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Exclusive Chicago Singles Matchmaking Events. We put a tremendous amount of planning, preparation and work into our events, to ensure you have a good time and the opportunity to meet the kind of singles and potential partners you want to meet, and who share your relationship goals. Chicagoland Singles offers several ways to meet single people with the same interests as you. Join in the fun, do something you have never done before or always wanted to do. Life is about experiencing it, not regretting what you have never done or tried!