air yoga pavilion, which will forever ruin your sweaty, windowless Bikram studio back home.