The Chestnut Hill Academy Squash Club is an athletic facility located at the end of West Willow Grove Avenue. The club is managed by squash coach Mike Jefferys, who prides himself on the club's upkeep, care and accessibility. The club is home to roughly 150 members of all ages and skill levels. Guests are welcome to try the facility up to three times before deciding whether or not to join. Members enjoy six full-sized courts, two of which are professional grade. The facility also features a changing room, as well as treadmills and bikes.  

The club has evolved over the years, but one thing is consistent: standouts who cut their teeth at Chestnut Hill often return to pay it forward to the next generation of students. The club was selected to host a professional tournament in October of 2010.