Travel Advisor

Jacqueline Flaherty

She/Her

Expertise

San Diego,
France,
Luxury Travel,
Family Travel

Based in

Hinsdale, Illinois

Travel Advisor

Jacqueline Flaherty

Profile details

About

A Chicagoan who literally never says no to an opportunity to travel.

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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

View out a hotel window of green trees and white houses beside the sea

Trip Report

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...

An image of two colorful archways and outdoor seating. There are trees and a blue sky in the background.

Guide

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 ...

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Favorite hotels

Hotel Del Coronado

Experience timeless elegance and beachfront allure in San Diego, where historic charm, stunning ocean views and Southern California relaxation converge.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Hotel Lungarno

A riverside retreat in Florence offering timeless elegance, curated art, and stunning views of the Ponte Vecchio.

Fora Perks

★
$100 food / beverage credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Grand Hotel Mackinac Island

Step back in time and embrace timeless elegance at this historic gem overlooking the stunning waters of Lake Huron.

Auberge du Jeu de Paume, Chantilly, Relais & Chateaux

Experience French elegance and historic beauty, where luxury accommodations, gourmet dining, and the allure of Chantilly create an enchanting stay.

Fora Perks

★
$100 food / beverage credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Jacqueline's travel photos

Dinning area of a restaurant with beautiful views

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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

Jacqueline Flaherty curated by Jacqueline Flaherty

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).