Chicago in September

Summer is peak Chicago — festivals every weekend, beach weather, and the city finally thaws out. But July and August bring crowds and hotel prices that'll make you wince. Late spring and early fall offer the sweet spot: pleasant weather without the summer madness. May through October gives you the full Chicago experience, from outdoor concerts in Millennium Park to Cubs games at Wrigley. Winter has its charms if you don't mind bundling up — the Christmas markets, cozy museum days, and surprisingly good theater scene. Plus hotel rates drop significantly. But here's the reality: January temperatures regularly hit single digits, and the wind off the lake makes it feel even colder. March and April can be unpredictable — you might get 70-degree days or surprise snowstorms. Pack layers no matter when you visit.