Late-night drinking

Around Town editor Madeline Nusser lives up to her title by traversing the city all night—and even outlasting the strippers.

Midnight I receive a text from a friend: “Begin night at Rainbo?” (1150 N Damen Ave, 773-489-5999).

12:05am Throng of hipsters smoking outdoors makes it difficult to reach Rainbo’s door; suburbanites indoors make it difficult to reach the bar.

12:15am My friend saunters off to another watering hole, while my boyfriend and I opt for bowling at Lincoln Square Lanes (4874 N Lincoln Ave, 773-561-8191). Sixtysomething locals park it at the bar while the lanes brim with twentysomethings.

1am Boyfriend bowls 200-plus; I struggle to break 75. A stream of $3.50 Coronas cures sore-loseritus.

1:20am The young bowlers beside us realize that a jukebox controls the music. Kelly Clarkson ensues.

1:45am After I suffer a third loss, we depart to River North’s Redhead Piano Bar (16 W Ontario St, 312-640-1000). The valet sets us back $15, after which we spot plenty of free parking. Ouch.

2:15am We sidle up to the piano to watch Redhead performer David Scott Crawford. A sea of immaculately coiffed heads drunkenly bobs to “Rocket Man” two seconds behind tempo.

2:30am After discovering the “song menu,” I request the most depressing tune, just for kicks. I slip $5 into a napkin on which I’ve scrawled NEIL YOUNG’S “OLD MAN.”

2:45am I order a $9.50 Dewar’s, eschewing the cocktail menu of flirtinis and cougartinis.

2:53am Overheard from sloshed cougar: “He’s a pianist, but I call him penis. Don’t worry—I know him.”

2:55am We duck out for cocktails at the Drawing Room (1 E Oak St, 312-255-0022), the restaurant tucked behind the trendy Oak Street club Le Passage.

3:10am Both the Sazerac and the tequila drink infused with apple butter are delicious.

3:15am People are copulating lap dancing in the corners.

3:35am Starving, we head to Lakeview Golden Nugget (2406 W Diversey Ave, 773-252-8903).

4am Waitress Mary repeatedly says sweetie while delivering yummy butter-saturated toast. “Hey, sweetie. Here ya go, sweetie. Check, sweetie? Thanks, sweetie. Bye, sweetie.”

4:30am Still hungry, we decide to sate our curiosity about whether the ads touting the “hot buns” at the fully nude strip club Admiral Theatre (3940 W Lawrence Ave, 773-478-8111) mean literal sticky buns.

4:35am Nope.

5:30am Even the strippers are going home. We exit the club, which looks beautiful bathed in sunlight.

NEXT>>