12 Cheapest Places to Fly in May (in 2024)

by Flora Backup
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Our guide is packed with the cheapest places to fly in May, offering you a mix of adventure, relaxation, and culture without the hefty price tag. Get ready to explore our top picks for affordable May travel, each with its own unique charm and budget-friendly tips!

May is the sweet spot for savvy travelers looking to stretch their wings without stretching their wallets. As the world blooms in the pre-summer glow, destinations around the globe throw open their doors with deals that beckon the wanderlust in all of us. From the sun-drenched beaches of Cancun to the historic streets of Istanbul, the world is your oyster in May.

Imagine lounging on the powdery sands of Grand Cayman, diving into the rich history of Cairo, or sipping a café in the shadow of Lisbon’s historic towers—all without the peak season crowds. May offers the perfect balance of pleasant weather and reduced prices, making it the ideal time to embark on that dream trip.

So, pack your bags and get ready to explore the world’s treasures. With a diverse mix of destinations, there’s a perfect spot for every traveler this May. Let’s dive into the cheapest places to fly in May and discover the globe’s hidden gems, all while keeping your budget happily intact!

The cheapest places to fly in May right now

#1 tip for finding cheap flights in May

Looking for cheap flights in May? Before diving into all the top cities and airports to fly in May, I want to share a quick tip on how to save money on airfare.

For the past 3 years, I’ve used Scott’s Cheap Flights (now called Going) to get amazing flight deals. All you have to do is enter your home airport and where you want to go, and from there, they’ll send you mistake fares and other ridiculously cheap flight deals. And the coolest part? It’s 100% FREE! In 2023, I’ve saved thousands of dollars from their email alerts. This includes most recently, a $369 roundtrip fare from Boston to Rome.

There’s a free and a premium version – the free one has pretty much everything you’ll need. Though if you’re like me and travel a lot, it’s worth upgrading to the paid version for $49 per year. I recommend signing up for the free trial (you can cancel at any time) to try it for yourself. And if you like it, use my coupon code JON20 to save 20%!

Now without further ado, here are the best flights in May 2024.

1. Santorini, Greece

If you’re looking for a golden month for a dreamy escape to Santorini, May is your best bet. The island’s iconic blue-domed churches and sunsets are less crowded, making everything more intimate and affordable. Santorini in May is a paradise for those seeking beauty on a budget. The weather is warm, perfect for exploring the cobblestone streets of Oia or lounging by the sea.

In May, both flight and hotel prices in Santorini decrease, establishing it as an affordable travel destination.
In May, both flight and hotel prices in Santorini decrease, establishing it as an affordable travel destination.

During the month, the prices for flights and hotels drop, making it one of the cheap places to travel in May. You’ll find competitive rates for some of the island’s top hotels, like the villas at Celestia Grand. Wander around Firá’s winding lanes or enjoy a sunset cruise around the caldera. The Akrotiri Archaeological Site is also less crowded, offering a peaceful exploration of ancient ruins.

For the best deals, fly into Santorini Airport (JTR). Early booking can snag you a great deal, especially mid-week. Eat like a local at tavernas instead of tourist spots and consider renting a bike or ATV for budget-friendly transportation.


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2. Grand Cayman, Cayman Islands

Grand Cayman beckons with its crystal-clear waters and soft sandy beaches, especially in May. It’s one of the must-visit attractions in the Cayman Islands. This month marks the sweet spot between the busy winter season and the start of the summer crowds. It’s one of the cheap destinations in May for beach lovers and sun seekers alike. The weather is just right for dipping into the Caribbean Sea or basking on the famous Seven Mile Beach.

In May, Grand Cayman offers enticing deals, making it an ideal time for budget-conscious travelers.
In May, Grand Cayman offers enticing deals, making it an ideal time for budget-conscious travelers.

May is also a time for deals in Grand Cayman. Hotels and flights are more affordable, leaving you extra cash for adventures. Stingray City is a must-visit in the Caribbean, where you can swim with friendly stingrays in their natural habitat. Diving enthusiasts will love the Kittiwake Shipwreck & Artificial Reef.

Fly into Owen Roberts International Airport (GCM) for the best access to the island. To save money, consider staying in smaller guesthouses or apartments. Local eateries offer delicious meals at a fraction of the cost of tourist spots. Renting a bicycle or using public buses can also cut down on expenses.

3. Costa Rica, Central America

May brings the start of the green season to Costa Rica, making it lush and vibrant. It’s a time when fewer tourists visit, so you’ll find peace and quiet in the rainforests and beaches. This makes it one of the cheap travel in May destinations for nature lovers and adventure seekers. The slight increase in rain brings out the best in the country’s famous biodiversity, perfect for those who love to explore the outdoors.

May marks the beginning of Costa Rica's green season, transforming the landscape into a lush, vibrant haven.
May marks the beginning of Costa Rica’s green season, transforming the landscape into a lush, vibrant haven.

