Debra Winke
She/HerBased in Chicago
Debra Winke
Ask me about
My Story
Food, wine, and travel are my love language. Based in Chicago, I craft bespoke trips packed with personality, perks, and zero stress. Whether it’s a luxury getaway or a once-in-a-lifetime escape, I handle every detail so you can focus on making memories.
Travel Style
I’ve always loved travel because it lets you see the world through a different lens. I’m drawn to luxury experiences, but I also love uncovering hidden gems that make a trip truly unique. I believe every journey should include a few splurges on what matters most to you—it’s those touches that make it unforgettable.
I’m equally inspired by iconic destinations and underrated escapes, always on the hunt for the best hotels, the right perks, and incredible value. My goal is to create seamless, stress-free luxury travel that feels effortless yet extraordinary. From securing VIP perks to perfecting every detail, I do the work—you live the dream.
Reviews (18)
Sherif M.
travel to Paris
about 2 months ago
Great experience overall - Debra found us this hotel with the specific view we were looking for in Paris when a number of other hotels were already sold out.
Arleen D.
travel to San Antonio
3 months ago
First time working with FORA program/Luxury Advisor. Deb was outstanding! She walked me through benefits, booked reservation, responsive in follow-ups, hand-written note on arrival was very nice touch and thoughtfully listened when I had to contact her to share experience related to stay and offered to assist. Resolving issue related to X2 Hilton points. While waiting to depart hotel connected with another guest having issues with their Hilton reservation. I provided Deb’s contact information as referral as our experience had been wonderful with Deb!
Klaire K.
travel to Banff
6 months ago
Debra was absolutely wonderful to work with. Communication was always timely, clear, and incredibly helpful throughout the entire planning process. She truly listened to our preferences and made thoughtful recommendations that elevated our trip and took the stress out of planning.
Corey J.
travel to Switzerland
8 months ago
Debra is a pro, period. Her personal experiences at so many of the places she works with are a massive plus. Delightful and we will use Debra's expertise every time we travel in the future! Highly recommend!!
Dawn H.
travel to Palm Beach
9 months ago
This was our first experience with booking travel thru Debra & I can say this will be our only option moving forward. Debra made the planning process fun rather than clumsy & daunting…her expert opinions were priceless. Champagne region was beyond memorable & I thank Debra for making the experience perfect.
Sherif M.
travel to Paris
about 2 months ago
Great experience overall - Debra found us this hotel with the specific view we were looking for in Paris when a number of other hotels were already sold out.
Arleen D.
travel to San Antonio
3 months ago
First time working with FORA program/Luxury Advisor. Deb was outstanding! She walked me through benefits, booked reservation, responsive in follow-ups, hand-written note on arrival was very nice touch and thoughtfully listened when I had to contact her to share experience related to stay and offered to assist. Resolving issue related to X2 Hilton points. While waiting to depart hotel connected with another guest having issues with their Hilton reservation. I provided Deb’s contact information as referral as our experience had been wonderful with Deb!
Klaire K.
travel to Banff
6 months ago
Debra was absolutely wonderful to work with. Communication was always timely, clear, and incredibly helpful throughout the entire planning process. She truly listened to our preferences and made thoughtful recommendations that elevated our trip and took the stress out of planning.
Corey J.
travel to Switzerland
8 months ago
Debra is a pro, period. Her personal experiences at so many of the places she works with are a massive plus. Delightful and we will use Debra's expertise every time we travel in the future! Highly recommend!!
Travel photos

