6 International Direct Flights From Chicago, Starting Under $300

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

Photo: Simon Dannhauer/Shutterstock

• Flight time: 6 hours, 5 minutes
• Airlines: Icelandair
• Lowest round-trip price in 2023: $599 (May)
• Where to stay: The best boutique hotels in Reykjavik

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:

• 7 spectacular day hikes from Reykjavík
• 8 museums in Reykjavík for huge whales, northern lights, and lots of penises
• Watch the northern lights from this Airbnb’s geothermal hot tub in Iceland
• Scuba dive between tectonic plates at the world’s most unique dive site

Copenhagen, Demark

Photo: ESB Professional/Shutterstock

• Flight time: 8 hours, 20 minutes
• Airlines: Scandinavian Airlines
• Lowest round-trip price in 2023: $572 (October)
• Where to stay: The best hotels in Europe for getting cozy this winter

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:

• 10 architectural wonders you must visit the next time you’re in Denmark
• 7 things that make Christmas in Denmark unique
• This spiral walkway in a Danish forest lets you walk above the trees
• Denmark’s new spiraling tower overlooks a stunning national park

Tokyo, Japan

Photo: URAIWONS/Shutterstock

• Flight time: 12 hours, 45 minutes
• Airlines: ANA, JAL
• Lowest round-trip price in 2023: $1,194 (Autumn and winter)
• Where to stay: 12 Tokyo Airbnbs in the heart of the city

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:

• Tokyo Insider Guide: How to eat like a local
• 5 of the best under-the-radar neighborhoods in Tokyo
• This rowdy alleyway is the best place to drink beer in Tokyo
• Poisonous pufferfish are a delicacy in Japan. Here’s how and where to eat them without dying.

Auckland, New Zealand

Photo: krug_100/Shutterstock

• Flight time: 16 hours, 25 minutes
• Airlines: Air New Zealand
• Lowest round-trip price in 2023: $1,667 (Autumn and winter)
• Where to stay: The 6 best luxury resorts in New Zealand

The direct flight from Chicago to Auckland is one of the longest nonstop flights from the midwestern city (and one of the priciest). But if you’re trying to fly halfway around the world, you’ve got to expect that it’ll take a few hours – though you can’t get there any faster than by taking a direct flight. And since it’s a long flight, you’ll get a meal service and have plenty of time to sleep (and adjust to the time change, ideally).

There are a lot of different activities in Auckland, most of which revolve around adventure travel. One of the most well-known is bungee jumping at the Sky Tower, where you’ll jump from the tallest building in the country and fall for 11 seconds. Not an adrenaline lover? Auckland has plenty of museums, parks, and hiking trails, and you can easily take a day trip to Waiheke – Auckland’s “wine island.”

From Auckland, it’s easy to rent a car and explore the country. Auckland is on the northern part of the North Island of New Zealand, and you can easily spend a couple of weeks road-tripping around the country from the city. No matter what you choose to do, spending a few weeks there is worth it after the long (and pricey) flight.

Read more about New Zealand:

• 20 years later, here’s how “The Lord of the Rings” changed New Zealand
• New Zealand’s South Island is pure magic: 6 natural wonders you need to see
• How to see volcanic Whakaari/White Island in New Zealand

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

Photo: Bucha Natallia/Shutterstock

• Flight time: 3 hours, 30 minutes
• Airlines: Southwest
• Lowest round-trip price in 2023: $129 each way (April)
• Where to stay: How a Marriott Resort became Cancun’s best spot for mezcal

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:

• This Mexico resort town has an underwater museum with 500 statues
• 11 Cancún Airbnbs for an unforgettable beach vacation
• Cenote Xux-Hah in Mexico is a gateway to the underwater world
• The Rosewood Mayakoba is the perfect mix of luxury and wellness near Playa Del Carmen
• 9 gorgeous Airbnbs for your Tulum bachelorette party
• Pablo Escobar’s former mansion is now a luxury hotel in Tulum, Mexico
• 11 all-inclusive beach resorts in Mexico for under $300 a night

Montego Bay, Jamaica

Photo: Jam Travels/Shutterstock

• Flight time: 3 hours, 45 minutes
• Airlines: Southwest
• Lowest round-trip price in 2023: $191 each way (April)
• Where to stay: The 10 best Jamaica Airbnbs with pools, beach access, and luxe amenities 

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:

• How to plan a trip to Portland, Jamaica’s under-explored eastern parish
• The 5 best tropical Caribbean cocktails other than the Piña Colada
• The most breathtaking Airbnbs in Jamaica
• 10 unmissable waterfalls in Jamaica you won’t find in tourist guides
• 9 fun things to do in the Jamaica Blue Mountains