Here's my rule that always helps with narrowing down options: Put convenience first. Prioritize the booking that will save you the most time and fit seamlessly into your travel plans. Book a direct flight if possible. Book the flight with the fewest stops if direct flights aren't available.

When planning a trip, the general rule of thumb is to book your flights first. This is because flight prices are far more volatile than hotel rates; a difference of a single day or even a few hours in your departure can change the cost of a ticket by hundreds of dollars. Once your transportation is locked in, you have the exact "anchor dates" needed to fill in the gaps with accommodations. However, there are two major exceptions to this rule. First, if you are traveling for a high-demand event—like the Olympics, a major music festival, or a solar eclipse—hotels will sell out or skyrocket in price long before flights do. Second, if you have your heart set on a specific, unique property with limited inventory (such as a national park lodge or a boutique riad), you should secure that reservation first. In 2026, most travelers use a "hybrid" approach: they research flight windows while holding "free cancellation" hotel rooms to ensure they have a place to stay while waiting for the best airfare deal.