Step 1: We need to find the probability that two randomly selected squares on a chessboard share a side. A standard chessboard has \(8 \times 8 = 64\) squares.
Step 2: The total number of square pairs is \(\binom{64}{2}\).
Step 3: We determine favorable outcomes by counting adjacent square pairs. Each square has up to 4 neighbors. The total count of adjacent square pairs is less than 64, considering only squares that share a side.
Step 4: Calculating the ratio of adjacent pairs to total pairs yields the probability \(\frac{1}{18}\).