Chicago

Chicago pickleball is a story of converting tennis. The city's parks (Horner, Margate, Lincoln, Welles) repainted dozens of tennis courts to handle the demand, and the suburbs (Naperville, Oak Park, Evanston) built dedicated complexes. The Big Ten Athletics-grade indoor complexes in the western suburbs run year-round leagues.

Winter shifts everything indoors. Chicken N Pickle Schaumburg, The Pickle Pad, and several converted-warehouse clubs in the suburbs handle the December-March crowd. Lakefront play (Diversey Driving Range, Diversey courts) starts up by April and runs through October. Public courts here are mostly unlit but the rec centers and ARC clubs have lights.

If you want a gritty, friendly, all-skill-levels game, Chicago has it. Bring a hat for sun and a fleece for the lake breeze.