The best times to visit Chicago are from April to May and between September and October, when temperatures are warm, festivals are held, and crowds are manageable. The perfect time to visit Chicago is between April and June or between September and early November. You might prefer to visit the Windy City during other times of the year, but these are the times that attract people the most depending on the optimal weather, the crowds, and the things to do. The best time to visit Chicago is in late spring, in April and May, and in the fall months of September and October.
The temperatures during spring and autumn are pleasant and mild, and there is less rain and fewer tourists. May, June, September and October are the best months to visit Chicago if the weather is nice. These are the months that are warm enough to do outdoor activities without overheating. You'll also find a lot of events happening during these months.
While I think Chicago is a great place to visit all year round, most people would like to visit Chicago in the fall. If you're visiting between mid-March and early April, your visit may coincide with Chicago Restaurant Week, a two-week event where you can enjoy multi-course meals at fixed prices at some of the best places to eat in Chicago.