Leisure

Love Shacks

The Best Hotels for Extracurricular Relations

Discretion. Some people have it. Some people are Anthony Weiner. So in the interest of keeping secrets secret, we thought we’d remind you of some inconspicuous, but very plush, hotels where you and a friend can, um, hang out... without calling too much attention to yourselves. Unless you post the pictures.

1920s Opulence on Delaware
GOLD COAST

1920s Opulence on Delaware

The Place: The Talbott Hotel.
The Risk: Medium.
The Reward: A close-to-the-Loop (but not too close) rendezvous point with a nice couples package: suite upgrade, rose petals on the bed and monogrammed robes. Which, naturally, you should immediately burn.
The Alibi: You were just having lunch at Little Market Brasserie in the lobby.

A Romantic Interlude near Wrigley
LAKEVIEW

A Romantic Interlude near Wrigley

The Place: The Majestic Hotel.
The Risk: Medium.
The Reward: A mahogany-paneled palace tucked away on a quiet little stretch. Offering chocolate-covered strawberries, champagne, flowers and ballpark proximity.
The Alibi: You were so tired after the Cubs game that you needed a place to sleep off your Budweiser.

A Room with a View of Michigan Avenue
STREETERVILLE

A Room with a View of Michigan Avenue

The Place: Ivy Boutique Hotel.
The Risk: High, but not quite Weiner-esque.
The Reward: A narrow high-rise that’s hidden in plain view. With platform beds, a fully stocked bar and in-room massages.
The Alibi: You were just grabbing a martini at Sky Terrace, the rooftop bar. You don’t know where the masseur came from.

Italian Sexiness on Halsted Street
LINCOLN PARK

Italian Sexiness on Halsted Street

The Place: Villa D’Citta.
The Risk: Low.
The Reward: A secluded B&B disguised as a Tuscan villa, complete with an indoor hot tub, a king-size, rose-petal-strewn bed and a fireplace.
The Alibi: You were just looking for a place to practice your Italian.

A Historic Mansion in the South Loop
NEAR SOUTH SIDE

A Historic Mansion in the South Loop

The Place: The Wheeler Mansion.
The Risk: Medium.
The Reward: A fully restored, pre–Great Chicago Fire manse. With claw-foot tubs, four poster beds and ironing services. Just in case your shirt becomes wrinkled at some point.
The Alibi: Your passion for Chicago history is unquenchable.

Elsewhere on the Daddy

More Leisure in Chicago