Chicago has always thought big, and the $8.5-billion O’Hare 21 plan — the biggest terminal expansion ever — is yet one more giant leap forward to transform the Windy City into a 21st-century metropolis. That’s all the more astounding when remembering that less than 75 years ago, the flat prairie land sprouted little more than apple orchards. World War II changed the area, establishing an air base and aircraft manufacturing facility that became a commercial airport, named after medal of honor winner Edward H. “Butch” O’Hare, soon after.

In 2018, on the eve of O’Hare 21, the airport added yet one more laurel to its crown by extending its reach, with direct flights, to all six of the inhabited regions of the world — joining just four other cities in the world with the honor. Travelers to O’Hare can now literally have the whole world in their hands by taking off to these nine popular destinations.

vancouver, canada

Hugged by deep blue oceans and majestic mountains, Vancouver is a year-round stunner, loved as much for its easy access to British Columbia’s celebrated outdoor playgrounds as for its sophisticated urban frills, including world-class museums, music, and dining. In sprawling Stanley Park, a 1,000 acres of beaches, trails and gardens welcome Vancouverites to bike, walk, and run along its famous and scenic 17-mile Seawall. The Stanley Park Totem Poles, nine pillars of colorful First Nations artistry, are also picture worthy. 

With more restaurants per capita than New York, Las Vegas, or Toronto, Vancouver has turned dining out into a sport as popular as hockey. The city’s multicultural profile means there’s a palate pleaser around every corner, including the ever-raging ramen craze. The newly opened Horin Ramen + Sake on Robson Street’s “Ramen Row” is a good place to start slurping. Granville Island is filled with local art galleries, Waterfront Theatre, the False Creek Ferries, whose scenic tours depart every 15 minutes. When the sun shines, it’s outdoor patio time. From a spicy Caesar at Local Public Eatery across from Kitsilano Beach to bubbly from BC’s Okanagan Valley at the rooftop Reflections in the posh Hotel Georgia, there’s no more Vancouver way to raise a glass.
– Kimberley Lovato

Direct flights to Vancouver from Chicago O’Hare International Airport are available on American Airlines, United Airlines, and Air Canada and take four and a half hours one way.

When it comes to silver screen glamour, Hollywood gets all the stardust. But just over the hill from that famous sign, is where the real magic happens thanks to more animation and production facilities than any other city in the world. See the sets of favorite films and shows on public tours of Universal Studios and Warner Brothers, or go online for free tickets to the Ellen DeGeneres Show and Conan. The popular car remodeling reality hit West Coast Customs invites visitors to tour its Burbank showroom of the same name, too.  

Grab coffee or lunch in the walkable Magnolia Park neighborhood and shop for the ultimate Tinseltown souvenir at It’s A Wrap, which sells clothes and accessories used in recent productions. For a more edible memento, nearby Martino’s Bakery sells teacakes, Burbank’s square cupcake since 1926, and the ultimate local treat. If gaming is your jam, the recently built and super high-tech Blizzard Arena for live Esports events has seating for 500 fans. The space was once where Johnny Carson and Jay Leno hosted The Tonight Show, filmed in Burbank for 42 years. At night, the recently spruced and polished Castaway restaurant is the place to go for sophisticated drinks in its new Green Room cocktail lounge or dinner on the outdoor terrace with unparalleled views.
– Kimberley Lovato 

Direct flights to Los Angeles from O’Hare International Airport are available on United, American, Spirit and Alaska Airlines and take four and a half hours one way.

burbank, california

The state government may meet in Montpelier, but Burlington is Vermont’s capital in just about every other respect — art, music, business, education, cuisine — you name it. Most of it clusters around the postcard-perfect Church Street Marketplace, a pedestrian-only promenade of fashion boutiques, gift shops, bars, eateries, and cafes. Serving as backdrop is Lake Champlain, which becomes an outdoor playground in warm weather, with boating, swimming, sunbathing, concerts, and festivals. The Burlington Bike Path is the cherry on top, running north-south along the lake for 14 miles through stunning scenery. Come evening, locals line up along the boardwalk in Waterfront Park for some of New England’s best sunsets.

