Are you ready to discover a single person that is looking to find a someone like you? Or do you only want a new friend to go with to watch the sunset and share a bottle of wine with this weekend? Zoosk makes it easy for you to connect with Chicago singles to date. Online dating helps you branch out into social circles that you haven't encountered yet. Sign up now and upload your picture. Chicago singles want to meet you! Date smarter. Try Zoosk online dating.