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6 International Direct Flights From Chicago, Starting at $210 Round-Trip

Chicago Airports + Flying
by Sarah Hartness Mar 17, 2023

One of the biggest benefits of being a Chicago-based traveler is having access to two international airports. Many Chicagoans don’t realize how many airlines and countries have direct flights out of either O’Hare or Midway International Airport.

The direct flights from Chicago below go to six international destinations – and because you don’t have to make any stops, you’ll arrive at your destination as fast as possible. It also means you don’t need to worry about getting stuck in a long customs line and potentially missing a connecting flight.

The two massive airports also have other amenities that frequent flyers will appreciate, including lounges, shopping, dozens of restaurants, and public transportation. If you fly a lot, you’ll definitely want to sign up for TSA Precheck or Clear to skip the long security lines – one of the downsides at large international airports like Chicago’s.

And some of the direct flights from Chicago below don’t have to cost you an arm and a leg, meaning you can travel around the world without breaking the bank. Want to fly to Asia, New Zealand, the Caribbean, or Europe? Below are some of the best and most popular direct flights from Chicago to international destinations. And not all of them cost buckets of money, as long as you can be a bit flexible with the dates you fly. In fact, they start under $300.

Direct Flights from O’Hare International Airport

O’Hare International Airport is one of the busiest airports in the world. People from all over the country make connecting flights here, but for Chicagoans, there are plenty of direct international flights.

Reykjavik, Iceland

puffin in iceland - direct flights from chicago

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Iceland is the closest European destination to Chicago, and the flight flies by compared to other transatlantic flights. Even if you prefer warm destinations, Iceland is a spectacular destination to visit.

Reykjavik is full of friendly people and interesting museums; for such a small country, there’s a lot of history. Reykjavik is also near the famous Blue Lagoon, a geothermal spa, and one of the country’s must-see destinations, even if it is a little crowded. Reykjavik is also a great place to stay if you want to take day trips to other parts of the country with or without a car.

When you leave the city, you can see volcanoes, waterfalls, black sand beaches, and glaciers. The country is small, so you can see many popular places (including famous national parks like Thingvellir and Snæfellsjökull in a relatively short time. You can rent cars just for the day or find any number of private and group day trips.

If you travel between September and April, you’ll have a great chance of seeing the northern lights. And since the country has 60 percent of the world’s arctic puffins, you can spot the cute black-and-white birds year-round. It’s a fantastic adventure for a mere six-hour flight.

Read more about Iceland:

Copenhagen, Demark

copenhagen denmark at night - one of the best direct flights from chicago

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Copenhagen is one of the most popular destinations in Scandinavia, probably because there’s so much to do near the city. Tivoli Gardens is a vintage amusement park where you can let out your inner child on rides like the death-defying Sky Tower. And make sure to spend time walking around Copenhagen (perhaps via a free walking tour) so you can see the colorful buildings and learn about Danish culture.

The city is beautiful and feels like being in a fairytale. But if you want to make all your prince or princess dreams come true, make sure to visit Rosenborg Castle and the Christiansborg Palace. Both are architecturally stunning and have a lot of interesting history.

The flights to Copenhagen are relatively cheap compared to many nonstop flights to Europe from the US, especially during the peak summer season. You can use one of the direct flights from Chicago to Iceland and Denmark for anywhere you want to go in Europe, even if Copenhagen or Reykjavik aren’t your final destinations.

Read more about Denmark:

Tokyo, Japan

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Tokyo was closed to tourism for years due to the COVID-19 pandemic but now seems more popular than ever. It’s a long flight to the city from Chicago, but not having to transfer flights makes the journey seem more doable – especially if you’re the kind of person who can sleep on planes.

Tokyo is one of the best cities in Japan for learning about both modern-day and ancient Japanese culture. From the temples and gardens to the museums and viewing decks atop skyscrapers, you can spend weeks in Tokyo and not experience close to everything the city has to offer. You could also fill a whole trip just seeing the city’s modern attractions, like multi-story gaming arcades and the “Golden Gai:” row after row of tiny, late-night bars that seat only six or eight people.

