In 1975, Rodeo Riders was founded in Elkhart, Indiana under the original name Rodeo Riders, Inc., although the original club patch read Rodeo Riders Indiana. With several Leather/Levi Clubs surrounding Indiana, the Founder, Ernie Day, felt that it was about time a club was established in Indiana.

Rodeo Riders original membership of 8 was from Elkhart and Chicago, however, as the club grew, most of the members resided in Chicago. As a result, it became a Chicago based Leather/Levi Club. The highest membership was 18 and the lowest 2.

Meetings were held at the home of members on the 3rd Saturday of the month. Rodeo Riders officer titles were adopted with a Western flavor. They were Foreman (President), Ranger (Vice President), Top Hand (Secretary), Paymaster (Treasurer), and Trail Boss (Road Captain). Currently the office of VP is referred to as Sidekick. The official club colors are gold and black.

In June, 1975, Rodeo Riders accepted their first Associate Member, Peter Thomas. He later went on to become the first Foreman of the club.

Rodeo Riders' first home bar was the Snake Pit, a raunchy but great home bar. The first club night was held at the Snake Pit on April 24th, 1976. Other home bars were the Iron Butterfly, Redoubt, and Touché'. Touché' has been the Rodeo Riders' home bar for 20 plus years.

Rodeo Riders' first trophy was for 2nd Place Participation at Tribe, Detroit Do-A-Fool, April 1976. Introduced at this event was the official club cocktail, Red Eye. The current club cocktail is Sasparilla.

In August 1976, Rodeo Riders received their first club colors from the Selectmen of Detroit. At a special club night in September at the Interchange Bar-Detroit, hosted by Rodeo Riders, the club presented their colors for the first time to the Selectmen of Detroit.

On October 9, 1976, Rodeo Riders officially became a member of the Mid-America Conference of Clubs. The next day, October 10th, Rodeo Riders was incorporate in the State of Illinois.

On December 1, 1976, Rodeo Riders held their first anniversary, "Rodeo 1". It was a huge success attracting 205 participants, which at the time was the biggest club event in Chicago. The term, Rodeo, was introduced by Tony Llad, then a member for many years. Also at this anniversary, the Rodeo Riders' Constitution and By-Laws were formally signed by the Charter Members, Ernie Day, Sean Wagner, and Phil Taman.

On September 20, 1989, Rodeo Riders, Inc. officially became Rodeo Riders Chicago. A new club patch was introduced in 1990 by Peter Thomas. Rodeo Riders Chicago, like so many other clubs, suffered the loss of members to AIDS, however, even with these losses, Rodeo Riders Chicago was determined to carry on as a club.