In Costa Rica, you can enjoy lower prices on accommodations and tours. Visit the stunning Manuel Antonio National Park or the Arenal Volcano for a fraction of the peak season cost. The rainforests are alive with wildlife, and the beaches are serene and beautiful in Costa Rica.

To get to Costa Rica, fly into Juan Santamaría International Airport (SJO) for the best deals. Save more by eating at local sodas (small restaurants) and using public transportation. Consider staying in hostels or eco-lodges for an affordable stay. With a bit of planning, Costa Rica offers an affordable, rich experience filled with natural wonders.

4. New Orleans, Louisiana, USA

As May rolls in, New Orleans offers a unique charm. The city’s famous for its vibrant culture and music, and visiting before the summer heat sets in is ideal. It’s known as the cheapest place to fly to in May, especially if you’re looking for a mix of adventure and culture. Enjoy jazz in the French Quarter or a quiet walk through the Garden District.

As the month of May unfolds, New Orleans showcases its unique and captivating charm to visitors.
As the month of May unfolds, New Orleans showcases its unique and captivating charm to visitors.

During May, hotel rates and airfares to New Orleans are more affordable. The city buzzes with festivals and outdoor concerts, many of which are free or low-cost. Enjoy the Creole cuisine at local diners in New Orleans and explore the city’s rich history without the crowds.

Louis Armstrong New Orleans International Airport (MSY) is your gateway to this soulful city and the primary portal to other nearby destinations from New Orleans. To save money, consider staying in a bed and breakfast or a vacation rental. Use the streetcars to get around; they’re cheap and cover most tourist spots. Remember, in New Orleans, the best experiences often come from simply wandering the historic streets and soaking in the lively atmosphere.

5. Istanbul, Turkey

Istanbul in May sees mild weather and fewer crowds. The city, straddling two continents, is alive with color and culture. It’s a time when you can enjoy all the historic sites and vibrant street life of Istanbul without the rush. Istanbul becomes one of the top flight deals in May, offering a rich travel experience for less.

Prices for accommodations and attractions drop before the summer rush. Visit the grand Hagia Sophia or the bustling Grand Bazaar. The Blue Mosque and Topkapi Palace are less crowded, allowing for a more relaxed visit. Enjoy the local cuisine at neighborhood eateries in Istanbul for an authentic and affordable experience.

Fly into Istanbul Airport (IST) for the best access to the city. Save more by using Istanbul’s extensive public transport network. Consider staying in the Sultanahmet area for close proximity to major sites. Walking tours are a great way to see the city and often operate on a pay-what-you-wish basis. Istanbul in May is all about enjoying the grandeur at a leisurely pace and a friendly price.

6. Cancun, Mexico

In May, the spring break crowds have left in Cancun and the summer rush hasn’t begun. This timing makes it perfect for enjoying the beaches and attractions of Cancun without the usual hustle. Cancun stands out as one of the cheap trips in May, especially for beach lovers and those seeking a tropical getaway.

Cancun is a budget-friendly choice in May, particularly appealing to beach lovers and those desiring a tropical escape.
Cancun is a budget-friendly choice in May, particularly appealing to beach lovers and those desiring a tropical escape.

During this month, hotel rates and flight prices are much more wallet-friendly. Explore the stunning Chichén Itzá or relax on the pristine beaches like Playa Delfines. The underwater museum, Museo Subacuático de Arte, offers a unique snorkeling experience.

For the best flight deals to Cancun, fly into Cancun International Airport (CUN). To save on your stay, consider all-inclusive resorts or budget-friendly hotels just outside the Hotel Zone. Local buses are an affordable way to get around. Street food in Cancun is not only cheap but also delicious, offering a true taste of Mexican cuisine.

7. Lisbon, Portugal

May brings mild weather and colorful festivals to Lisbon. The city’s streets come alive with the scent of blooming flowers and the buzz of early summer activities. It’s a time when you can enjoy the historic charm and coastal beauty of Lisbon without the peak season crowds. Lisbon shines as one of the cheap places to fly in May, offering a blend of culture, history, and seaside relaxation.

Lisbon's viewpoints, such as Miradouro da Senhora do Monte, provide stunning views without any admission cost.
Lisbon’s viewpoints, such as Miradouro da Senhora do Monte, provide stunning views without any admission cost.

Hotel and flight deals are plentiful in May. Wander through the Alfama district or take a tram to Belém to see the Jerónimos Monastery and the Tower of Belém. The city’s viewpoints, like Miradouro da Senhora do Monte, offer breathtaking views for free.

Fly into this beautiful Portugal destination via Humberto Delgado Airport (LIS), conveniently located near the city. Save money by staying in guesthouses or budget hotels. Use the city’s efficient public transport to get around. Eating at local tascas (taverns) offers a taste of authentic Portuguese cuisine at a low cost.

