May 2026 Cheap Flights: Here’s Where To Travel For Less Than $600 Round-Trip

Spirit Airlines has officially ended operations. Delta Air Lines announced that flight attendants wouldn’t be serving snacks on flights under 350 miles. Baggage fees are rising, and major airlines have said travelers should continue to expect higher airfares. Every day seems like the Hunger Games, and the one thing we all cling to — vacation — seems like it’s becoming less affordable.

The good news is that not everything is doom and gloom. There are still affordable flights in May that will let you escape, rest, and rejuvenate for less than $600 round-trip. We did the legwork, so all you have to do is click and purchase. Here are the cheapest flights to book this May.

San Juan, Puerto Rico For As Low As $180 Round-Trip

May is the last month before the Atlantic Hurricane Season starts in June. It’s widely considered one of the best times to travel because it falls. within the shoulder season, offering a balance between great weather, reduced costs, and fewer crowds.

Head to Old San Juan first. Wander through the colorful colonial streets (Calle Fortaleza), then visit the historic sites, Castillo San Cristobal and Castillo San Felipe del Morro. Next, venture off to a rum tasting or book a street food tour.

For beaches, relax at Luquillo Beach or Condado Beach, and don’t leave without visiting El Yunque National Forest. As the only tropical rainforest in the U.S. National Forest System, plan for a fun, outdoor adventure filled with hiking trails and waterfalls.

Round-trip flights from Washington, D.C., Fort Lauderdale, Chicago, Miami, Tampa, Orlando, Atlanta, New York City, Philadelphia, and Detroit are available for less than $250 on Skyscanner.  If you’re out west, Denver, Houston, Dallas, and Los Angeles have round-trip flights for less than $325. The cheapest option leaves Jacksonville, Florida.  Use May 14-17 as your travel dates for a round-trip ticket under $180 on Google Flights.

Mexico City, Mexico For As Low As $260 Round-Trip

There’s so much to love about Mexico City. With year-round appeal, it’s rarely a quiet destination. However, May offers that sweet spot of manageable crowds and lower accommodation costs. 

The cheaper flights and hotel costs come with a caveat: it’s one of the warmer months with heavy daily downpours as the season transitions. Still, the days will bring sunshine and enough entertainment that a little bit of rain isn’t worth missing out on a great travel deal.

Architecture tours should be the first thing you do, followed by food tours, shopping at the artisanal market, La Ciudadela, and visiting the iconic Chapultepec Park. Early May often has the final lavender blooms of jacaranda trees, and the May showers begin to turn the city’s parks and surrounding mountains vibrant green.

Round-trip flights from San Antonio, Miami, Las Vegas, Austin, Los Angeles, Dallas, Oakland, and Chicago are less than $300 round-trip on Skyscanner.

Houston is the cheapest option. Use May 16-May 23 as your travel dates on Google Flights to find a round-trip flight for less than $260.

Cartagena, Colombia For As Low As $300 Round-Trip

Another destination that’s perfect for affordability this May is Cartagena, Colombia, where, like San Juan, it tends to be quieter, and costs are lower due to the start of the rainy season.

Start your trip exploring the Walled City (Ciudad Amurallada). This UNESCO World Heritage Site takes you back in time with its 16th-century colonial architecture and historic fortifications.  Highlights of the Walled City include the nearly seven-mile-long stone walls, the iconic Clock Tower, the Gold Museum, the Inquisition Palace, and the Iglesia de San Pedro Claver.

End your night in the Getsemani neighborhood. While it has a reputation for being touristy, it’s a special place that comes to life at night with live music, street parties, and high energy.

Round-trip flights from Fort Lauderdale, Orlando, Durham, Tampa, Atlanta, Chicago, Washington, D.C., and Pittsburgh are all under $400 on Skyscanner. For about $40 more, round-trip flights from Los Angeles and Austin are less than $430.

The cheapest departure city is Miami.  Use May 17-May 23 as your travel dates on Google Flights to find a round-trip ticket for less than $300.

Panama City, Panama For As Low As $300 Round-Trip

If there’s one destination that has continuously made it to our monthly flight deal round-ups, it’s Panama City, Panama.  It may be a sign to join the growing movement of Black Expats who call this vibrant city home.

During your visit, head to the streets of San Felipe, or as locals call it, Casco Viejo. This UNESCO-protected neighborhood is located in the heart of the old city. Tour the colorful, Frank Gehry-designed museum of biodiversity, Biomuseo, then hike up to the city’s highest point on Cerro Ancón for the best views of the city.

Travelers leaving Tampa, New York City, Cleveland, Durham, Atlanta, or Charlotte can find a round-trip flight for less than $500 on Skyscanner.  The cheapest option this May leaves Fort Lauderdale. Use May 25-May 31 as your travel dates on Google Flights for a round-trip for less than $300.

Lima, Peru, For As Low As $475 Round-Trip

In May, it’s autumn in Lima, Peru, where the weather is nothing short of perfect. Pack a light jacket and get ready to explore during this sweet spot before peak travel resumes.

Make plans to visit the Historic Center of Lima and explore the Huaca Pucllana. It’s an ancient pyramid-shaped structure located about 40 minutes south of the city center. Stroll along the Miraflores boardwalk for breathtaking ocean and cliff views. If you’re looking for adventure, you’ll find plenty of opportunities for paragliding here.

Some of the most colorful streets in Lima are in the Barranco neighborhood. You will know exactly when you arrive. Visitors are met with an energetic art scene, galleries, and the Bridge of Sighs.

On Skyscanner, flights are available for under $500 round-trip departing from New York City, Miami, Washington, D.C., Fort Lauderdale, and Austin. Orlando is the cheapest city to travel to Peru. In Google Flights, use May 10-May 16 as your travel dates to find a round-trip ticket for less than $475.

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