May is the sweet spot for travel—perfect weather, smaller crowds, and flight deals that won’t drain your wallet. Whether you’re craving a beach escape, a cultural city break, or an epic outdoor adventure, now’s the time to book. From Europe to the Caribbean and beyond, here are the 12 cheapest places to fly to in May 2025. Let’s go.
#1 tip for finding cheap flights in May
Looking to save 50% on airfare this May? This is a game-changer: Going (formerly Scott’s Cheap Flights). Here’s all you gotta do: Sign up for free email alerts, set your departure and destination, and boom – you’ll get alerts for insanely cheap flights. Mistake fares? Deep discounts? They’ve got it all.
I’ve saved thousands using Going. Recently, I even found a $315 roundtrip fare from Boston to Barcelona in May. Not a bad long weekend break if you ask me!
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1. Santorini, Greece ($410–$540 roundtrip)
- 🛫 Airlines: Delta, Turkish Airlines, Emirates (usually nonstop or with 1 stop)
- 🔥 Perfect for: Island dreamers, sunset chasers, white-and-blue aesthetic lovers, honeymooners
Santorini ranks among the amazingly cheapest places to fly in May when airlines drop prices right before peak summer season hits. The island delivers those iconic white buildings with blue domes without the insane crowds or prices of July and August.
Oia is where you’ll find those classic postcard views of white buildings cascading down volcanic cliffs, with the best sunset spots that aren’t completely packed yet in May. The black sand beaches of Perissa and Kamari are warm enough for swimming but not overrun with tourists. Take the hiking trail from Fira to Oia for ridiculous caldera views the whole way, or visit the ancient ruins of Akrotiri (basically the Greek Pompeii) without the summer lines and heat.
When it comes to flights, Turkish Airlines and Emirates frequently offer the best connecting deals through Istanbul or Dubai, with fares sometimes dropping below $450 roundtrip from major US cities when booked 8-10 weeks ahead. Delta partners with European carriers for competitive options through Athens.
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2. Grand Cayman, Cayman Islands ($320–$450 roundtrip)
- 🛫 Airlines: Cayman Airways, American, JetBlue (usually nonstop or with 1 stop)
- 🔥 Perfect for: Beach lovers, snorkeling enthusiasts, stingray selfie seekers, luxury-for-less travelers
Grand Cayman is surprisingly cheap to fly to in May when winter crowds leave but the perfect weather sticks around. The island offers some of the clearest water in the Caribbean without the premium prices of winter high season.
Seven Mile Beach lives up to the hype with perfect white sand and crystal water that’s so clear you can see fish without even snorkeling. Stingray City is that famous sandbar where you can literally stand in waist-deep water while friendly stingrays swim all around you. The Cayman Crystal Caves are super cool limestone formations you can explore without the usual crowds, while Rum Point gives you that laid-back beach bar vibe with hammocks hanging between palm trees.
Cayman Airways often runs direct flight deals from Miami, New York, and Chicago with fares dipping below $350 roundtrip when booked 6-8 weeks ahead. American offers the most connections through Miami but typically charges about $30-50 more than Cayman Airways for similar routes.
3. Costa Rica, Central America ($280–$390 roundtrip)
- 🛫 Airlines: Spirit, JetBlue, United (usually nonstop or with 1 stop)
- 🔥 Perfect for: Nature lovers, adventure seekers, wildlife spotters, jungle explorers
Costa Rica delivers ridiculous biodiversity and adventure for crazy cheap flights in May, right at the start of green season when prices drop but the rain isn’t constant yet. The country packs rainforests, volcanoes, and perfect beaches into an area the size of West Virginia.
Arenal Volcano area is adventure central with zip lines, hanging bridges, and natural hot springs surrounded by jungle. The beaches of Manuel Antonio let you spot monkeys and sloths on jungle trails that literally end at perfect white sand beaches. Monteverde Cloud Forest has that mystical foggy vibe where you can hike through the clouds and spot rare birds and wildlife. Don’t miss Rio Celeste waterfall with its surreal blue water that looks photoshopped but is actually natural minerals.
May marks the beginning of green season with occasional afternoon showers but plenty of sunny mornings and significantly discounted hotels and tours. For flights, Spirit consistently offers the rock-bottom prices, with fares frequently dipping below $300 roundtrip from Florida hubs when you book 6-8 weeks ahead. JetBlue provides a more comfortable experience with competitive pricing from their East Coast hubs.
4. New Orleans, Louisiana, USA ($140–$220 roundtrip)
- 🛫 Airlines: Spirit, Southwest, Delta (usually nonstop or with 1 stop)
- 🔥 Perfect for: Food enthusiasts, music lovers, history buffs, party people
New Orleans is basically perfect in May when flight deals drop after Jazz Fest but the weather is still amazing before summer’s brutal humidity. The city gives you that incredible mix of food, music, and culture without the chaos or prices of Mardi Gras season.
The French Quarter is packed with historic buildings, live music venues, and restaurants serving legit Cajun and Creole food that’ll blow your mind. Frenchmen Street is where locals actually go for the best jazz and blues without tourist prices, while the Garden District lets you explore stunning mansions and above-ground cemeteries on tree-lined streets. May brings comfortable temperatures around 80°F before summer’s oppressive humidity and hurricane season kick in.
