Jacqueline Flaherty
She/Her
Based in Hinsdale, Illinois
English
Ask me about
My Story
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.
Stay connected
Reviews (28)
Kathryn C.
2 months ago
Jackie was an incredible help in planning our stay. We originally planned to drive in and out of the city each day for the Cubs Convention, but at the last minute decided to book a hotel. I reached out to Jackie, and she immediately sent several options within our price range, thoughtfully highlighting choices that would offer extra fun for our kids.
Our room included breakfast, a food and beverage credit, and access to a pool. We were also surprised with a welcome fruit plate, which the kids absolutely loved. Thanks to these special touches, the kids experienced room service for the first time (a huge hit!) and even enjoyed a Starbucks treat as we headed home.
Communication was clear and seamless—Jackie answered all of my questions quickly and helped make our weekend in Chicago truly amazing. We will absolutely be reaching out to Jackie and her team for future trips and will be recommending them to friends and family.
Lauren J.
2 months ago
We will continue to use Jacqueline for all of our future travel. Her attention to detail truly sets her apart.
Kelly M.
2 months ago
Jackie combines infectious energy and charisma with flawless attention to detail. She makes travel planning exciting while ensuring every detail is perfectly handled. You can relax knowing everything is in expert hands.
Jay M.
3 months ago
Always does a great job of communicating, really detailed with how the trip operates and has wonderful recommendations
Emily G.
a year ago
Jackie nailed our vacation in Paris with all the things we wanted to do for my mom's 70th birthday. She couldn't have been happier with the outcome of this trip. We stayed at the most beautiful and perfect hotels and had wonderful tours and an incredible show at the Saint Chapelle. Will work with Jackie again!!!
Kathryn C.
2 months ago
Jackie was an incredible help in planning our stay. We originally planned to drive in and out of the city each day for the Cubs Convention, but at the last minute decided to book a hotel. I reached out to Jackie, and she immediately sent several options within our price range, thoughtfully highlighting choices that would offer extra fun for our kids.
Our room included breakfast, a food and beverage credit, and access to a pool. We were also surprised with a welcome fruit plate, which the kids absolutely loved. Thanks to these special touches, the kids experienced room service for the first time (a huge hit!) and even enjoyed a Starbucks treat as we headed home.
Communication was clear and seamless—Jackie answered all of my questions quickly and helped make our weekend in Chicago truly amazing. We will absolutely be reaching out to Jackie and her team for future trips and will be recommending them to friends and family.
Lauren J.
2 months ago
We will continue to use Jacqueline for all of our future travel. Her attention to detail truly sets her apart.
Kelly M.
2 months ago
Jackie combines infectious energy and charisma with flawless attention to detail. She makes travel planning exciting while ensuring every detail is perfectly handled. You can relax knowing everything is in expert hands.
Jay M.
3 months ago
Always does a great job of communicating, really detailed with how the trip operates and has wonderful recommendations
Travel ideas (2)
Site Inspection at The W Algarve in Albufeira, Portugal
In March of 2024, I was able to tour the stunning W Hotel in the Algarve region of Portugal. Every detail was considered as this hotel was constructed and so tastefully designed. This property is versatile to welcome couples, friends and families. I am looking forward to returning to the W to experience everything it has to offer, from direct beach access to the expansive pool deck.
Site Inspection at The W Algarve in Albufeira, Portugal
In March of 2024, I was able to tour the stunning W Hotel in the Algarve region of Portugal. Every detail was considered as this hotel was constructed and so tastefully designed. This property is versatile to welcome couples, friends and families. I am looking forward to returning to the W to experience everything it has to offer, from direct beach access to the expansive pool deck.
Three Days in Mexico City
Mexico City holds a special place in my heart as a destination that truly embodies the essence of vibrant culture, rich history and delectable cuisine. The city's incredible food scene, bursting with flavors and textures, showcases the diverse culinary traditions that have shaped Mexico's gastronomic identity. Beyond its culinary delights, Mexico City's captivating history comes to life through its imposing landmarks, ancient ruins and impressive museums. The city's past is woven into its streets, offering a fascinating glimpse into the ancient civilizations that once thrived in the region. With its unparalleled mix of gastronomy, culture and history, Mexico City is a destination that never fails to inspire and delight. My curated travel guide aims to showcase the best of this dynamic city, allowing travelers to immerse themselves in its unique charm and uncover the hidden gems that make it a must-visit destination.
Three Days in Mexico City
Mexico City holds a special place in my heart as a destination that truly embodies the essence of vibrant culture, rich history and delectable cuisine. The city's incredible food scene, bursting with flavors and textures, showcases the diverse culinary traditions that have shaped Mexico's gastronomic identity. Beyond its culinary delights, Mexico City's captivating history comes to life through its imposing landmarks, ancient ruins and impressive museums. The city's past is woven into its streets, offering a fascinating glimpse into the ancient civilizations that once thrived in the region. With its unparalleled mix of gastronomy, culture and history, Mexico City is a destination that never fails to inspire and delight. My curated travel guide aims to showcase the best of this dynamic city, allowing travelers to immerse themselves in its unique charm and uncover the hidden gems that make it a must-visit destination.
Site Inspection at The W Algarve in Albufeira, Portugal
In March of 2024, I was able to tour the stunning W Hotel in the Algarve region of Portugal. Every detail was considered as this hotel was constructed and so tastefully designed. This property is versatile to welcome couples, friends and families. I am looking forward to returning to the W to experience everything it has to offer, from direct beach access to the expansive pool deck.
Site Inspection at The W Algarve in Albufeira, Portugal
In March of 2024, I was able to tour the stunning W Hotel in the Algarve region of Portugal. Every detail was considered as this hotel was constructed and so tastefully designed. This property is versatile to welcome couples, friends and families. I am looking forward to returning to the W to experience everything it has to offer, from direct beach access to the expansive pool deck.
Three Days in Mexico City
Mexico City holds a special place in my heart as a destination that truly embodies the essence of vibrant culture, rich history and delectable cuisine. The city's incredible food scene, bursting with flavors and textures, showcases the diverse culinary traditions that have shaped Mexico's gastronomic identity. Beyond its culinary delights, Mexico City's captivating history comes to life through its imposing landmarks, ancient ruins and impressive museums. The city's past is woven into its streets, offering a fascinating glimpse into the ancient civilizations that once thrived in the region. With its unparalleled mix of gastronomy, culture and history, Mexico City is a destination that never fails to inspire and delight. My curated travel guide aims to showcase the best of this dynamic city, allowing travelers to immerse themselves in its unique charm and uncover the hidden gems that make it a must-visit destination.
Three Days in Mexico City
Mexico City holds a special place in my heart as a destination that truly embodies the essence of vibrant culture, rich history and delectable cuisine. The city's incredible food scene, bursting with flavors and textures, showcases the diverse culinary traditions that have shaped Mexico's gastronomic identity. Beyond its culinary delights, Mexico City's captivating history comes to life through its imposing landmarks, ancient ruins and impressive museums. The city's past is woven into its streets, offering a fascinating glimpse into the ancient civilizations that once thrived in the region. With its unparalleled mix of gastronomy, culture and history, Mexico City is a destination that never fails to inspire and delight. My curated travel guide aims to showcase the best of this dynamic city, allowing travelers to immerse themselves in its unique charm and uncover the hidden gems that make it a must-visit destination.
Travel photos
