The Boundary
1932 W. Division St.
Secluded booths for canoodling, a blazing fireplace—and if that doesn’t do the trick, the bar is bustling with singles.




Cru Café & Wine Bar
25 E. Delaware Pl.
It doesn’t get much more romantic than this cozy bar with a 300-bottle list—and a River North location convenient for happy-hour prowlers.




1325 W. Wrightwood Ave.
This intimate wine bar is owned by a woman (that alone is hot), attracts a female clientele (listen up, guys), and offers 30 or so wines by the glass.




Louie’s Pub
1659 W. North Ave.
Serenade your sweetie or woo a new love at this low-key karaoke bar. Embarrassing? Maybe. Sexy? Definitely.




Vertigo Sky
Dana Hotel, 2 W. Erie St.
Dizzying views, chic drinks, catsuit-clad servers; plus, you can check into a room for the night. Everyone wins.