Spring is one of the best times to visit Chicago. In May you’ll fine fewer crowds than during June, July and August, and flight and hotel prices are often lower. You’ll wait in shorter lines for major attractions like the Willis Tower but you’ll still find plenty to see and do. Plus, the weather is a pleasant middle crowds between frosty and sweltering – often warm and sunny during the day with a slight chill in the evening.
Temperatures range from 51-70°F with a few hot, summer-like days mixed in with cooler, windier, wetter days that recall early spring. You’ll need to pack for every contingency May (layers are key) and don’t forget to bring both an umbrella and some sunglasses.