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Your one stop for singles in the Prairie State of Illinois. Browse our Illinois personal ads, send an email and start a relationship with your match. Browse our Winnetka personal ads, send an email and start a relationship with your match. Online Dating 101: Step one, create your free Match.com Winnetka personal profile with your best photo; step two, watch your Winnetka dating choices line up; step three, choose the date of your dreams.