Easiest way to tell is to get the brochures, and go check some out. Both are made by the same company of course and both are very good in their own way. Generally speaking both brands are the same structurally and the differences are in the cosmetics. The Itascas will have more decorative effects, like more mirrors, fancier lights, etc. We bought an Itasca because we liked the looks and more importantly the dealership ( it was smaller and more personal ) than the Winnebago dealer. The Itasca dealer was actually a little further away from us than the Winnie- by about 30 miles - but close enough to not sway our decision. I've heard that some things come standard on the Itasca that are optional on the Winnie, I never checked to find out and also was told the base price on the Itasca is slightly higher than the Winnie, again I never checked since when we got down to actually pricing out an RV we had already decided we wanted an Itasca, so we were pricing different Itasca dealers against each other and not different brands. The biggest deciding factor for us was the dealership.
Steve & Nancy
2005 Itasca Sunrise 33', W20 Chassis, Ultrapower, Henderson Trac Bar
2012 Chevy Captiva Sport AWD, ReadyBrute Elite Tow Bar, Blue Ox Base Plate, Protect-A-Tow