
Jessica Raciborska
She/HerBased in Chicago, Illinois
English, Polish
Trip budgets start at $300/night
Ask me about
My Story
Travel Geek Jess grew out of a lifelong love for travel. I always have my nose in a travel book learning about the best cities to visit, unforgettable national park hikes, noteworthy resorts, and local gems that make a place feel special. I bring my passion, curiosity, and insider knowledge to be your trusted travel advisor for unforgettable trips!
Travel Style
I bring a deep passion for thoughtfully curated travel for couples, from wedding weekend room blocks and honeymoons to milestone anniversaries and effortless resort escapes.
I support couples in destinations around the world, with current popular destinations being Portugal, Italy, and France for longer escapes, as well as the US, Caribbean, and Canada for quick getaways.
No matter the destination, my goal is to create an unforgettable trip tailored to your needs, so you can relax, celebrate, and fully enjoy every moment of your trip!
Reviews (15)
Georgia W.
6 days ago
Jess was fabulous to work with. She made everything so easy! She picked out a fabulous stateroom for our cruise that was close to the activities and elevators. She booked all the activities and even when one we wanted was fully booked she kept monitoring for cancellations and was able to snag us a coveted appt just days before the cruise! I really appreciated that. I liked the itinerary that she sent a few days before that summarized everything for us.
Camille V.
about 1 month ago
Jessica did a great job communicating with us during planning/booking and pre-travel before our trip to Cancun. She also helped us book our private transportation to/ from the airport and the hotel - which was nice not to worry about. Jessica provided us with an organized travel itinerary before our trip which I was able to print out and reference during our trip. Jessica was available for any and all questions we had pre-travel and even checked in with us during our trip to make sure everything was going smoothly. Thank you, Jessica!
Natalie M.
about 2 months ago
Jessica was an absolute pleasure to work with! She was so helpful in the booking process and responsive to all questions we had. She came with a ton of information and ensured we were ready to go for our trip. We’re so pleased with the service we received and will definitely be booking with her again!
Kendra K.
4 months ago
Jess is absolutely wonderful to work with! Even though our group size changed and our plans shifted, she remained incredibly helpful and supportive throughout the process. She put together fantastic recommendations for our Montana trip that we ended up using, and she even went above and beyond by securing us a resort credit after we’d already booked. Jess has planned other vacations for me in the past, and she’s always been thoughtful, knowledgeable, and genuinely invested in making sure we have the best experience possible. She’s simply the best!
Camille V.
5 months ago
Jessica did a great job planning our girls weekend getaway trip to Santa Fe! She provided a detailed itinerary in advance with plenty of additional activities and restaurant options and was open to any changes we wanted to make. Our trip was focused on relaxation, rejuvenation, and some light exploration. The hotel and day spa Jessica recommended were perfect for our trip. The hotel was centrally located which made it easy to walk around the downtown area. She was also able to get us complimentary breakfast and a resort credit by booking with her, which was much appreciated. Can’t wait to work with Jessica again on my next trip!
Georgia W.
6 days ago
Jess was fabulous to work with. She made everything so easy! She picked out a fabulous stateroom for our cruise that was close to the activities and elevators. She booked all the activities and even when one we wanted was fully booked she kept monitoring for cancellations and was able to snag us a coveted appt just days before the cruise! I really appreciated that. I liked the itinerary that she sent a few days before that summarized everything for us.
Camille V.
about 1 month ago
Jessica did a great job communicating with us during planning/booking and pre-travel before our trip to Cancun. She also helped us book our private transportation to/ from the airport and the hotel - which was nice not to worry about. Jessica provided us with an organized travel itinerary before our trip which I was able to print out and reference during our trip. Jessica was available for any and all questions we had pre-travel and even checked in with us during our trip to make sure everything was going smoothly. Thank you, Jessica!
Natalie M.
about 2 months ago
Jessica was an absolute pleasure to work with! She was so helpful in the booking process and responsive to all questions we had. She came with a ton of information and ensured we were ready to go for our trip. We’re so pleased with the service we received and will definitely be booking with her again!
Kendra K.
4 months ago
Jess is absolutely wonderful to work with! Even though our group size changed and our plans shifted, she remained incredibly helpful and supportive throughout the process. She put together fantastic recommendations for our Montana trip that we ended up using, and she even went above and beyond by securing us a resort credit after we’d already booked. Jess has planned other vacations for me in the past, and she’s always been thoughtful, knowledgeable, and genuinely invested in making sure we have the best experience possible. She’s simply the best!
Travel photos





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