Plan an exciting vacation without spending an arm and a leg.BY SKYE SHERMAN AND CLAIRE TRAGESER UPDATED JANUARY 19, 2021

Blue waters and palm tree lined beaches in Cozumel, Mexico


Editor’s Note: Those who choose to travel are strongly encouraged to check local government restrictions, rules, and safety measures related to COVID-19 and take personal comfort levels and health conditions into consideration before departure.

For an easy way to spend less and see a lot, hack your travels by the calendar: You can still visit once-in-a-lifetime destinations, but do it at the optimal time, and you’ll save loads.

If there’s a destination on your bucket list that’s just out of your budget, you might be able to book that trip for less than you think, depending on the time of year you visit. For example, go to Japan in the winter, not during cherry blossom season, to save a few bucks. Or, visit Hawaii during the shoulder season to enjoy warm weather without paying peak prices.

By traveling strategically, you can save hundreds (or even thousands) on your dream trip. Kayak, one of the world’s leading travel search engines, shared with Travel + Leisure a list of destinations seeing some of the best deals and biggest year-over-year price drops, broken down by month so you can plan accordingly. The cost indicates the average prices for both round-trip and one-way flights to these destinations, contrasting this year’s fares with those in 2020.

Related: The 50 Best Places to Travel in 2021

These are the cheapest places to travel for each month of the year. All destinations are currently open to Americans, and have at least 1,000 searches, according to Kayak.

January: Telluride, Colorado

Resort ski lift in Telluride, Colorado during winter


Head to Telluride in January, and you can expect to see airfare at a 49% reduction from last year, according to Kayak, with the cost around $768 instead of $1,514. Likely due to a post-holiday dip and colder weather, this downward trend means you can take the money you save and use it on the slopes: January is a great time to ski, snowboard, and shred mounds of fresh powder.

February: Miami, Florida

Aerial view of the art deco buildings on Ocean Drive, the Lummus Park and the beach of South Beach.


Prices in Miami are trending 52% lower in February, dropping from $276 in 2020 to $132 in 2021. Miami is also one of the cities seeing the biggest price drops, according to Kayak. However, winter is prime time in South Florida — it’s one of the few times of year you can count on cool temperatures with plenty of sunshine. You may not want to spend all your time on South Beach during a February visit, but it’s the perfect time to explore outdoors without breaking a sweat: Plan a day walking around Wynwood Walls or exploring the manicured grounds of Vizcaya Museum and Gardens. 

March: Cozumel, Mexico

Blue waters and palm tree lined beaches in Cozumel, Mexico


Head to Cozumel in March for around $388 instead of $573 — a 32% reduction in the average prices of both round-trip and one-way flights. You can still enjoy the beautiful beaches of the Mexican island, since the average temperature sees a high of 82 degrees, but it’s less humid and there’s no threat of hurricanes. It’s also a good time to dive the colorful Mesoamerican Reef, with a good chance of seeing migrating eagle rays up close.

April, July, November, and December: Cancun, Mexico

A general view from one of the accesses to the beach area with palapa umbrellas in Cancun, Quintana Roo State, Mexico, on February 16, 2019


Cancun seems to be the place to be in 2021 for those interested in scoring a deal. In April, you’ll find average airfare to the Mexican city for around $328 instead of $509, which is 36% lower than last year. It’s the driest month of the year, yet it remains warm and sunny and sits right at the end of Cancun’s peak season, so you can expect picture-perfect weather and lower-than-normal prices on flights and hotels

July is another great time to visit Cancun: Kayak reports a 24% price drop for July, from $476 as the average cost in 2020 to $363 in 2021. It’s peak summer this time of year, so expect hot temperatures and picture-perfect beach days

Another low-price month to visit Cancun, November 2021 is trending toward approximately $408 — a 40% reduction in price compared to 2020, when the average cost was $677. The weather during this time of year remains hot enough for beach days, but the humidity is lower and rainy days are less frequent, especially later in the month. It’s a great time to explore Mayan ruins, too. 

Finally, while the airfare in December 2020 hovered around $971, the price for the same time in 2021 is predicted to be about a third of that, at $334. This marks a 66% cost reduction year over year. 

May: Jackson, Wyoming

A bull moose in Grand Teton National Park, Wyoming.


There are few better places to enjoy the great outdoors than the wide-open spaces of Jackson, Wyoming, especially just before the arrival of summer. Kayak reports a 31% price drop in May, from $532 in 2020 to $368 in 2021. On top of the lower prices, visitors can enjoy the invigorating energy of a Wyoming spring as wildflowers begin to bloom, wildlife emerges from hibernation, and snow melts into scenic, winding rivers. Even better, the summer tourist crowds have not yet rushed in.

June: San Juan, Puerto Rico

Colorful buildings in Old San Juan, Puerto Rico


San Juan, Puerto Rico, is predicted to offer 31% lower prices in June, from $393 to $270 in 2021. It’s a great time to pay a visit to the tropical island: The weather is hot, yes, but rainy season hasn’t yet arrived and hurricanes remain unlikely. Wander the cobblestone streets of Old San Juan or take a day trip to El Yunque National Forest to experience the beauty of this picturesque U.S. territory.

August: Dallas, Texas

Margaret Hunt Hill Bridge with Downtown Dallas skyline at sunrise in Dallas, Texas.


Summer in Texas is a scorcher, but it’s the perfect time of year to indulge in mouthwatering BBQ, and no place does that better than the Lone Star State. Head to Dallas in August and enjoy a trip at a 43% lower cost than you would have in 2020 ($179 versus $312). Cool down with a tall glass of ice-cold sweet tea or a tart and refreshing margarita.

September: Washington, D.C.

U.S. Capitol Building seen through autumn leaves in Washington, D.C.


Visiting Washington, D.C. this September should set you back around $205 in airfare — a major difference from the average price of $355 in 2020. Fortunately, September is one of the best months to visit our nation’s capital: Autumn promises milder temperatures, cool breezes, and the exodus of high-season tourists, as well as gorgeous fall scenes as the leaves begin to change. During this time of year, you can comfortably experience both the outdoor monuments and indoor museums. 

October: Denver, Colorado

Autumn leaves and lake front with skyline and mountains in the distance in Denver, Colorado.


Head to Denver in October for about $204, which is 42% lower than last year’s average airfare price of $350. October falls in Denver’s shoulder season, after the summer crowds have left, but before the hordes of winter tourists arrive. Temperatures are likely to be cold, but the weather is dry and sunny, and fall in Denver is beautifully autumnal, so it’s a great month to plan a visit (and the price is right).BY SKYE SHERMAN AND CLAIRE TRAGESER