Chin turned professional when he signed with Orlando City of the USL Professional Division in 2011. He made his professional debut on 14 May 2011, coming on as a second-half substitute in a 1–0 win over the Pittsburgh Riverhounds. He then scored a goal and provided two assists in their first round match in the 2011 Lamar Hunt US Open Cup, in a 4–0 win over ASC New Stars. After spending the early portion of the 2011 season learning Orlando City Head Coach Adrian Heath's system, Chin came alive in the later part of the campaign and became known as the super-sub. As a result, the speedster ended his rookie season with four goals, two of which came during the Lions' memorable three-game playoff run, which saw the club secure its first USL PRO Championship. In December 2011, Orlando signed Chin to a contract extension through the 2014 season. Moving into his second season, Chin's confident play towards the end of his rookie year certainly carried over into his second term with the club. Dennis transitioned from his super-sub role, held in year one, to become the primary goal-scorer for the Lions. Chin's first goal came just three minutes into their first game of the season against the Charlotte Eagles, and would set the tone for the kind of year he was about to embark on. All season long, Chin's pace and finishing ability caused problems for opposing teams' back lines and led to the striker scoring 11 goals during league play, which was a team record. Those 11 goals were also good for best in the league and saw Chin finish as Top Goal Scorer and Scoring Champion of the USL Pro in only his second season as a professional. In addition, Chin also notched three assists during league play and also scored in the Lamar Hunt US Open Cup against Major League Soccer club Sporting Kansas City. Chin's impressive play led to the Oviedo native being named to the USL Pro All-League first team, while also being nominated for USL Pro Most Valuable Player and Central Florida Athlete of the Year. Dennis also accepted invitations to train with MLS sides Chicago Fire and D.C. United during the 2012 off-season. In his third year with Orlando City, Chin was once again an integral part of the Lions' Championship run. After notching five goals and five assists in the regular season, Chin was lethal in the playoffs and recorded four goals and three assists, in three games played, leading the USL Pro playoffs in both categories. Two of those four goals were scored in the USL Pro Championship match and helped Orlando City secure its second USL Pro title, after being upset by the Wilmington Hammerheads in the year prior. He was released upon the conclusion of the 2014 season, a casualty of the club's transition to Major League Soccer.
After exploring some opportunities in Europe, Chin ultimately signed with another USL team, Arizona United SC. He ended up scoring in the first two matches of 2015.
Ottawa Fury
In December 2015, Chin signed with Canadian NASL club Ottawa Fury FC. He scored one goal for Ottawa in 17 appearances in all competitions, including seven starts.