8. Vancouver, Canada

Vancouver bursts into bloom in May, offering mild weather and the natural beauty of both city and surrounding landscapes. It’s a month before the rush of summer tourists, making it one of the cheapest places to fly in May. Vancouver’s gardens are vibrant, and the outdoor activities are just beginning to pick up.

One month before the summer tourist rush, Vancouver becomes one of the cheapest places to fly in May
One month before the summer tourist rush, Vancouver becomes one of the cheapest places to fly in May

Take advantage of the lower hotel rates and enjoy Vancouver’s many parks, like Stanley Park or the VanDusen Botanical Garden. The city’s public markets, especially Granville Island, offer fresh food and local crafts at reasonable prices. May is also great for catching a whale-watching tour or exploring the nearby mountains.

Vancouver International Airport (YVR) is the best gateway to Vancouver and the surrounding areas. For savings, consider using public transit, which is extensive and reliable. Eating at food trucks or markets can save money while offering a taste of Vancouver’s diverse culinary scene.

9. Cartagena, Colombia

May is a sweet spot for visiting Cartagena. The city’s colonial charm, vibrant streets, and Caribbean coast are less crowded and more enjoyable. It’s a time when the warm weather complements the cool sea breeze. Cartagena is known as one of the affordable places to travel in May, offering a rich cultural experience and beautiful beaches at a fraction of the cost.

Cartagena is one of the cheapest places to fly in May, offering beautiful beaches with fewer crowds and costs.
Cartagena is one of the cheapest places to fly in May, offering beautiful beaches with fewer crowds and costs.

Enjoy the city’s colorful architecture and historical sites without the long lines. The Castillo de San Felipe de Barajas and the walls of the old city are must-visits. Beaches like Playa Blanca offer relaxation and beauty without the usual crowds.

Rafael Núñez International Airport (CTG) is the most convenient for reaching Cartagena. To save money, stay in guesthouses or boutique hotels in the Getsemani neighborhood. Street food in Cartagena is both delicious and affordable, offering a true taste of the local cuisine. Public buses and walking are the best ways to explore the city on a budget.

10. Bariloche, Argentina

Bariloche in May sees the prelude to winter, offering crisp air and fewer tourists to savor the beauty of this must-see destination in Argentina. The town is nestled in the Argentinian Patagonia, known for its stunning lakes and mountain scenery. It’s a time when you can enjoy the autumn colors in the forests and a peaceful atmosphere. Bariloche is one of the cheap places to go in May for those who love nature and tranquility.

In May, Bariloche sets the stage for winter with refreshing air and a reduced number of tourists.
In May, Bariloche sets the stage for winter with refreshing air and a reduced number of tourists.

Take advantage of the off-season prices for accommodations and activities. Explore the Nahuel Huapi National Park with its breathtaking landscapes. The Circuito Chico is a must for panoramic views of the lakes and mountains. Chocolate shops and local breweries offer a taste of Bariloche without the usual crowds.

The most convenient airport is San Carlos De Bariloche Airport (BRC). To save money, consider renting a cabin or staying in hostels. Local buses are a budget-friendly way to explore the surrounding areas. Eating at local restaurants or cooking your own meals can also help keep costs down.

11. Tokyo, Japan

May is a delightful time to visit Tokyo. The city is fresh and vibrant after the cherry blossom season, with pleasant weather and green parks. It’s a period of festivals and outdoor activities, making the city’s energy infectious. Tokyo is recognized as one of the cheapest places to fly in May due to the dip in travel costs post-Golden Week.

Tokyo is one of the cheapest places to fly in May, with a decrease in travel expenses following Golden Week.
Tokyo is one of the cheapest places to fly in May, with a decrease in travel expenses following Golden Week.

Enjoy the Sumida Park or take a boat ride down the Sumida River for stunning views of Tokyo. The Meiji Shrine and Asakusa district offer cultural experiences without the dense crowds of peak seasons. Street food and markets provide delicious meals at a lower cost.

Tokyo’s most convenient airport is Tokyo Haneda Airport (HND), offering easy access to the city. Its ANA Suite Lounge is renowned for its exceptional service and impressive amenities, making it one of the finest airport lounges in the world. Save money by using the extensive public transportation system and opting for capsule hotels or guesthouses. Convenience stores in Tokyo offer surprisingly tasty and affordable meal options. Exploring the city on foot is not only free but also allows you to catch the subtle beauty of Tokyo’s streets.

12. San Antonio, Texas, USA

In May, San Antonio is alive with cultural events and the weather is warm, perfect for enjoying the famous River Walk or the historic Alamo. With fewer tourists than the summer months, it’s one of the cheapest places to travel in May. The city’s blend of Texan and Mexican cultures offers a unique experience for all visitors.

