David Wolff: How did Wolff's Flea Market Begin?

Don and I are often asked this question: How did Wolff’s Flea Market begin?   Over the years I have heard different versions of the answer from many people, but they are usually wrong.  Following is the official answer. 

Believe it or not, it all started in the early 1960’s!!  Our parents, Lawrence and Katherine Wolff were diehard flea market fans.  As kids, Don and I, along with our sister Eileen (who most of you know as our most loyal employee and ambassador) and brother Jeff (who can be found shopping at our market almost every Sunday morning) would be willingly dragged along on their weekly sojourn to one of the area’s local flea markets.  Back then there were many quality flea markets to choose from; Harlem & Irving (Chicago), 79th & Harlem (Bridgeview), Twin Drive In (Wheeling), and 7 Mile Fair (Southern Wisconsin).  We went to all of them and there were few Sundays in which we did not visit a flea market.  Even on vacation our family would take an excursion to the local market.  We had a tradition of stopping for lunch after leaving a flea market and bringing our purchases into the restaurant to share our finds with each other.  Flea markets were in our blood from an early age!

Fast forward to the early 1980’s.  Don and I still had the flea market bug.  We both continued to be regular flea market customers, but now also started selling various items at many of the local markets.  This would turn out to be helpful in our future endeavor as it gave us experience on both the customer and vendor side of the business.  Another important part of our evolution into the flea market business happened in 1980.  Don, Eileen and I started working at the Rosemont Horizon (later to become the Allstate Arena) vending T-shirts, programs and other novelties.  We started working there on the very first day of operation (Fleetwood Mac and Christopher Cross concert).  Don and I actually worked in the building during the final phases of construction.  Our dad had the contract to paint the aisle and row markers.  He recruited us to assist in this job.  Eileen still vends concession merchandise, making her one of the few employees working at the Allstate Arena/Rosemont Horizon from day one!!

Now we will take a trip to the late winter of 1990.  Don and I were working an event at Rosemont Horizon and took a break in the parking lot. The conversation turned into a discussion about what a great flea market this would make.  It had everything necessary; huge parking lot, accessible location and great visibility from the tollway.  We knew that what would be our largest competitor (Twin Drive In, Wheeling), would eventually be closing due to expansion of the Palwaukee Airport.  Don and I decided to take the next step and approach the Rosemont Horizon management and see if they had interest in leasing the lot to us.  To our surprise they said yes!  The fact that we had worked in the building for the past 10 years helped give management comfort in our ability and integrity. 

So, with much help from our parents, we opened for our first Wolff’s Flea Market in May of 1991.  I remember spending the night before opening day in my dad’s garage doing some final work on some of our booths and signs.  It was pouring rain.  I was thinking that all of our advertising was going to be wasted.  We probably would not even be able to open.  After a very short, restless night of sleep, I woke up to clear skies; PHEW!!!!   While that first day seemed small when compared to today’s standards, we were happy with the 125 vendors and 1500 customers who gave us a try!   Most of the vendors seemed to be happy, and many of them remain with us today.  Little did we know that we would still be operating 19 years later.

Stay tuned, I will write more about our evolution in future newsletters.


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