When is the best time to visit Chicago?

The best time to visit Chicago is during the Summer months - also known as "Summertime Chi." There are activities and events to check out including: art shows, running and aquatic events, and several outdoor music festivals.  Chicago offers a robust shopping and dining scene as well. It's popular to visit in the Summer based on weather conditions; the "Windy City" can be uncomfortably cold during the Winter months.