Tokyo’s restaurant scene is also amazing. Some serve traditional foods like soba, ramen, sushi, and gyoza, some are internationally inspired, and the bakeries have colorful and highly Instagrammable pastries and sweets. Shopping is also very key to Tokyo’s culture, and you’ll find hundreds of stores selling clothing, souvenirs, and toys, plus quirkier stores, especially in the trendy Harajuku District.

Thanks to the country’s bullet trains, you can also easily access the rest of Japan from Tokyo. Other popular destinations in Japan include Kyoto, Hiroshima, Osaka, and Mt. Fuji. You can reach all of them by train in a few hours or less (and cover your tickets with one JR Pass).

Read more about Tokyo:

Munich, Germany

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Munich is the capital of Germany’s region of Bavaria and is one of the most culturally interesting cities in the country. It’s also one of the easiest to reach, with a direct train that connects the airport with the city’s central Munich Central Station. Central Station is walkable to many of the best hotels in the city, as well as many of the city’s historical sites. That includes Marienplatz (this historic center of the city). as well as museums like the Palace Museum.

One of the prettiest places in Munich is the English Garden, one of the largest urban parks in the world. There, you can do everything from surfing to beer drinking, and it also hosts frequent festivals and events throughout the year.

And speaking of beer-drinking and festivals — Munich may be most famous for the annual Oktoberfest celebrations each September, but the city celebrates its beer culture all year long. In the summer, you’ll find dozens of outdoor beer gardens full of happy people socializing (and trying to city’s famous brews) sitting in the sunshine (often with live music). Visit in teh colder months, and you’ll get to experience the liveliness of the city’s many indoor beer halls, including Hofbrauhaus and Paulaner Bräuhaus, both of which celebrate the city’s Oktoberfest culture year-round.

Read more about Munich:

Direct Flights from Midway International Airport

Midway, Chicago’s smaller airport, also has some nonstop flight options, primarily to the Caribbean. But don’t rule it out just because it’s a little older: if you’re looking for warm weather, you’ll find great direct flights from Chicago.

Cancun, Mexico

direct flights from chicago - woman at chichen itza

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Cancun is one of the most popular spots for Americans for a warm, relaxing vacation. There are dozens of all-inclusive resorts in Cancun and the surrounding towns like Riviera Maya and Playa del Carmen. At these resorts, all your food and drinks are included in the price of your stay, so you just have to relax by the pool or beach and enjoy your vacation. It’s an ideal direct flight from Chicago if you just want an easy, relaxing vacation for a few days.

However, Cancun is also the entry point if you want to go to the increasingly popular Tulum. Tulum is well-known for its beautiful cenotes, great food, and energetic nightlife – not to mention jaw-droppingly beautiful hotels. You can head to Tulum to party on the beach or have a wellness experience and learn to meditate. There’s a lot of variety.

From Cancun or Tulum, you can also visit Chichen Itza, the Mayan ruins dating back to 400 CE. It’s one of the largest archeological sites in the world, and it’s easiest to book a tour that includes transportation and your guide. Some tours also visit cenotes where you can snorkel and swim. There are also plenty of smaller Mayan sites in Cancun and Tulum, including the ruins at Tulum Archaeological Park (which is also near some hip eco-hotels).

Read more about Cancun:

Montego Bay, Jamaica

man on raft in jamaica montego bay

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Another popular warm-weather destination you can reach on a direct flight from Chicago is Montego Bay. The nonstop flight is only a little longer than the one to Cancun, and Montego Bay also has plenty of all-inclusive resorts.

But if you want a relaxing vacation without an all-inclusive, you’ll find plenty of budget-friendly hotels and unique lodging options. Fortunately, it’s easy to reach gorgeous public beaches, including the beautiful Negril Beach. You can also book Airbnbs easily, some of which are walkable to top beaches.

Montego Bay has a lot of outdoor activities, such as horseback riding, zip lining, golfing, and biking. Or, head to a beach where you can find a lot of water sports, like kayaking, sailing, snorkeling, fishing, and scuba diving.

You can also find some great restaurants and bars in Montego Bay, where you can taste Jamaican food and get a taste of the island’s nightlife (and live music). You can also use it as a gateway for exploring other towns like Portland or Kingston. Be sure to find somewhere to listen to live music, as Jamaica has some of the catchiest music in the Caribbean.

Read more about Jamaica:

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