Travel Advisor

Jacqueline Flaherty
She/Her
Expertise
- San Diego,
- France,
- Luxury Travel,
- Family Travel
Based in
Hinsdale, Illinois
Profile details
About
A Chicagoan who literally never says no to an opportunity to travel.
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.
Jacqueline's travel guides & trip reports

Site Inspection at The W Algarve in Albufeira, Portugal

Three Days in Mexico City
Favorite hotels
Jacqueline's travel photos




Jacqueline's reviews
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!!!
- Emily G.
Booked travel to Paris
- April 2025
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!
- Carrie M.
Booked travel to Chicago
- April 2025
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!
- Kevin M.
Booked travel to Orlando
- April 2025
Seamless booking and arrival!
- Alison K.
Booked travel to Florida
- April 2025

Get in touch with Jacqueline
Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can expect a response from Jacqueline within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).
