I think the flight looks pretty good, although weather is forecast all around that area, it's pretty devoid of weather at this post. FLL may have a bit of weather at landing time, but overall I think things look ok for SJO FLL. I'll write FLL to ORD later today.
Looks like light to moderate all the way up to MDW, stormy over Florida, ride looks better past northern Florida, more on the occasional and lighter side. Light to moderate on descent and landing in MDW.