Otto Mezzo

Do you really want to end another late-night drinking session with cheap beer in a dive bar? May we suggest a wee-hours glass of amaro at Otto Mezzo instead. With a decor inspired by classic Italian cinema, and jewel-like cocktails that lean heavily on grappa and Italian liqueurs, this open-till-four (five on Saturdays) deco hideaway in River North makes last call feel languid and sophisticated, not desperate and sad. Plus: panini for sustenance! 311 W. Chicago Ave., ottomezzobar.com

The Infinite Wrench

For 28 years, the midnight performance of the Neo-Futurists’ Too Much Light Makes the Baby Go Blind was a rite of passage. Now the iconoclastic theater company is back with The Infinite Wrench, another Dadaist crazy train of supershort plays. The hyperenergized one-acts pack in more whip-smart social commentary and confessional pathos than you’ll find on a stage anywhere after—or before—midnight. From $10. Fridays and Saturdays at 11:30 p.m., Sundays at 7 p.m. Neo-Futurarium, 5153 N. Ashland Ave., neofuturists.org

Sabertooth at the Green Mill

This organ quartet has been playing the midnight-to-five gig on Saturdays at the Mill for a quarter century. That’s a lot of late nights—er, early mornings. The group attracts a menagerie of night owls, from insomniacs to hardcore jazz geeks. $5 until 2 a.m. 4802 N. Broadway, greenmilljazz.com

King Spa & Sauna

An after-hours visit to this suburban strip mall wonderland is truly transporting. A $45 admission entitles you to linger in the vast Asian spa for as long as you like, even overnight; services such as massages, facials, and body scrubs range from $50 to $150. A food court offering Korean soups and entrées stays open till midnight on weekends; it opens again at 8 a.m., so why not stick around for breakfast? 809 Civic Center Dr., Niles, kingspa.com/chicago

SmallFry

Griddle-crisp burger patties, a two-fisted fried chicken sandwich, thick shakes—these are the comforts the late-night palate craves. This tiny counter-service joint’s pièce de résistance? Triple-cooked fries dusted with a house version of Doritos Cooler Ranch seasoning. 2489 N. Milwaukee Ave., smallfry.me