Jacqueline Flaherty
Based in
Hinsdale, Illinois
Expertise
Family Travel, Luxury Travel, Couples Travel, Europe, Mexico, Japan
About
The Weekend Discovery is a Hinsdale, Illinois—based modern travel advisory focused on creating undeniably elevated, seamless travel experiences. We take our clients’ vision for their next trip and refine it through deep destination knowledge, strong global hotel partnerships, and thoughtful planning to deliver travel that feels intentional, well-paced, and beautifully handled.
Founded in 2023 by Jackie Flaherty, The Weekend Discovery grew out of a passion for smart logistics, great hotels, and meaningful travel moments. With a background rooted in relationship-driven work and hands-on travel experience, Jackie built the firm to serve travelers who value access, discretion, and a collaborative planning process. Today, The Weekend Discovery works closely with top hotels and trusted on-the-ground partners worldwide, helping clients travel with confidence—knowing every detail has been considered before they arrive.
Travel Style
Our clients care about great hotels, thoughtful details, and travel that feels elevated without being fussy. They do not want to spend weeks researching, second-guessing, or coordinating every moving part. They want it handled well.
We work with busy families who want to actually take the trip and do it right, and with couples who want meaningful time away together without the stress of planning it. In many cases, we step in as the lead planner, managing logistics and coordinating details so our clients can focus on the experience instead of the to-do list.
We care about the details that make a trip feel easy once you are in it. The right hotel, the right room category, smooth arrivals and departures, and a plan that leaves room for the moments you cannot schedule. It is a thoughtful structure with space for the unexpected.
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