Chicago is 230+ sq miles, its a huge city. Parking on, say, far south side or NW side is very different than parking in hot neighborhoods or downtown. Unless you're paying for a space you're going to have issues with street parking in many areas.

A 210-250" car will absolutely present challenges street parking in many neighborhoods. My 170" car does sometimes due to average street space size. I can't imagine adding another few feet to my car and being happy with street parking experiences.