With fewer tourists compared to the summer months, San Antonio becomes one of the cheapest places to fly in May
With fewer tourists compared to the summer months, San Antonio becomes one of the cheapest places to fly in May

Take advantage of the many free or low-cost historical sites. The San Antonio Missions National Historical Park is a must-see. For a break from the heat, explore the many museums or the cool caverns nearby. Dining in San Antonio is a treat with plenty of affordable Tex-Mex and barbecue options.

San Antonio International Airport (SAT) is the most convenient for reaching Texas and this beautiful city. Consider staying in a bed and breakfast or a budget hotel to save money. Public transportation and walking are great ways to explore the city center. Remember, San Antonio’s charm lies in its relaxed pace and friendly atmosphere, making it a great choice for a budget-friendly May getaway.

Frequently Asked Questions (FAQs) about the Cheapest Places to Fly in May

Got questions on how to save big with cheap travel in May? Our FAQ has all the answers to make your May getaway both memorable and affordable.

Where is the cheapest place to go in May?

The cheapest place to go in May often includes destinations like Southeast Asia or Central America, where the off-peak season leads to lower prices. Places like Vietnam, Thailand, and Costa Rica offer great value. They provide lush landscapes, rich culture, and affordable accommodations. Research specific cities for deals, as prices can vary widely.

Which country is the best time to visit in May?

May is a fantastic time to visit countries with mild spring weather like Italy or Japan. Italy offers pleasant temperatures and fewer crowds before the summer rush. Japan is beautiful post-cherry blossom season with comfortable weather and green landscapes. Both countries offer a mix of outdoor activities and cultural experiences perfect for May travel.

Where to fly cheap in May?

To fly cheap in May, consider destinations that are in their shoulder season like Greece or Portugal. Airfare to places like Santorini or Lisbon tends to be lower. Also, look at flying into major hubs and then taking a regional carrier to your final destination. Always compare prices and consider alternative airports for the best deals.

May is a concealed treasure for travelers seeking exploration without exceeding their budget.
May is a concealed treasure for travelers seeking exploration without exceeding their budget.

Where is the cheapest place to fly in May?

The cheapest place to fly in May can vary each year, but typically includes cities in countries experiencing off-peak tourism. Look for flights to places like Cancun, Mexico, or Istanbul, Turkey. These destinations often have reduced rates on flights and accommodations due to the timing before the busy summer season.

What are the best budget destinations for a May vacation?

For a May vacation, consider places like Vietnam, Bulgaria, or the southern United States. These destinations offer a variety of experiences from beaches to cultural sites, all at a lower cost. The weather is generally favorable, and you’ll find that your money goes further in these areas compared to more popular tourist spots.

How can I save money traveling in May?

To save money traveling in May, book flights and accommodations in advance. Look for destinations in their shoulder season for lower prices. Use public transportation and eat where locals do to save on food. Consider alternative accommodations like hostels or vacation rentals. Always look for free or low-cost attractions to keep entertainment expenses down.

What are some underrated May travel destinations?

Underrated May travel destinations include the Baltic States, Western Canada, and the Appalachian region in the USA. These areas offer beautiful natural landscapes, interesting cultural experiences, and generally fewer tourists. From the historic cities of Latvia to the scenic mountains of Alberta, these destinations provide unique experiences without the high costs or crowds.

Why is May a good month for budget travel?

May is a good month for budget travel because it’s shoulder season in many parts of the world. Prices for flights and accommodations drop after the high season but before the summer rush. The weather is generally mild, making it a great time for outdoor activities and sightseeing without the extreme costs or temperatures of peak seasons.

What are the benefits of traveling in May?

Traveling in May offers the perfect balance of pleasant weather and fewer crowds in many destinations. It’s a time when you can enjoy the beauty of spring or the early whispers of summer with more space and often at a lower cost. From blooming landscapes to vibrant festivals, May travel provides a unique experience that combines the best of both comfort and cost.

Can I find last-minute deals for travel in May?

Yes, last-minute deals for travel in May are often available, especially as hotels and airlines aim to fill up remaining spaces. Keep an eye on travel websites and apps for sudden price drops or special promotions. Being flexible with your destination and dates can increase your chances of snagging a great last-minute deal for a May adventure.

Concluding Thoughts on the Cheapest Places to Fly in May

May is a hidden gem for travelers looking to explore without breaking the bank. It’s the perfect time to catch the tail end of spring or the start of summer in many places around the world. From the beaches of Mexico to the historic streets of Europe, the cheapest places to travel in May are waiting for you.

Embrace the mild weather, fewer crowds, and lower prices. Whether you’re seeking adventure, relaxation, or cultural immersion, May offers a world of possibilities. So pack your bags and get ready to create unforgettable memories, all while keeping your budget happy!

The cheapest places to fly in May for all types of travelers
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