Jacqueline Flaherty
She/Her
Based in Hinsdale, Illinois
Jacqueline Flaherty
Ask me about
My Story
A Chicagoan who literally never says no to an opportunity to travel.
My Travel Style
My travel style encompasses using travel as a means to connect with people and reminisce about past adventures, all while seeking out thoughtful hotels and exceptional service that provide me with comfort and support along the way. I have a deep appreciation for immersing myself in new cultures and experiencing novel activities that broaden my horizons. Additionally, I dedicate myself to researching relentlessly before every trip so that my clients can rest assured knowing that their travel plans are meticulously curated and taken care of.
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My reviews (24)
Emily G.
8 months 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!!!
Carrie M.
8 months ago
Jackie Flaherty made our St. Regis Chicago stay absolutely unforgettable. From start to finish, she curated the perfect 40th birthday itinerary with incredible attention to detail. Every reservation, activity, and special touch was flawlessly planned—seamless spa appointments, fantastic dining experiences, and thoughtful surprises throughout. Her warmth, professionalism, and genuine care made us feel truly celebrated. Thanks to Jackie, our weekend was stress-free and filled with unforgettable moments. She’s a true gem!
Kevin M.
8 months ago
Jackie was super helpful with booking our stay. She checked in on us several times before our trip began with helpful travel reminders and good restaurants to check out on the property.
She was even helpful while there with our confirmation number that was lost in my inbox :).
Will definitely be staying again and having Jackie help us book!
Alison K.
8 months ago
Seamless booking and arrival!
Robin F.
9 months ago
We just wrapped up the perfect staycation in Chicago, and once again, Jackie at The Weekend Discovery made it unforgettable. From start to finish, her service was top-tier—she thought of every detail, from incredible welcome amenities for the kids (they were SO excited!) to a surprise for us that truly made the trip feel extra special.
We love the location she picked, and it’s always such a treat to enjoy the city we call home with a fresh perspective. Staycations through Jackie are anything but ordinary—she makes even a night or two away feel like a full-blown vacation. Highly recommend booking your next Chicago escape with her!
Emily G.
8 months 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!!!
Carrie M.
8 months ago
Jackie Flaherty made our St. Regis Chicago stay absolutely unforgettable. From start to finish, she curated the perfect 40th birthday itinerary with incredible attention to detail. Every reservation, activity, and special touch was flawlessly planned—seamless spa appointments, fantastic dining experiences, and thoughtful surprises throughout. Her warmth, professionalism, and genuine care made us feel truly celebrated. Thanks to Jackie, our weekend was stress-free and filled with unforgettable moments. She’s a true gem!
Kevin M.
8 months ago
Jackie was super helpful with booking our stay. She checked in on us several times before our trip began with helpful travel reminders and good restaurants to check out on the property.
She was even helpful while there with our confirmation number that was lost in my inbox :).
Will definitely be staying again and having Jackie help us book!
Alison K.
8 months ago
Seamless booking and arrival!
My 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.
My travel photos
