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Lori Weiss

She/Her
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  • Based in icon

    Based in Chicago

  • Languages spoken icon

    English

  • Minimum booking icon

    Trips starting at $300/night

Ask us about

Cruises
Outdoors & Nature
Luxury Travel
Southeast Asia
Central America
Europe

Our Story

I’m a retired pediatrician who finds joy in planning meaningful journeys that connect people to culture, history, and nature. Travel fills my soul—and I’m always planning my next adventure.

Travel Style

I’m drawn to journeys that blend cultural immersion with meaningful experiences—whether that’s wandering through historic neighborhoods, savoring local cuisine, or spending time outdoors in nature. My most memorable trips have included learning about a destination’s people, history and architecture while also making space for scenic hikes, vibrant markets and quiet moments of reflection. I believe travel should be enriching, enjoyable, and worry-free—not stressful—so I focus on handling every detail with care, allowing my clients to be fully engaged in their experience.

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Reviews (16)

15 days ago

I don't ever give 5 stars but will for Lori! She is organized and on the ball despite having to herd cats (us). Helped us organize perfect multigenerational trip that worked for everyone.

17 days ago

Lori helped me create a trip to Spain that allowed me and my family to truly enjoy our time together without needing to stress over our schedule. We needed to tour three large cities in 7 days and we all walked away feeling like we got a good taste of each. Every restaurant, hotel, train trip and tour were prebooked and available on my phone app due to the planning Lori did with me. My young adult children and husband were so appreciative of the interactive experiences we provided them which meant so much to me. Highly recommend Lori as a travel agent!

4 months ago

Lori was a terrific advisor! Her communication was clear, timely, and responsive. It was evident that she cared about every member of our party and worked hard to attend to our many diverse needs. She found us an excellent vacation for an affordable rate, and I'm confident that our experience was tremendously improved through her advice and arrangements. Thanks, Lori!

4 months ago

Every day and night on this elegant ship were beautiful. Every guest from the ages of 1-76 years old had an awesome experience. All of this worked so well because our travel agent, Lori Weiss, was extraordinarily helpful. She put together a vacation that all age groups could enjoy. She made sure my handicapped needs were met at every situation. She arranged our meal times and room placements perfectly! Our group had vegetarian, pescatarian and carnivore food preferences and ALL of them had great meals accordingly. All of these factors were carefully considered for my family. Lori provided us all information from passports to medical advice- she met with all three families on Zoom calls as well as through e-mails and phone calls. She was always available for questions. We are so thrilled with our travel agent for making the Royal Caribbean a truly magnificent and magical experience for all ten of us! We have recommended both Lori Weiss and the Royal Caribbean to friends, and several of them are very interested in taking a similar trip. In summation, Lori Weiss and Royal Caribbean made our dreams come true.

M

Margaret R.

4 months ago

Lori was amazing. Helping us find a hotel where we could take advantage of an IHG deal, calling the hotel to ask our questions, and following up before our arrival to be sure all was in order.

Travel ideas (4)

Travel photos

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