Start with dinner at Aria (200 N. Columbus Drive, 312-444-9494), where there's a special, three-course prix-fixe dinner ($43 per person) available before 7:30 p.m.
Then, what could be more romantic—not to mention sensual and seductive—than a dance concert? River North Chicago Dance Company performs its annual Valentine's Day weekend engagement at 8 p.m. at the nearby Harris Theater (205 E. Randolph St., 312-334-7777; $30-$65). A trio of new works include Frank Chaves' "Tuscan Rift," set in part to music by popular Chicago songster Andrew Bird, and Monique Haley's high-energy "Uhuru." A revival of Robert Battle's thunderous, runaway "Train" is also on the bill.
For dessert, there should be just enough time to dash over to Millennium Park's Park Grill (11 N. Michigan Ave., 312-521-7275) open until 10:30 p.m. on weekends.