Noncheesy Loop Tour

Binoculars Tour by Chicago Elevated

There’s hidden beauty to be found in the steel and concrete canyons of the Loop. Second City alum Margaret Hicks will teach you to read the meanings behind the gargoyles, frescoes, and other way-up-high ornamentation on some of downtown Chicago’s most iconic buildings. The 90-minute tour starts at the Chicago Board of Trade. Plus: You get to keep the binoculars! $26.

Offbeat Museum

Money Museum

Highbrow it ain’t, but this museum on the first floor of the Federal Reserve Bank of Chicago is irresistibly entertaining. Try your hand at detecting counterfeit bills, see what a million dollars looks like (in the form of a giant cube of singles), and grab a free souvenir bag of shredded money—formerly worth $364—on your way out. Free. 230 S. La Salle St.,

Max Sansing mural
Photo: Max Sansing
Selfie Spot

Max Sansing Mural

Eye-popping street art meets a distinctly Chicago mythos in Sansing’s Woodlawn Works, one of more than a dozen murals the artist has made on the South Side. 66th Street and Dorchester Avenue

Souvenir Shop


Mag Mile T-shirt stores are for out-of-towners. This arty shop, with three smart-looking locations, traffics in more esoteric delights, from winsome silhouetted skyline necklaces to twee tea towels with an embroidered Chicago-style hot dog. 2958 and 5061 N. Clark St.; 2939 N. Broadway;

Underground Comedy


Ghoulish. Mystical. Grotesque. You're not at Second City anymore. Coproducer Sarah Sherman performs a bawdy form of standup alongside a lineup that includes noise musicians and performance artists who share her fixation on the unpretty aspects of the human body. (A bag of pubic hair is a recurring prop.) $7. The Hideout, 1354 W. Wabansia Ave.,

Pontoon boat
Photo: Jenn Winter
River Excursion

Chicago Electric Boat Company

Traditional double-decker tours are fine. But why cram shoulder to shoulder with strangers when you can pilot your own pontoon boat? These canopied watercraft, which can hold up to 12 people, are as easy to drive as a golf cart. Navigate as far upriver as you like. (Just return to the Loop dock on time.) $150 to $250 an hour, depending on boat size. 300 N. State St., Marina Level,

Staycation Hotel

The Robey

A five-point plan for capping off your big day: 1 Dip your toes in the rooftop pool at the breezy sixth-floor Cabana Club. 2 Enjoy the 180-degree view of the skyline. 3 Return to your tasteful, hardwood-floored guest room. 4 Slather yourself in Le Labo bath products. 5 Fall asleep thinking how nice it is that you don’t have to catch a plane home. Doubles from $405. 2018 W. North Ave.,