Travel Advisor

Jackie Singer

She/Her

Expertise

Boutique Travel,
Family Travel,
Europe,
LGBTQ+ Travel

Based in

Chicago's North Shore

Languages spoken

English, Spanish

Travel Advisor

Jackie Singer

Profile details

About

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 bespoke experiences. I love boutique hotels, off-the-beaten-path excursions and immersive cultural adventures. I can work within any budget to create your dream vacation!

Favorite hotels

The Hoxton, Amsterdam

Stylish hotel with quirky charm in a canal house on the Herengracht canal in central Amsterdam.

Fora Perks

★
Welcome amenity.
★
Upgrade & extended check-in/out whenever possible.

Downtown Los Angeles Proper Hotel

Sleek property in a building from the 1920s with upscale rooms and suites.

Fora Perks

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

Sui Posada Boutique Hotel

Sui Posada Boutique Hotel in Medellin is a charming and intimate accommodation nestled in the heart of the city's vibrant Laureles neighborhood.

The Click Clack Hotel Bogota

A unique and memorable stay that blends bold design with a stylish and modern stay in the heart of the capital.

Jackie's travel photos

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Jackie's reviews

Jackie is super helpful and easy to work with. I would highly recommend her!

Caroline K.
Booked travel to Madrid
March 2025

Jackie was great to work with. Her itinerary was perfect for our week in Barcelona. So glad we stayed a week so we could enjoy everything Jackie had planned including 2 day trips. We can’t wait to plan our next trip with Jackie.

Kara G.
Booked travel to Barcelona
March 2025

Jackie is amazing! Listened to all our needs - putting us in the right location for what we wanted to do and made all the arrangements for our tour to the Grand Canyon! It was the best time and so thankful for her guidance and knowledge!

Sarah M.
Booked travel to Scottsdale
January 2025

Jackie is an absolutely outstanding travel advisor! She is communicative, attentive, and works hard to find deals. As an extra perk, she somehow arranged for us to have treats in our room on arrival. Without question, I will always consult with Jackie when planning future trips. Jackie rocks!

Lisa D.
Booked travel to Mexico City
January 2025

Get in touch with Jackie

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Jackie within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).