Jillian Urban

Owner, Travel Specialist

Racine, WI and Kissimmee, FL


I'm Jillian, and my husband Peter and I own Looking Glass Travel, LLC!

Welcome to our little travel agency!

As a single mother of 2 boys, I never really had a lot of money to take my kids a lot of places. We didn't have a lot of help, so I truly was 'doing it on my own', and we really had to budget our money. As a kid, our big family vacations were always 'up north' to my grandparents house in Necedah, WI, and sometimes to the Dells, and we'd never been to a major destination like Walt Disney World or anything like that. I grew up on a farm, with 2 working parents who never got vacations, so things like that were out of our reach.

I was determined to make sure that my kids would see more than just what our Southeastern Wisconsin life had to offer (not that SEWI is bad, there's TONS of stuff to do! But, there's more to life than the place that you live in)

In 2006, at the age of 29, I finally saved all the money I possibly could, lived on mac n' cheese and Pasta-roni for almost a year, and flew my sons, my mom and myself out to LA for the first time to spend a week at my cousin's house and go to Disneyland for the first time ever. We got discounted tickets from my cousin, I planned the whole trip myself, and the first stop we made was the Hollywood Walk of Fame. It was AMAZING! Glamorous, Stars on the cement in the ground, homeless people, knockoff characters walking around, the Hollywood sign on the mountains in the distance, cars zooming past on Hollywood Blvd, and I was in LOVE. We got hotdogs at Pink's, drove past the Whiskey a-go-go, and the very next day, set off for Disneyland! I couldn't believe it. I was in heaven.

To walk through the gates of Disneyland for the first time, you would have thought I was a child again. I'm not ashamed to say I cried, just to be there, walking down Main Street, smelling the popcorn and churros, seeing the castle for the first time, the blossoms on the trees behind the Partners Statue, and seeing Walt's Apartment above the Fire Station. It was a dream come true for me. My kids had a blast, and we rode every ride we possibly could, and stayed until the park closed each day we were there. Disneyland will always be my first love, my original 'home'.

From that moment on, I knew that I had to keep traveling with them. I knew that I had to make sure that we saw as much as we possibly could before they graduated and moved on with their lives. I knew that I didn't want them to know so little of the world like I did as a kid. As lovely as living in Wisconsin is, there's too much of the world to see!

In 2010, the day after Thanksgiving, Peter and I had our first 'non-date'. We had known each other for many years as friends, but never dated. Our lives had run parallel up until 2010, and we'd never considered each other more than just friends. The stars finally aligned and we went out to a show with some friends, and the rest is history! We got married in 2012, and our little Charlie graced us with his presence later that year.

Pete was never much of a traveler, so when I started taking him along for the ride, he was hesitant at first. But, boy, did that travel bug bite him hard! As my travel career blossomed, and he traveled with me, we decided that we wanted to make this our adventure together.

In 2015, Looking Glass Travel was born. Mostly out of necessity, because I did not want to give up my travel agency dreams. What's the saying? When one door closes, a window opens? Something like that. Anyways, One agency door closed for me, so I opened a window, a Looking Glass window. We started our own agency with the idea that maybe we would last a year, maybe 2, and be done. That wasn't the case, and we flourished!

Many years, and many wonderful specialists later, and we're thriving! We even survived a pandemic! It's been such an amazing ride, and we're having so much fun, living our dreams, and helping others live theirs as well. We literally make MAGIC for people, each and every day.


Facebook: facebook.com/lookingglasstravel

Instagram: instagram.com/looking_glass_travel

Tiktok: @lookingglasstravel

Email: jillian@lookingglasstravel.com