O’Leary’s Contractors Equipment and Supply, Inc. opened their doors 66 years ago in Chicago, Illinois and continue to have success to this very day. As a matter of fact, the family-owned business is not only having success; they are still growing each and every year.


O’Leary’s offers construction and industrial equipment, serving contractors with equipment rental, sales and service for industrial, municipal and utility companies. John J. O’Leary Sr. and his wife Ruth started the business back in 1949 in a one-room office on Lake Street in Chicago. 11 years later, John Sr. and Ruth moved their operation to West North Ave. and in 2010 they moved again to a six-acre site with over one thousand sq. ft. of indoor space.

Prior to opening O’Leary’s, John Sr. came from a construction equipment background, working as an operating engineer as well as a salesman in the Chicagoland area for Thor Construction Tool Co. While he worked at those jobs, he started to lay the groundwork for his future company.


The O’Leary rental business came as a result of his customers at Thor wanting and asking for additional products that complimented the Thor air tools, but John Sr. was limited on what Thor manufactured. He reached an agreement with the company to start his own rental and sales yard in 1949 with help from his wife Ruth that would offer additional products, like compressors to accompany the Thor air tools. In 1972, Ruth took over and ran the company until 1991 before she appointed her son John O’Leary Jr. president of the company, a position he holds to this day.

The company continues to grow by putting in the time to update and modernize their equipment on a regular basis. Customers appreciate the expanded list of products O’Leary’s offers and if they do not offer it, they will go out of their way to get it. They also prep and test all units before delivery to make sure they are properly working and only sell top named manufacturer’s equipment that offer 100 percent factory support.

“We always keep with the times by updating and modernizing our equipment and procedures,” said John O’Leary Jr. “Our customers are loyal because of the excellent service and care that we provide. If we are good to the customer and offer great service and products, everything takes care of itself. We are loyal to our customers and in turn, they have been very loyal to us.”

With support high on their list for manufacturer consideration, O’Leary’s came across the Chicago Pneumatic brand a few years ago and have been very happy since introducing CP products into their lineup. They added a few Chicago Pneumatic products at a time and now feature CP’s air tools, chipping hammers, rivet busters, paving breakers, rock drills and portable air compressors.

20150528_144354_resized-WEB“Chicago Pneumatic has an incredible sales and mechanical support team,” John O’Leary Jr. said. “Any products in our business need to be heavy duty because rental equipment can get pretty beat up. So, no matter what brand you have, you need to have a backup and support team in sales, service and so on. Chicago Pneumatic has that and we are very happy to offer their products in our lineup.”

The rental company most recently acquired the AR90G Small Articulated Tandem Ride-On Asphalt Roller that Chicago Pneumatic released in 2014. The AR90G is a gasoline version that is utilized primarily for small-scale compaction work such as patching, bicycle paths, small parking lots, and driveways. The roller features vibration on the front drum, with drive on both the front and rear drums. Chicago Pneumatic also offers the AR100 Small Articulated Tandem Asphalt Roller and the AR120 Compact Articulated Tandem Asphalt Roller.

“The AR90G is a well-built, sturdy piece of equipment that is heavy duty – which makes it a perfect fit for both owning and renting,” John O’Leary Jr. said. “The CP rollers have been popular with our small contractors and they have had a great amount of success on the jobsite with them. They have really complimented our compaction lineup and done a nice job for our customers.”

Like John O’Leary Jr. said, when you are progressive in your approach to business and treat the customers right, everything will take care of itself. That recipe has never changed since the O’Leary family opened their doors in 1949. Their mantra has not only kept them in business for 66 years, it has helped them climb to new heights.