10 Cheap Labor Day Weekend Getaways for 2019

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Shorter days, cooler weather, and back-to-school sales are right around the corner—but don’t let summer come to an end without enjoying one last vacation. Book one of these cheap Labor Day weekend getaways to take advantage of low airfares, affordable hotel rates, and special events in a variety of U.S. and international locations.

Cheap Labor Day Weekend Getaways for 2019

Below are the 10 best places to go for Labor Day weekend this year. One tip to keep in mind: For travelers whose dates are flexible, the experts at booking site Cheapflights.com recommend flying out on Saturday, August 31, and returning Tuesday, September 3, for the best prices. Thursday, August 29, is the most expensive day to depart before the long weekend.

Editor’s note: All featured hotels had availability for Labor Day weekend at the time of publication. Thanks to Airfarewatchdog, Cheapflights.com, Booking.com, and CheapOair for data and insight.

Chicago, Illinois

With a median fare of $204 round-trip (per Cheapflights data) and a central location that’s easily reached from most parts of the U.S., Chicago is one of the best Labor Day getaways for travelers looking for an urban escape. There’s a diverse slate of events in the city that weekend, from the Jazz Festival and the African Festival of the Arts to the Great American Lobster Fest at Navy Pier.

Want to catch a game? The Cubs are in town that weekend, playing at historic Wrigley Field. You can also tour the recently restored Robie House, designed by architect Frank Lloyd Wright. For more ideas, see SmarterTravel’s Chicago travel guide.

Puerto Rico

There are two affordable gateways for flights into Puerto Rico—Aguadilla (the median round-trip fare, according to Cheapflights, is $280) and San Juan ($314). Either one gives you access to the island’s beautiful beaches and unique culture. Ricky Radka, Senior Content and Deal Strategist at Airfarewatchdog, SmarterTravel’s sister site, notes that you’ll find particularly reasonable fares from JetBlue strongholds such as Boston, New York, and Fort Lauderdale.

As the island continues to recover from Hurricane Maria, it’s welcoming visitors back to key sites such as El Yunque National Forest, Old San Juan, and the stunning Flamenco Beach. Eating at locally owned restaurants is one way you can support the island’s ongoing recovery—as well as enjoy a fantastic meal. Popular spots include Santaella (for upscale Caribbean cuisine), Caldera Cafe (coffee and light fare), and Cafe El Punto (Latin American dishes).

Americans don’t need to change money or bring a passport because Puerto Rico is part of the U.S.; however, you might want to buy hurricane travel insurance just in case.

Las Vegas, Nevada

There’s never a bad time to visit Las Vegas, and Labor Day weekend is no exception. “Fierce competition amongst low-cost carriers like Sun Country, Spirit, Allegiant, and Frontier in this top leisure market means there are often deals to be had,” notes Radka. “In some instances, you might be able to hit the jackpot with a traditional legacy carrier price matching with one of the no-frills airlines on head-to-head routes. As an example on Sun Country, flights from PDX to LAS on Friday to Monday are tallying in at $222, and from the carrier’s hub in MSP, trips to Vegas are $150 for a Friday to Tuesday itinerary.”

CheapOair lists the city as one of its most affordable Labor Day getaways, with average round-trip fares around $298. A quick search of hotels on TripAdvisor (SmarterTravel’s parent company) turns up numerous options under $150 a night for the holiday weekend, especially if you’re willing to stay off the Strip. Booking.com also has Labor Day hotel deals, starting at $22 a night.

Yes, the weather will likely be hot this time of year, but there are lots of hotel pools where you can cool off—not to mention all the city’s indoor attractions such as shows, shopping, and celebrity chef restaurants. You’ll barely have to leave the air-conditioning.

Ottawa, Canada

Cheapflights lists Ottawa as its most affordable international Labor Day vacation destination, with a median round-trip flight costing just $220. The strength of the U.S. dollar against the Canadian dollar means that Americans will get more for their money when it comes to hotel rates, restaurants, and shopping in the Canadian capital.

