Dec. 30: Relish the end of the holiday season and extend your New Year’s Eve festivities from one night to two at the 19th annual Eve of the Eve celebration. Don your black-tie best and mingle with more than 2,000 young professionals in Union Station’s Great Hall, where there will be no shortage of hors d’oeuvers, cocktails and dancing to live music from local bands Pat McKillen and South of 80. Proceeds from the event will benefit HighSight, which helps raise money for scholarships, tutors and college readiness programs that help students attend and excel at Chicago private high schools. 8 p.m. to 1 a.m. VIP tickets $150, standard tickets $125 in advance or $140 at the door. 500 W. Jackson, Highsight.org.