The hot Chicago summer is the peak of the festival season, with major events taking place in the parks and neighbourhoods every weekend. September is blessed with reliably warm days and is probably the most pleasant month of the year, weather wise, but there's less going on during this period.
January to March is when Chicago is least busy and hotels and airfares are usually at their cheapest; however, temperatures and brisk winds will guarantee that you'll spend most of the time indoors.
They don't call it the 'Windy City' for nothin'. There's everything from cool, God-sent lake breezes at the height of summer to skirt-raising gusts in the spring to spine-chilling, nose-chiselling blasts of icy air in the winter. Late spring and early autumn are pleasant, being generally warm, clear and dry. July and August can get really hot, with temperatures from 27-32°C (80-90°F) and high humidity. Winters can be damp and cold - between -11°C and -2°C (12°F and 29°F) if you're lucky - and snowy for days on end.
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