Southwest and Spirit frequently battle for the lowest fares, with prices often dropping below $160 roundtrip from major US cities when you book 6-8 weeks ahead. Delta offers competitive pricing from their hub cities.
- Read Next: Cheapest Flights from New Orleans
5. Istanbul, Turkey ($350–$470 roundtrip)
- 🛫 Airlines: Turkish Airlines, United, Delta (usually nonstop or with 1 stop)
- 🔥 Perfect for: History buffs, food enthusiasts, bazaar shoppers, east-meets-west explorers
Istanbul hits the perfect balance in May with shockingly affordable flights to this city that literally straddles two continents. The city delivers a mind-blowing mix of ancient history and buzzing modern culture without the summer tourist hordes.
Hagia Sophia and the Blue Mosque face each other across a plaza in a serious architectural showdown, while the nearby Grand Bazaar has over 4,000 shops where you can haggle for everything from Turkish carpets to silver jewelry. Take a ferry across the Bosphorus for the best city views and to say you’ve literally crossed from Europe to Asia in 20 minutes. Galata Tower area is packed with cool rooftop bars and restaurants where you can feast on amazing Turkish food with panoramic views for a fraction of what you’d pay in other European capitals. Explore these in May when perfect temperatures hover around 70°F.
Turkish Airlines dominates this route with direct flights and frequently runs sales with fares dipping below $400 roundtrip from major US hubs when booked 8-10 weeks ahead. United and Delta offer competitive connecting options through their European partners.
6. Cancun, Mexico ($210–$310 roundtrip)
- 🛫 Airlines: Spirit, JetBlue, Southwest (usually nonstop or with 1 stop)
- 🔥 Perfect for: Beach lovers, cenote explorers, party people, Mayan ruin chasers
Cancun is ridiculously affordable in May when winter crowds disappear but hurricane season hasn’t started yet. The city gives you that perfect combo of Caribbean beaches and Mayan culture without the spring break chaos or holiday price gouging.
Playa Norte on nearby Isla Mujeres has that powdery white sand and crystal clear water that looks fake but isn’t, accessible by a quick ferry from downtown. The Underwater Museum of Art lets you snorkel among hundreds of submerged sculptures creating an artificial reef that’s both cool and good for the environment. Don’t miss day trips to Chichen Itza to see those famous Mayan pyramids or swimming in cenotes (natural limestone sinkholes) with water so blue it doesn’t seem real. Tulum offers those Instagram-worthy beach ruins if you’re willing to venture a bit further south.
Spirit consistently offers the absolute rock-bottom fares, with prices frequently dipping below $230 roundtrip from major US cities when you book 6-8 weeks ahead. JetBlue and Southwest provide better flying experiences with competitive pricing.
7. Lisbon, Portugal ($300–$430 roundtrip)
- 🛫 Airlines: TAP Air Portugal, United, Delta (usually nonstop or with 1 stop)
- 🔥 Perfect for: Hill wanderers, tile admirers, pastry addicts, budget European explorers
Lisbon is Europe’s best-kept secret in May when transatlantic flight deals make this gorgeous city totally affordable. The city is basically Europe with a beach vibe, offering incredible food, stunning views, and perfect spring weather without Barcelona or Paris prices.
Alfama district is a maze of narrow streets and colorful buildings where old ladies hang laundry from balconies and tiny hidden bars play traditional Fado music. The famous yellow Tram 28 rattles up and down hills through the most photogenic parts of the city for just a few euros. Time Out Market lets you sample food from the city’s best chefs all under one roof, while the Pastéis de Belém bakery serves those famous custard tarts that are seriously addictive. For the best views, climb to São Jorge Castle or take the Santa Justa Elevator for panoramas across the city’s red rooftops.
TAP Air Portugal consistently offers the best direct flight deals, with prices frequently dipping below $350 roundtrip from Boston and New York when you book 8-10 weeks ahead. The airline often runs “Portugal Stopover” promotions letting you visit two cities for the price of one.
8. Vancouver, Canada ($190–$270 roundtrip)
- 🛫 Airlines: Air Canada, Alaska Airlines, United (usually nonstop or with 1 stop)
- 🔥 Perfect for: Outdoor enthusiasts, food lovers, city explorers, nature photographers
Vancouver is ridiculously gorgeous in May when flight deals are still low but the weather starts getting amazing. The city hits that perfect balance between urban cool and easy access to mountains, forests, and ocean all in one trip.
Stanley Park is the massive urban forest with a 5.5-mile seawall path where you can bike or walk with ocean on one side and towering trees on the other. Granville Island market is food heaven where you can sample everything from fresh seafood to artisanal cheese before hopping on a tiny Aquabus to cross the harbor. Gastown has those cool indie shops and the famous steam clock that tourists always photograph, while a quick drive up to Grouse Mountain gives you insane views of the entire city spread out below.
Alaska Airlines and Air Canada frequently battle for the best deals, with fares often dropping below $220 roundtrip from West Coast cities when you book 6-8 weeks ahead. United typically matches these prices from their hub cities.
