How to Find All-Inclusive Vacation Packages With Airfare Under $500

Caroline Morse Teel is the Managing Editor for SmarterTravel Media. Follow her adventures around the world on Instagram @TravelWithCaroline.

See recent posts by Caroline Morse Teel

With inflation on the rise, it can feel impossible to get out of the grocery store for under a few hundred bucks, let alone book an all-inclusive vacation package—with airfare—for less than $500.

Fortunately, if you know where to look, there are actually plenty of vacation packages under $500 available that include food, drinks, hotel, and even flights. Follow these tips to find an ultra-cheap vacation deal.

Book Early (Or Last-Minute)

Person using a smartphone and laptop to book a hotel room — Pixel-Shot | Adobe Stock

When it comes to booking an all-inclusive vacation package, you’ll find the best deals if you either book early or at the last-minute. Many resorts will offer early booking bonuses to entice vacationers into locking in plans. Flights will also be cheaper the earlier in advance you book.

At the other end of the spectrum, all-inclusive resorts will generally slash rates in an effort to fill unsold rooms the closer it gets to an arrival date. If you can be flexible, you can find some amazing last-minute deals a week or two before departure.

The Best Sites for Finding All-Inclusive Vacation Packages With Airfare Under $500

There are a number of all-inclusive vacation websites that have sections showcasing deals under $500, making them a great place to start your search. Here are a few of our favorites:

Expedia Vacations Under $500
Cheap Caribbean Vacation Deals Under $599 (You can set your price range on this page to be under $500)
Orbitz Vacation Packages Under $499

Don’t forget to check out our round-up of the best all-inclusive vacation packages with airfare under $500 here as well.

Check Discount Travel Sites

Sign up for emails from Groupon and Travelzoo (or just check their websites weekly), as both discount sites frequently feature all-inclusive vacation packages with airfare for under $500.

Groupon has an air-inclusive trips section on its site that at the time of writing promoted a Hawaii vacation with air for $499 and a Bogota vacation with air for $399.

Likewise, Travelzoo’s Top 20 weekly deals recently featured a $499 Los Cabos vacation deal that included meals, drinks, and flights.

Search in Popular All-Inclusive Destinations

Senior couple relaxing together by the pool at a hotel on a sunny day — maryviolet | Adobe Stock

Mexico, the Caribbean, and Central America are usually the cheapest destinations for all-inclusive packages and a good starting point for your search.

These destinations usually have inexpensive airfare from the United States (especially if you live in the south) and all-inclusive resorts that tend to be reasonably priced as well.

Most all-inclusive resort chains frequently run sales throughout the year. You’ll often see discounted vacation packages for under $500, or even deals which throw in the airfare for free.

The best way to stay on top of these discounts is to sign up for emails—or follow the brands on social media—from the resort chains.

Some of the best all-inclusive resort brands to start with are:

Google Explore + SmarterTravel Hotels

Close up of person's hands as they type on a laptop — Rostislav Sedlacek | Adobe Stock

Sometimes, putting together an all-inclusive vacation on your own can be cheaper than buying a package deal. Use Google Explore to find inexpensive flights from your home airport to anywhere in the world, and then scan SmarterTravel Hotels (SmarterTravel’s sister site) to score a great price on an all-inclusive resort.

Travel in the Off-Season

You’ll have the best luck finding all-inclusive vacation packages with airfare for under $500 if you can travel off-peak. This means avoiding the spring break period at all cost, and instead traveling in May through November if you’re headed to popular destinations in Central America.

You Might Also Like:

• Flight Price Trackers: 6 Sites That Will Find the Cheapest Airfare for You
• The Best All-Inclusive Vacations Under $500, Including Airfare
• The 8 Best Travel Package Sites for Booking a Cheap Vacation
• The 14 Best Flight Search Sites for Booking Cheap Airfare
• Best Websites to Book a Last Minute Vacation

We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.