With nearly 20,000 college students, Burlington maintains a youthful blush that keeps the city buzzing with arts, culture, and entertainment, from the quirky Radio Bean, with its swinging Honky Tonk Tuesdays, to the Art Deco Flynn Center for the Performing Arts. It’s in the South End Arts District that the hippest scenes can be found, as the former industrial district fills with art studios, bakeries, vintage shops, restaurants, and breweries. Start at ArtsRiot, a renovated warehouse now housing a live music venue and restaurant before hiking a few blocks further to find three craft breweries and a cidery.
– Mike Dunphy

Direct Flights to Burlington from Chicago O’Hare International Airport are available on United Airlines and take just over two hours one way. 

burlington, vermont

The marble columns of the Temple of Hercules stand watch from Amman Citadel, a hilltop open-air museum showcasing the city’s ancient roots. It’s the perfect vantage point to take in the sand-colored cityscape of Jordan’s energetic capital, where history is leavened by the energy of a young, multi-cultural population. Descend to the buzzing streets and there’s more heritage on display. Channel Amman’s toga-wearing past in the Roman Theater, visit the magnificent Al-Husseini Mosque, and go from prehistoric statues to cutting-edge restoration work in The Jordan Museum. 

Simmering with creative vitality drawn from all over the Middle East, Amman’s art scene is among the best in the region. After you take in the fundamentals at the Jordan National Gallery of Fine Arts, check out some of the city’s modish art galleries — favorites include the contemporary Dar Al-Anda and Orfali, a thoughtful curation of Arab artwork. Many of the finest galleries are concentrated in the Jabal Al Lweibdeh neighborhood, where you can sip tea in cafes that attract a chic local crowd. Duck into Rumi for a glass infused with cardamom and roses, or combine your pleasures at Fann Wa Chai, a tea shop and gallery where brews are paired with edgy canvases. 
– Jen Rose Smith

Direct flights to Amman from Chicago O’Hare International Airport are available on Royal Jordanian Airlines and take 11 hours and 30 minutes
one way. 

amman, jordan

Forested peaks vie with glass towers in Colombia’s mountainous capital — a cosmopolitan hub wrapped around a gently faded downtown. Cobblestone streets meet colorful street art here, and the city’s allure charms history buffs, late-night partiers, and travelers chasing Colombian cool. Check out colonial-era architecture in the walkable La Candelaria neighborhood, covet the pre-Hispanic trove on gleaming display at the Museo del Oro (Gold Museum), or visit the Museo Botero (Botero Museum) to see the artist Fernando Botero’s famously zaftig subjects in vivid color. However, it’s not museums alone that have an exclusive on Bogotá bling: a gilded altar at the historic Iglesia San Francisco (San Francisco Church) is one of the city’s most precious treasures. 

And like the rest of Colombia — a country that’s produced some of the world’s greatest racers — Bogotá has a love affair with bicycling. To get a taste of their passion for two-wheeled transport, from high-end racing bikes to cruisy clunkers, visit the city during the weekly Ciclovía event, when cyclists replace cars on 75 miles of Bogotá roads. Whether you’re racing the locals on a speedy rental or pedaling downtown for a Sunday breakfast of arepas and Colombian coffee, joining the Ciclovía is a chance to see the city at its most carefree.
–Jen Rose Smith

Direct flights to Bogotá from Chicago O’Hare International Airport are available on Avianca and take six hours and 15 minutes one way.

bogotá, columbia

You’re never far from the ocean in Auckland, an isthmus city whose harbors nearly split the North Island in two. For many travelers, this is the urban gateway to New Zealand’s sublime nature, but there are ample rewards for those who linger. Let’s start with the views: You’ll find 360-degree stunners from the summit of One Tree Hill or the Sky Tower observation deck. For a dose of New Zealand’s Polynesian heritage, head to the Auckland War Memorial Museum to catch daily cultural performances that build into a chest-slapping, foot-stomping finale of the Maori haka. 

