
Tamara Jain
She/HerBased in Chicago, Illinois, USA
Tamara Jain
Ask me about
My Story
Applying two decades of planning travel for my family along with years of transactional law to build well-planned travel experiences.
My Travel Style
I love to travel and I love to maximize my clients’ travel experiences through well-planned travel itineraries balancing budget-savvy tricks and splurges. I strive to understand what is most important to my clients to help them find the right balance for their vacation.
My reviews (10)
Neil J.
15 days ago
Once again, Tamara was able to pull together an outstanding trip to Costa Rica on very short notice. It was a great combination of outdoor adventure, nature, local food, and some beach relaxation. Looking forward to engaging with her on more trips in the future!
Neil J.
a month ago
Tamara was instrumental in planning a weekend getaway to Denver. She managed the bookings for everyone in our party and made the entire process very easy. Well-Planned Travel will continue to be my "go to" whenever I'm planning any vacation.
Donna D.
2 months ago
Tamara was immensely helpful. She stayed on top of my reservation and was able to upgrade me without additional cost. I’m used to handling reservations on my own and Tamara put more thought and concern into my reservation than I have ever done. It was under her care that made the trip that much extra.
Mary K.
3 months ago
Great communication, incorporation of my wishlist items, and recommendations!!
Megan O.
4 months ago
Tamara was integral in making this first cruise for my husband and me happen. While trying to plan our trip ourselves, we almost gave up. When we reached out to Tamara, she was able to recognize our differing wants and needs and came up with a great plan that we both really enjoyed. She was extremely attentive not only while planning the cruise but also with planning excursions and giving us all the tips we needed for a good cruising experience. She stayed in contact throughout the planning process but didn’t overwhelm us. She was very knowledgeable and any answers she didn’t have, she researched immediately and got back to us with an answer. The goody bag she gifted us right before our departure was full of items that helped make our trip run smoothly. Working with Tamara was a great experience from start to finish.
Neil J.
15 days ago
Once again, Tamara was able to pull together an outstanding trip to Costa Rica on very short notice. It was a great combination of outdoor adventure, nature, local food, and some beach relaxation. Looking forward to engaging with her on more trips in the future!
Neil J.
a month ago
Tamara was instrumental in planning a weekend getaway to Denver. She managed the bookings for everyone in our party and made the entire process very easy. Well-Planned Travel will continue to be my "go to" whenever I'm planning any vacation.
Donna D.
2 months ago
Tamara was immensely helpful. She stayed on top of my reservation and was able to upgrade me without additional cost. I’m used to handling reservations on my own and Tamara put more thought and concern into my reservation than I have ever done. It was under her care that made the trip that much extra.
Mary K.
3 months ago
Great communication, incorporation of my wishlist items, and recommendations!!
My travel photos