9. Cartagena, Colombia ($240–$360 roundtrip)
- 🛫 Airlines: Spirit, JetBlue, Avianca (usually nonstop or with 1 stop)
- 🔥 Perfect for: Beach lovers, history buffs, food enthusiasts, colorful photo seekers
Cartagena serves up Caribbean vibes with Latin flavor at prices that’ll make your wallet happy in May. The city lets you explore a UNESCO-listed walled city, hit gorgeous beaches, and experience Colombian culture without South Beach prices.
The Walled City (Old Town) looks straight out of a movie set with colorful colonial buildings, flower-covered balconies, and street performers on every corner. Getsemaní neighborhood nearby has killer street art and local vibes where you can grab cheap beers and dance salsa with actual Colombians. Take a boat trip to the Rosario Islands for ridiculous clear water and white sand beaches that blow away the city beaches, or climb La Popa Monastery hill for the best sunset views over the entire city.
May hits that perfect window right before rainy season really kicks in, with temps around 85°F and slightly lower humidity than other months. Flight-wise, Spirit consistently offers rock-bottom prices, with fares frequently dipping below $260 roundtrip from Fort Lauderdale and Orlando when you book 6-8 weeks ahead. JetBlue and Avianca provide better service with competitive pricing from their hub cities.
10. Bariloche, Argentina ($490–$630 roundtrip)
- 🛫 Airlines: Aerolíneas Argentinas, LATAM, American (usually nonstop or with 1 stop)
- 🔥 Perfect for: Mountain lovers, chocolate enthusiasts, lake adventurers, off-season explorers
Bariloche is basically South America’s hidden gem in May when flight deals make this Patagonian paradise surprisingly affordable. The city gives you that perfect mix of Swiss-style mountain vibes and Argentine culture right as fall colors hit their peak.
Cerro Catedral offers ridiculous mountain views without needing to hike (take the cable car up), while the Circuito Chico drive lets you hit multiple viewpoints of crystal blue lakes surrounded by snow-capped peaks. The downtown area looks like a Swiss village with Alpine-style buildings and chocolate shops on every corner (seriously, the chocolate here is legendary). Nahuel Huapi Lake has that perfect mirror-like water reflecting mountains, and you can take boat trips to islands or just chill on the shore with a mate tea like the locals do.
May marks the start of shoulder season with temperatures around 45-55°F, perfect sweater weather with gorgeous fall foliage but before winter tourism kicks in for skiing. LATAM and Aerolíneas Argentinas typically offer the best connecting deals through Buenos Aires, with fares sometimes dropping below $550 roundtrip from Miami when booked 10-12 weeks ahead. American provides competitive options through their South American partners.
11. Tokyo, Japan ($460–$650 roundtrip)
- 🛫 Airlines: ANA, Japan Airlines, United (usually nonstop or with 1 stop)
- 🔥 Perfect for: Culture enthusiasts, food lovers, tech geeks, spring explorers
Tokyo hits a perfect travel window in May with flight deals that make this bucket-list city actually affordable. The city offers that mind-blowing mix of ancient temples and futuristic technology without the crowds of cherry blossom season or summer tourism.
Shibuya Crossing gives you that classic Tokyo experience where thousands of people cross at once in perfect organized chaos, while nearby Yoyogi Park hosts weekend gatherings of cosplayers, rockabilly dancers, and other uniquely Japanese subcultures. Senso-ji Temple in Asakusa offers traditional vibes with its massive red lantern and surrounding market streets. Don’t miss the Robot Restaurant in Shinjuku for a completely bonkers show, or Tsukiji Outer Market where you can feast on the freshest sushi for breakfast. For incredible city views, hit the free Tokyo Metropolitan Government Building observation decks instead of paying for Tokyo Skytree.
ANA and Japan Airlines frequently offer competitive direct flight deals, with prices occasionally dipping below $500 roundtrip from West Coast hubs when you book 10-12 weeks ahead for midweek travel. United typically matches these prices through their partnership with ANA.
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12. San Antonio, Texas, USA ($130–$210 roundtrip)
- 🛫 Airlines: Southwest, American, United (usually nonstop or with 1 stop)
- 🔥 Perfect for: History buffs, Tex-Mex lovers, river walkers, budget travelers
San Antonio ranks among the cheapest places to fly in May, just right before summer’s brutal heat kicks in. The city gives you that unique blend of Texan and Mexican culture without the tourist crowds of bigger destinations.
The River Walk is literally the coolest urban waterway in America, with restaurants and bars lining both sides of the river that cuts through downtown. The Alamo is smaller than you expect but still worth checking out, and the other historic missions nearby are actually less crowded and super impressive. Market Square is where you’ll find authentic Mexican food and crafts in a massive outdoor market, while Pearl District has transformed from old brewery to hipster food haven with some of the city’s best restaurants and weekend farmers markets.
Southwest consistently offers the best deals with fare sales dropping prices below $150 roundtrip from most major cities when you book 4-6 weeks ahead. American and United typically match these prices from their hub cities.
- Read Next: Cheapest Airports to Fly Into Texas
