Dallas Fort Worth Metroplex
Napa: Napa/Sonoma in one day
Don't do both, much too large and wine country - like good wine - should be savored! Try Scribe Winery, smaller and very friendly, in Sonoma, or Spring Mountain Vineyard in Napa - don't be scared by the $50 if you enjoy wine...
Chicago: Teen Trip to Chicago
Check out Wicker Park and Bucktown areas for good shopping, especially Wicker Park. Lincoln Park (Illinois) has some good stuff too on Armitage.
Chicago: Cheap but awesome places to go and see in the Chicago area
Wrigleyville, right near Wrigley Field is a great place to hang out. Plenty of fun bars and cheap bars. Sluggers World Class Sports Bar is a really fun bar in that part of town that has dueling pianos on weekend...