Where to Jump (Chicago or Florida) - Memorial Day Weekend in Events & Places to Jump April 30, 2015 I would opt for Arizona over Chicago during Memorial Day. Having lived in Chicago for a decade...my home DZ was Skydive Chicago...love my roots, but it will rain. Let me be clear...it will rain all weekend. It rains every Memorial Day in Chicago, that is just the way it is. Ask anyone from the midwest if the weather is at all expected to be favorable for Memorial Day...they will tell you...it will rain. Expect to hear Tom Skilling on WGN Weather talk about the "cut off low pressure system" that is "parked over the Tri-State Region" bringing rain and heavy overcast for the entire Memorial day week. It will start raining on Weds before Memorial Day...and the rain will end the Weds after Memorial Day. Then it will be sunny on Thursday and Friday the week after the holiday, only to start raining again Saturday morning the following week...it will drive you to drink. I almost blew my head off living there... Now on the other hand...in Arizona...I can predict with 100% accuracy, that we will have bright sun and favorable conditions.