You can browse Ottawa’s numerous farmers’ markets, visit museums such as the National Gallery of Canada and the Canadian War Museum, and tour the landmark Parliament buildings. Festivals happening near Ottawa over Labor Day weekend include Joy Fest and Festival de Montgolfieres de Gatineau, which features live music and hot air balloon rides.

Orlando, Florida

You don’t need to pay a fortune to enjoy one last family trip before the kids head back to school. The median Labor Day airfare to Orlando is just $177 round-trip, according to Cheapflights, and Booking.com has gathered special hotel deals for the long weekend.

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In addition to the city’s usual Disney attractions, Epcot’s 2019 International Food & Wine Festival starts August 29 and features global cuisine, chef demonstrations, family activities, and concerts. Access to the festival is included with theme park admission.

Want to spend part of your weekend outside of the Disney empire? There’s plenty to see in Orlando beyond the theme parks, including the Orlando Museum of Art and the Central Florida Zoo & Botanical Gardens.

Mexico City, Mexico

Labor Day weekend may be part of the wet season in Mexico City, but in an urban area with more than 150 museums, you’ll have no problem filling a rainy afternoon. Cheapflights pegs the median round-trip airfare to Mexico City at $308, and the city is bustling with affordable hotel and restaurant options. Radka recommends checking fares on low-cost carrier Interjet, which is offering nonstop Labor Day weekend flights from Dallas, Houston, Miami, Orlando, and Las Vegas from $250 – $320 round-trip. Don’t-miss sites include the 18th-century Chapultepec Castle, the Frida Kahlo Museum, and the Zocalo, one of the world’s largest public squares.

Nervous about traveling to Mexico? Although the U.S. State Department recommends against travel to certain parts of the country, Mexico City is currently rated as a Level 2 for safety—the same rating as France and Italy.

Los Angeles, California

If you want to combine arts, culture, and beach time during your Labor Day getaway, Los Angeles is the place to be—and with a median airfare of $211 round-trip, according to Cheapflights, it won’t break the bank. Booking.com has gathered special Labor Day deals on Los Angeles hotels.

Must-see Los Angeles attractions include everything from the world-class art collection at the Getty Center to the glitzy shops of Rodeo Drive. You can also check out Labor Day weekend events such as the LA County Fair and the Pasadena Daydream Festival, headlined by the Pixies and the Deftones.

St. Lucia

According to Cheapflights data, airfares to St. Lucia have dropped 28 percent since last year, to a current median price of $558 round-trip. Although St. Lucia has numerous high-end resorts, you’ll also find plenty of budget-friendly properties scattered around the island.

St. Lucia is a nature lover’s paradise, with hiking trails, botanical gardens, and even sulfur springs to explore. Or, if you like, you can spend your long weekend simply relaxing on stretches of sand like Anse Chastanet or Anse Cochon. As with Puerto Rico, you might want to buy travel insurance to protect yourself during hurricane season.

Denver, Colorado

Enjoy a Labor Day vacation full of outdoor adventures and mountain views in Denver. The median round-trip flight costs just $206, according to Cheapflights, and there are plenty of cheap or even free things to do in the area, from hiking scenic trails to browsing art galleries and studios in the Golden Triangle Creative District.

There’s a lot going on in Denver over Labor Day, including a beer festival, a music festival, and a fireworks display. The Rockies are also in town if you want to catch a baseball game at Coors Field.

Vancouver, Canada

The cost of living may be a little higher in Vancouver than in the other Canadian city on this list, but it’s still an affordable Labor Day weekend getaway, especially for Americans on the West Coast. (The median round-trip airfare is $317, according to Cheapflights.) Some of the city’s most popular places to visit are inexpensive or free, including Stanley Park and Granville Island Public Market.

Consider making a day trip to nearby Richmond to experience the Richmond World Festival, featuring live music, food trucks, a culinary stage, and cultural workshops.

What to Wear on Your Labor Day Getaway

More from SmarterTravel:

• Cheap Weekend Getaways from 9 Major U.S. Cities
• 7 North American Cities Perfect for a 3-Day Weekend
• The 10 Best U.S. Cities to Visit in 2019

Follow Sarah Schlichter on Twitter @TravelEditor for more travel tips and inspiration.

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