Dating in Chicago: Insider's Guide

325 W. Huron, Chicago, IL 60610 (map)

Friday and Saturday at 11pm, tables come off and the DJ comes on, spinning Latin tunes for dancing until 2am.

170 N Dearborn St, Chicago, IL 60601 (map)

The Goodman complex also includes an Italian restaurant, Petterino's.

418 Sheridan Rd, Highland Park, IL 60035 (map)

Food and drink prices inside Ravinia are high--you're better off bringing your own.

2100 N Halsted St, Chicago, IL 60614 (map)

Red Rooster has a charming, reasonably priced selection of about 50 wines, mostly French and most in the $20-$35 range. Several glasses priced at $5-$6.

505 N Lakeshore Dr, Chicago, IL 60611 (map)

The banquettes facing the windows put you side-by-side with your dining partner, but provide the best views.

1480 W Webster Ave, Chicago, IL 60614 (map)

Every other Wednesday evening at 7:30pm, you can indulge in a tasting of 12 to 16 wines from different regions along with appetizers for $30-$50.

1616 N Wells St, Chicago, IL 60614 (map)

Tickets for the Monday night performance of the National Touring Company's "The Best of Second City" are $8. There are no other student or senior reduced-rate tickets.

340 W Armitage Ave, Chicago, IL 60614 (map)

Accomplished flamenco guitarist Ted Richine has been serenading Geja's customers for more than 20 years.

111 S Michigan Ave, Chicago, IL 60603 (map)

Free admission all day Tuesday.