All Ages

9 Cheapest Places to Fly in Summer 2019

Even though summer is peak travel time for many destinations and airports, there are some surprising airfare deals to be found for summer 2019. We turned to Tracy Stewart, content editor at our sister site, Airfarewatchdog, to find out which destinations are often cheaper to reach during the summer months.

“From pretty much any major U.S. city, flights to Florida are plentiful and relatively inexpensive, even in the summer months,” Stewart says. “Keep an eye out for weekly sales from JetBlue and Southwest for peak summer dates. And remember that even if Southwest is higher by a couple of bucks, it still allows for two free bags per ticket, which could make a huge (price) difference for a family traveling together.”

These are the cheapest places to fly this summer.

Barcelo Maya Beach Resort in Cancun; Courtesy of Barcelo Maya Beach

1. Cancun, Mexico

With nonstop flights to Cancun from most major U.S. cities, the popular Yucatan resort destination is one of those places where you can almost always find an airfare deal.  “The lowest fare tends to hover below $300 round-trip from the East Coast and Midwest,” says Stewart, who suggests checking flights on budget carriers that fly to Cancun, including Volaris, Interjet and VivaAerobus. Once there, you can choose to go as budget or high-end on your stay as you please. Cancun is known for its beautiful turquoise waters, white-sand beaches, and an abundance of all-inclusive resorts.

Recommended Hotel: Barcelo Maya Beach

Kids at Secret Harbour Beach Resort in St. Thomas; Courtesy of Secret Harbour Beach Resort

2. St. Thomas

Jetblue often offers cut-rate fares to St. Thomas in the U.S. Virgin Islands, where you can fly in for far cheaper airfare than Beef Island on Tortola in the BVI (a popular launch point for family catamaran vacations with The Moorings). Many other carriers service St. Thomas from the mainland U.S., too, including United Airlines and American Airlines. Bonus: You don’t need a passport to get to St. Thomas!

Recommended Hotel: Secret Harbour Beach Resort

Lake Eola in Orlando at Night; Courtesy of Visit Orlando

3. Orlando 

Hitting the Disney theme parks at the height of the summer travel season—and the height of Florida’s heat and humidity—may seem like a recipe for disaster. But keep in mind that Central Florida offers much more than just roller coasters, from pedaling a swan boat around Lake Eola in downtown Orlando to going for a refreshing dip at Wekiwa Springs State Park. When looking for flights into Orlando, says Stewart, “Check lesser-known budget carriers like Allegiant that service smaller cities or secondary airports like Orlando Sanford.” That airport is east of downtown Orlando, less than an hour from Daytona Beach, and about a 45-minute drive from most of the area’s theme parks.

Recommended Hotel: The Grove Resort Orlando

Wyndham Grand Rio Mar Puerto Rico Golf & Beach Resort; Courtesy of Wyndham Grand Rio Mar Puerto Rico Golf & Beach Resort

4. San Juan, Puerto Rico 

Recovering from Hurricanes Maria and Irma has been an ongoing process for Puerto Rico, but vacationers are heading back to enjoy the U.S. island’s beauty. You can feel the energy of the locals’ motivation to rebuild what was destroyed during the storms, with many of the island’s iconic hotels operating again. Fly into San Juan and be on the beach at the resorts of Isla Verde and Condado within minutes, or out exploring the historic streets of the old town of San Juan.

Recommended Hotel: Wyndham Grand Rio Mar Puerto Rico Golf & Beach Resort

Pool at Hilton Fort Lauderdale Beach Resort; Courtesy of Hilton Fort Lauderdale Beach Resort

5. Fort Lauderdale

Jetblue and Spirit Airlines are good carriers to keep an eye on if you’re looking for affordable flights into Fort Lauderdale this summer. And whether you’re planning to vacation in Fort Lauderdale itself or rent a car and head farther afield to explore the nearby Everglades or Miami Beach to the south, flying to Fort Lauderdale gives you easy access to all the highlights of South Florida.

Recommended Hotel: Hilton Fort Lauderdale Beach Resort

Water Sports at Crystal Cove by Elegant Hotels; Courtesy of Crystal Cove by Elegant Hotels

6. Barbados 

With some of the best pubic beaches in the Caribbean, good all-inclusive resort options, as well as independent hotels and authentic British flair, Barbados makes for a fun and exotic family vacation to the Caribbean. Summer’s hurricane season means flights are often discounted, and if you check Jetblue’s deals, you can often score an airfare surprise. Once here, there’s all kind of history and culture to explore with your gang, in addition to the simple pleasures of playing on the beach. On Friday and Saturday nights in particular, Bajans love a good fish fry. Plan an evening with the family at Oistins, a working-class fishing village south of Bridgetown that hosts one of the best fish frys island-wide.

Recommended Hotel: Crystal Cove by Elegant Hotels

Compass Point Beach Resort in Nassau, Bahamas; Courtesy of Compass Point Beach Resort

7. Nassau, Bahamas 

Consistently one of the most inexpensive Caribbean destinations to fly to from the U.S., Nassau often has deals from airports in Florida and elsewhere that are particularly cost-friendly during the summer months. Baha Mar has been getting all the hype of late, with properties like the Grand Hyatt Baha Mar and Rosewood Baha Mar already fast family vacation favorites. To get away from the mass resort complexes of there and Atlantis Resort, consider a more rustic-chic stay at Compass Point Beach Resort, where a collection of colorful wooden bungalows (some perched high on stilts) front a pretty cove next to the long stretch of sand at Love Beach.

Recommended Hotel: Compass Point Beach Resort

Kids at Beaches Turks and Caicos; Courtesy of Beaches Turks and Caicos

8. Turks & Caicos 

Spend your summer vacation snorkeling and kayaking with the kiddos along some of the prettiest beaches in the Caribbean when you score inexpensive airfare to Turks and Caicos, just south of the Bahamas in the Caribbean. American Airlines, Jetblue and Delta usually have fares for under $300 from Florida and just a bit higher from New York (and even Midwest and West Coast cities like Los Angeles, too). Resorts with kids’ programs and tons of water sport offerings abound.

Recommended Hotel: Beaches Turks and Caicos

Bermuda; Courtesy of Just dance/

9. Bermuda

Bermuda is located to the north of the Caribbean, roughly 2.5 hours flying time from East Coast destinations like New York. And according to Stewart, flights to Hamilton (Bermuda’s capital) from New York City,  “are always reliably cheap, in the low $200s, sometimes even below $200, and often available for very last minute getaways.” And while Bermuda isn’t technically in the Caribbean, during the summer and fall months, the temperatures are tropical here, and all of the pastel-colored buildings and homes sure make you feel like you’re in the Caribbean.

Recommended Hotel: The Fairmont Southampton