30

Every winter, I find myself itching for sun – but not for sky-high airfare or packed resorts. Over the years, I’ve learned that the best winter escapes aren’t necessarily the most obvious ones. Some of the best trips I’ve taken started with a cheap flight alert and a little flexibility.

If you’re wondering where to travel this winter for cheap flights and sunshine, this list is for you. These spots offer warm weather, solid flight deals, and a sense of escape that doesn’t require months of planning or a five-figure budget. A few are tropical, others more cultural, but each one is realistic, refreshing, and very doable…even in the heart of winter.

• ✈️ Pro tip: Want winter flight deals sent straight to your inbox? Sign up for Going(there’s a free version!) to get alerts when fares drop on your favorite routes. Going’s a membership-based service that finds huge discounts, mistake fares, and points-and-miles deals. Free accounts are great for domestic deals, while Going Premiumunlocks international winter getaways for up to 90% off.

Below are my top winter destinations in 2026 with cheap flights, great weather, and easy itineraries, from Caribbean beaches to fun city breaks.

Transparency Note: This post contains affiliate links. If you book through them, I may earn a small commission at no extra cost to you.