Jackie Singer
She/HerBased in Chicago's North Shore
English, Spanish
Jackie Singer
Ask me about
My Story
A therapist-turned-travel advisor who brings her passion for connection and experience to her love of travel.
Travel Style
I am passionate about prioritizing the needs of each of my clients and creating truly bespoke travel. I love boutique hotels, off-the-beaten-path excursions, and immersive cultural adventures. When I am traveling, you can find me exploring the hidden gems of a city, day-tripping to those tiny towns, or in whatever body of water is nearby!
Reviews (19)
Juliet B.
travel to London
about 2 months ago
Jackie is phenomenal! She made planning this trip so easy and fun. She is smart, organized, and well-resourced. Her recommendations were spot on and I can't wait to book another trip with her!
Michelle M.
travel to Tokyo
5 months ago
Working with Jackie was a breeze. She is responsive, has great suggestions, and took all of the worry and chaos out of planning. Her itinerary page is amazing. Very easy to use and incredibly helpful. She thinks of all the details, which allowed us to have a wonderful, memorable experience.
Susan P.
travel to Cancún
8 months ago
Jackie went over and above to navigate through all the computer glitches. She was a pleasure to work with, and I hope to book another trip in the near future.
Juliet B.
travel to China
10 months ago
Jackie was spectacular in planning a three week trip to China and Japan. She is highly organized, provided excellent recommendations for hotels, activities, and good, provided a super user friendly itinerary that included detailed instructions on where to go, and provided support throughout the trip as things shifted. Jackie made the daunting task of planning a lengthy trip to Asia super easy and working with her made the planning process really fun. Her recommendations were invaluable and each one proved to be 100% on target. I look forward to booking my next trip with her! Much gratitude.
Kathleen H.
travel to Dublin
about 1 year ago
Jackie asked all the right questions while planning this trip. She made suggestions we had not thought of. When we needed to make significant changes due to extra travelers, she handled everything right away. Even when something didn’t go as planned, we were able to reach her immediately and she found a solution before we woke up the next morning. Her ability to plan activities and accommodations for our group was second to none. We had the trip of a lifetime to Ireland all due to her meticulous planning. We can’t wait for our next adventure planned by Jackie!
Juliet B.
travel to London
about 2 months ago
Jackie is phenomenal! She made planning this trip so easy and fun. She is smart, organized, and well-resourced. Her recommendations were spot on and I can't wait to book another trip with her!
Michelle M.
travel to Tokyo
5 months ago
Working with Jackie was a breeze. She is responsive, has great suggestions, and took all of the worry and chaos out of planning. Her itinerary page is amazing. Very easy to use and incredibly helpful. She thinks of all the details, which allowed us to have a wonderful, memorable experience.
Susan P.
travel to Cancún
8 months ago
Jackie went over and above to navigate through all the computer glitches. She was a pleasure to work with, and I hope to book another trip in the near future.
Juliet B.
travel to China
10 months ago
Jackie was spectacular in planning a three week trip to China and Japan. She is highly organized, provided excellent recommendations for hotels, activities, and good, provided a super user friendly itinerary that included detailed instructions on where to go, and provided support throughout the trip as things shifted. Jackie made the daunting task of planning a lengthy trip to Asia super easy and working with her made the planning process really fun. Her recommendations were invaluable and each one proved to be 100% on target. I look forward to booking my next trip with her! Much gratitude.
Travel photos





