How to find the cheapest flights from the US

Travel hacks

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August 12, 2021

By | August 12, 2021

Where are the cheapest places to fly from the US and how can you find the best deals? Kiwi.com of course!

Have you tried searching for trips with Kiwi.com? It’s easy! Our Kiwi-Code checks over two billion prices every day, so you’ll always be sure you’re getting the best price. Try searching To: Anywhere and you might find yourself a vacation you’d never even thought of for just a couple of bucks! Here’s just a tiny selection of the great deals Kiwi.com has from cities across the US.

San Juan, Puerto Rico from Philadelphia

Old, colorful street in San Juan, Puerto RicoOld, colorful street with Spanish colonial-style houses in San Juan, Puerto Rico — Shutterstock

Home to around a third of the population of Puerto Rico, San Juan feels more like Miami than comparable Caribbean capitals like Kingston. And, even though the influence of the US is keenly felt (it’s home to the Caribbean’s largest shopping mall, for example), another major draw is its historical mix of cultures that blend beautifully.

Old San Juan is a combination of Spanish colonial style, laid-back island life, and a twist of US modernity. It’s here you’ll find the best bars, shopping, and nightlife, as well as scores of places to stay. Either spend your time exploring, or head out to the beaches for a spot of well-earned relaxation.

Aruba from Atlanta

White sandy beaches with Flamingos on Aruba islandWhite sandy beaches with Flamingos on Aruba island — Shutterstock

A part of the Netherlands flung far away in the Caribbean, Aruba is an alluring destination: miles of white, sandy beaches, all-inclusive resorts meaning you never have to want for a thing, and a range of things to do from water sports to hiking, horse riding, and cycling.

Take the plunge into the clear, blue seas and go diving in search of shipwrecks (and more than one downed aircraft!) or stay above the surface and do a bit of windsurfing. Swim, snorkel, or just lie on the beach: how you spend your Aruba vacation is up to you. After all, you’ve saved money on the flights, so treat yourself!

Monterrey, Mexico from Laredo

Although Monterrey has a more modern vibe, the Barrio Antiguo takes you back to the past with it's colorful houses Although Monterrey has a more modern vibe, the Barrio Antiguo takes you back to the past with it’s colorful houses — Shutterstock

One of Mexico’s most modern and forward-looking cities, Monterrey has spent the last few years welcoming startups and tech giants alike and evolving into a city that has everything a young, dynamic place needs.

Surrounded by mountains, thus giving it a spectacular natural backdrop, the center of the city has a lot of modern architecture plus repurposed industrial spaces, as well as Barrio Antiguo, a cobbled, colonial area now home to chic artisan stores, quirky bars, and coffee shops. The museums give a generous and detailed history of the city and region while heading out into the wild scenery gives the adventurous among you the chance to climb, mountain bike, hike, abseil — even hang-glide!

Cartagena, Colombia from Fort Lauderdale

View to San Pedro Claver church in Cartagena de Indias, Colombia View to San Pedro Claver church in Cartagena de Indias, Colombia — Shutterstock

With a fascinating history dating back to the 16th century, miles of beaches, color, a tropical climate and a spirited personality, Cartagena is a fantastic city to visit all year round. The walled Old City has been a Unesco site since 1984, while the modern skyscrapers across the bay tell of a place its residents are proud to see moving to the future.

Anywhere that’s a popular destination for travelers from that country is always a good sign, and Cartagena is just that, attracting Colombian holidaymakers looking for a spot on the beach or an adventure on one of the surrounding islands. Take a boat trip to the jungles of Isla Grande or the crystal seas of the Barú peninsula, surrounded by coral reefs and national parks, or stay and walk the streets of the Old City, marveling at its historical wealth and splendor.

Toronto, Canada from New York City

The famous Gooderham building in Downtown Toronto, CanadaThe famous Gooderham building in Downtown Toronto, Canada — Shutterstock

Connecting two of the greatest cities in North America in a couple of hours and less than a hundred dollars, routes from NYC to Toronto are quick and easy. Canada’s biggest city is similar to New York in that it’s home to hundreds of nationalities bringing culture, language, cuisine and traditions together, and mixing them up to create somewhere amazing.

Hungry? From a slice of pizza in Little Italy to a steaming bowl of Vietnamese pho, Japanese fusion, a Persian banquet, or just good, friendly poutine, Toronto has the lot and still has room for seconds. To feed your soul, visit one of the hundreds of world-class museums and galleries, see a classical concert or cram yourself in with 30 other people in a dive bar and catch a band. Walk, cycle, or just sit in one of the many parks and enjoy watching other people expend the effort!

Guayaquil, Ecuador from Pittsburgh

The view from Santa Ana hill in Guayaquil, Ecuador The view from Santa Ana hill in Guayaquil, Ecuador — Shutterstock

Since the turn of the millennium, Guayaquil has set about reinventing itself. Urban renewal and local pride have become the watchwords of these changes, with a city that had a less-than-stellar reputation as somewhere to be avoided while changing planes, now a destination in itself.

You’ll find yourself drawn towards the Malecón Simón Bolívar, the waterfront promenade, and the colorful barrio of Las Peñas. The urban renewal program has added peaceful parks, bustling squares, and contributed to making it a center for theater and arts, helped no doubt by the large student population. This is also the place for all connecting flights to the Galápagos Islands, so whether you’re staying or passing through, it’s worth your time now more than ever.

Calgary, Canada from Seattle

Moraine lake in the Calgary Banff national park in the Rocky Mountains, Canada Moraine lake in the Calgary Banff national park in the Rocky Mountains, Canada — Shutterstock

Amiable, friendly, and only an hour’s drive from the edge of the Rockies, Calgary still has the air of a frontier town, but one that’s managing to merge its plaid-and-pickup truck reputation into something a little different. The Calgary Stampede, a ten-day yee-haw fest in July is still a huge draw for the city, but what else is going on?

Well, its foodie reputation is on the up-and-up, as is its craft brewery scene. Similar to another former frontier city, Denver, it’s relying more and more on lively neighborhoods, local art and music, good nightlife, and being just that little bit unknown, meaning it feels like you’ve discovered somewhere the rest of the world hasn’t quite worked out yet. Pretty cool, right?

So there you have it!

That’s just a glimpse into the thousands of deals we have available for you. Why not download the Kiwi.com app? Search, book, and customize any trip, keep all your travel documents in one place, get access to our Customer Support, or set up price alerts on journeys you’d like to take – we’ll just ping you when the price comes down far enough. Kiwi.com: we hack the system, you fly for less.

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