Pickledilly seeks 40 percent expansion, adding four pickleball courts in Skokie

Pickledilly’s courts were already full, and that pressure was enough to push Skokie toward a bigger footprint. The Skokie Village Board unanimously backed revisions Monday that would let the indoor pickleball club add four courts and roughly 15,000 square feet, an expansion of about 40 percent.

The request, filed by Pickledilly LLC at 4919 Main St. in Skokie, would allow the club to take over adjacent tenant space at 4913 Main St. The additional room could bring more restrooms, storage, seating and possibly a turf game area, giving the venue a broader mix of recreation and event space. Village officials said the existing off-street parking supply should still be enough, even with changes to circulation and ADA-accessible parking spaces.

That pace is notable because Pickledilly opened only in 2025 with 11 full-size courts and one half-size training court. The club’s own materials describe it as an 11.5-court indoor facility, and the space has already been used for learn-to-play classes, leagues, competitions and corporate events. Co-owner and managing partner Lauren Busey said the business has been thriving and that the courts are full, which is why the company is looking for more room.

Pickledilly first announced its plans in September 2024, when owners Lauren Busey, Amy Lillibridge, Nathan Cachila and Armi Cachila said the club would open in early 2025. Crain’s Chicago Business reported at the time that the renovated industrial building would sit near Sketchbook Brewing and the Skokie Valley Trail and include on-site parking, with tiered memberships and guest play available without a membership commitment. Earlier local reporting had already framed the project as an 11-court indoor facility, making the new request a fast follow to the original approval.

The timing gives Skokie a clear case study in how quickly a pickleball venue can move from promise to demand. With the board now supportive and a final approval step scheduled for the June 1 meeting, Pickledilly has gone from a new arrival on Main Street to a club testing the limits of its first buildout.