To find out why the “City of Sails” ranks among the world’s most livable cities, visit the stylish Ponsonby neighborhood, where shops are filled with homegrown fashion. Perk up for an afternoon of exploring over lunch at Orphan’s Kitchen, whose chef brings a reverence for Maori heritage to an ultra-seasonal menu. From there, you’re just around the corner from The Shelter, a laundromat-turned-boutique that stocks local labels like Maggie Marilyn. The next stop is the Ponsonby Road location of Harman Grubiša, a womenswear brand from two of New Zealand’s edgiest young designers. Finish the day with a generous pour of New Zealand wine at Annabel’s.
– Jen Rose Smith

Direct flights to Auckland from Chicago O’Hare International Airport are available on Air New Zealand and take 16 hours and 20 minutes one way.

auckland, new zealand

There’s a lot to be said for exploring Ethiopia’s capital Addis Ababa for a few days. Temperatures never get too high (although the summer is rainy), and it’s one of the best places in the country to partake in Ethiopia’s passion for coffee, as well as to sample its music culture and unique cuisine. Start the day at a buna — the local coffee stalls on just about every street in the city — though do also look for branches of the chain Tomoca, where you can buy coffee beans to take home. Shoppers wanting to go deeper into the local retail experience can head to the Merkato, Addis Ababa’s most frenetic market, with stalls housed in corrugated sheds.

Visit the city’s oldest and most famous resident, the three-million-year-old, female australopithecine “Lucy” at the National Museum of Ethiopia, before checking in with one of the city’s more recent phenomena: Ethio-Jazz. Places like Jams Addis and Jazzamba play into the small hours and are a must for music-lovers, while many of the city’s restaurants double up as cultural shows, such as Yod Abyssinia where the injera is as good as the entertainment.
–Vanessa Able

Direct flights to Addis Ababa from Chicago O’Hare International Airport are available on Ethiopian Airlines and take 13 hours and 45 minutes one way.

addis ababa, ethiopia

Divided by the Danube River, the Hungarian capital splits into Buda and Pest. In hilly Buda, the Castle District, with its royal palace, views from Fisherman’s Bastion, and winding Baroque streets are a top draw, as are the many historic Ottoman thermal baths. In flat Pest, the ornately Gothic Hungarian Parliament Building strikes a dramatic pose. However, it’s nearby St. Stephen’s Basilica that’s the city’s most photographed spot. Behind the Basilica, Andrássy Avenue, which continental Europe’s oldest metro runs below, stretches over to City Park, home to a cluster of museums and the Széchenyi Baths, the largest in Central Europe.

Budapest’s nightlife congregates around the “ruin bars” of the VII District. These crumbling watering-holes decked out with recycled furniture and fairy-lights are crowd pleasers, the most popular being Szimpla Kert. Neighboring districts complement with creative counter-cultural spaces like socially responsible Auróra, where activists and cool kids rub shoulders at comedy nights and Balkan parties. A few streets away, art collective Painters Palace opens its basement for live drawing or creative writing sessions. Beer lovers drink up at Élesztő, a converted glass factory with 21 taps of Hungarian craft beer. After an IPA or two, many take in an avant-garde production next door at Trafó, a theater in an old transformer building.
– Jennifer Walker

Direct flights to Budapest from Chicago O’Hare International Airport are available on LOT Polish Airlines and take nine hours one way.

budapest, hungary 

It doesn’t take a long stay in Taiwan’s capital to realize that Taipei goes far beyond the limits of its industrial and manufacturing reputation. A vigorous city with gourmet appetites and a burgeoning creative culture, Taipei might just be your new favorite Asian metropolis. Get your bearings with a visit to the epic National Palace Museum and a ride up to the observatory on the 89th floor of the towering, pagoda-like Taipei 101 to soak up the panoramic view. One of the most unique experiences can be found at Taiyuan Asian Puppet Theatre Museum, where puppetry troupes perform with English subtitles.

Taipei really shines in its markets: for a local street dinner by the river, head to Raohe Market; if fabric is your thing, then check out Yongle Market for embroidered silk, cotton, satin, gauze, and Japanese prints. Take a break at the historic Wistaria Tea House inside a 1920s Japanese-style wooden house or light a stick of incense at the Longshan Temple. Built in 1738, it’s one of the oldest public buildings in the city. For a glimpse of Taipei’s contemporary arts scene, visit one of the “creative parks” like Huashan 1914, which started its life as a winery and sake producer more than 100 years ago.
–Vanessa Able

Direct flights to Taipei from Chicago O’Hare International Airport are available on EVA Air and take 15 hours and 40 minutes one way.

taipei, taiwan