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Memorial Day weekend (May 23–26, 2025) is the unofficial kickoff to summer—and one of the busiest travel periods of the year. But that doesn’t mean you have to break the bank to get away.
With a little research and smart planning, you can still score cheap flights to some awesome destinations.
If you're looking to fly abroad, here are (historically) some of the best cheap places to fly for Memorial Day weekend. Just make sure to install a travel eSIM so you can stay connected on your trip without any nasty roaming bill at the end of it. With Sim Local, you can get one online and install it instantly. Simply choose from 200+ destinations and pick your perfect plan.
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Check out this Mexico plan, or choose one from 200+ destinations
Why go:
A stylish, multicultural city packed with skyline views, buzzing street festivals, waterfront parks, and a food scene that rivals any major city.
What makes it affordable:
Toronto is often one of the cheapest international flights from major U.S. cities like New York, Boston, and Chicago—especially with budget carriers like Porter and Flair Airlines. Plus, the favorable exchange rate means your dollar goes further once you land.
What to do:
Why go:
Lisbon is one of the most budget-friendly capital cities in Western Europe. With its sunny weather, coastal charm, and laid-back café culture, it’s the perfect long weekend escape.
What makes it affordable:
Flights to Lisbon are often among the cheapest transatlantic options—especially from East Coast cities. Accommodations, food, and transport in Portugal tend to be far more affordable than other Western European hotspots like Paris or Rome. Plus, late May is ideal: great weather, lower crowds, and better prices than peak summer.
What to do:
Why go:
Get a taste of Europe without crossing the Atlantic. With French-inspired charm, cobblestone streets, and historic cafés, Montreal is a place that feels both familiar and refreshingly different.
What makes it affordable:
Since Memorial Day isn’t a holiday in Canada, you’ll avoid the usual travel surge. Flights from Northeastern cities like NYC, D.C., and Boston are especially budget-friendly. Hotels tend to have OK prices this time of year, too.
What to do:
Why go:
If your perfect long weekend involves warm sunshine, turquoise water, and tropical cocktails, Cancún is a no-brainer. It’s the perfect mix of beach and budget.
What makes it affordable:
Flight prices often dip in late May, just before the summer travel boom. U.S.-based airlines regularly offer deals on direct flights, and all-inclusive resort packages can make your trip even more cost-effective.
What to do:
If you want to keep it domestic, here are some of the best cheap places to fly for Memorial Day weekend.
Why go:
Chicago is packed with architecture, public parks, and lakefront energy—plus tons of free and cheap things to do.
What makes it affordable:
As a major airline hub, Chicago benefits from a high volume of flight competition, keeping fares low. Hotels often run Memorial Day specials too.
What to do:
Why go:
A city with a rich cultural scene, top-tier food, and lush green spaces—without the price tag of bigger metros.
What makes it affordable:
Thanks to being a Delta hub, Atlanta has a steady stream of affordable flights. It’s also a great option for Southeastern travelers looking for a quick and wallet-friendly trip.
What to do:
Why go:
It may be hot in May, but that means better prices and fewer crowds. If you love wide-open landscapes, red rocks, and desert trails, Phoenix is a unique pick.
What makes it affordable:
Lower demand over Memorial Day weekend keeps flight prices in check. The city is also a great jumping-off point for budget-friendly road trips to Sedona, Flagstaff, or even the Grand Canyon.
What to do:
Why go:
New Orleans delivers on music, food, and soul—and it’s always a vibe over long weekends.
What makes it affordable:
It’s a consistent budget option with cheap flights from most major cities and plenty of mid-range hotel options. Off-season pricing still applies in late May before the summer heat kicks in fully.
What to do:
You don’t have to splurge to enjoy Memorial Day weekend. Whether you're crossing the border to Canada, jetting off to Mexico, or staying stateside, there are plenty of cheap and exciting destinations to choose from. Coming this close to the weekend, you can definitely find a cheap deal if you stay flexible with your dates, and keep an eye out for last-minute deals.
Ready to plan your escape? Your long weekend adventure is only a flight away.
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