Jen Dine
Based in Chicago
Trips starting at $500/night
Jen Dine
Ask me about
My Story
As both a luxury travel advisor and a mother navigating the college years, I understand how meaningful travel can shape family memories and major life moments. I love helping clients plan everything from milestone vacations to college visit trips that feel inspiring, organized, and enjoyable.
Travel Style
My approach blends luxury with warmth and authenticity. I gravitate toward stylish hotels, memorable meals, charming neighborhoods, and experiences that help travelers feel connected to a destination rather than simply passing through it.
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Reviews (26)
Patrick H.
travel to Rome
12 days ago
Jen Dine is a treasure.
Elizabeth C.
travel to Paris
3 months ago
Jen is the best to book with and would recommend anyone to book with her!! She knows what she is doing as she is well traveled and has similar hotels standards!
Tiffany E.
travel to New York City
5 months ago
Working with Jen was absolutely top notch from start to finish. She secured the best available rate plus a breakfast package, which made the stay feel even more elevated and seamless. Every detail was handled thoughtfully. What really stood out was her follow-up at every step — before arrival, during the stay, and even when I needed to revise part of the trip. She managed adjustments quickly and effortlessly, taking all the stress out of the process.
James B.
travel to Fort Lauderdale
5 months ago
Jen was amazing, she booked this for us on the fly at the last minute when the Indiana Hoosiers made it into the National Championship. She coordinated our stay and helped up find the perfect spot!
Amy D.
travel to Playa del Carmen
6 months ago
Jen is hands-down our go-to travel agent. She always does an amazing job booking trips for us, pays close attention to every detail, and makes everything feel effortless. From securing hard-to-get dining reservations to lining up excursions perfectly, she gets it right every single time. We trust her completely and wouldn’t plan a trip without her. FIVE STARS!
Patrick H.
travel to Rome
12 days ago
Jen Dine is a treasure.
Elizabeth C.
travel to Paris
3 months ago
Jen is the best to book with and would recommend anyone to book with her!! She knows what she is doing as she is well traveled and has similar hotels standards!
Tiffany E.
travel to New York City
5 months ago
Working with Jen was absolutely top notch from start to finish. She secured the best available rate plus a breakfast package, which made the stay feel even more elevated and seamless. Every detail was handled thoughtfully. What really stood out was her follow-up at every step — before arrival, during the stay, and even when I needed to revise part of the trip. She managed adjustments quickly and effortlessly, taking all the stress out of the process.
James B.
travel to Fort Lauderdale
5 months ago
Jen was amazing, she booked this for us on the fly at the last minute when the Indiana Hoosiers made it into the National Championship. She coordinated our stay and helped up find the perfect spot!