Urban abseiling is the dumbest, most electric thing I’ve done since moving back to Chicago last spring, and I’m still picking gravel out of my palms to prove it. I’m perched on my Wicker Park fire escape right now, legs dangling over a drop that feels way too much like the rooftops I’ve been flinging myself off, wind smacking Lake Michigan chill straight into my face. Seriously, the first time I clipped in on a 12-story parking garage in the Loop, I legit whispered “don’t puke” like the rope could hear me. Anyway, here’s the unfiltered dump from a guy who’s turned city rooftops into his very questionable playground.
Why Urban Abseiling Is My New Mid-Life Crisis
Look, I’m 34, I eat too many hot dogs, and I thought “extreme” meant ordering extra giardiniera. Then my buddy Dragos—yes, that’s his real name, he’s Serbian and built like a fridge—dragged me to a rooftop rappelling meetup above a shuttered bank. The view? Sears Tower stabbing the sky, El trains rattling like toys. I smelled diesel and pretzels and my own fear-sweat. Clipped in, leaned back, and—plot twist—my left shoe untied itself halfway down. Spent the last 30 feet praying the lace wouldn’t wrap the rope. Landed, untangled, and laughed so hard I snorted. That’s the drug, man.
Gear Checklist From a Guy Who Forgets His Own Birthday
- Harness: Mine’s a beat-up Black Diamond I bought off some climber dude on Facebook Marketplace. Still smells like his van.
- Rope: 9.8mm dynamic—bright orange so the cops spot me before I hit the sidewalk.
- Helmet: Mandatory unless you want your mom yelling from Ohio.
- Snacks: Pro tip—don’t bring deep-dish in your chalk bag. Grease + chalk = slippery disaster. Ask me how I know.
Picking Your Urban Abseiling Playground (Without Getting Arrested)
Chicago’s got gems if you squint past the “no trespassing” signs. The old post office on Van Buren? Abandoned, 14 stories, and the graffiti down the stairwell is straight art. Just… don’t Insta-story your entry point, cool? I once sweet-talked a security guard with a half-melted Italian ice. Worked until his boss showed up. Pro move: go at 5 a.m. when the city’s still snoring off last night’s regrets.
H3: My Favorite Chicago Urban Abseiling Drops
- Marina City corn cobs – those round towers? Curved walls mean you swing like Tarzan if the wind kicks.
- Aon Center ledge – legal(ish) with a permit through a climbing gym, but the glass reflects your terrified face back at you.
- Random West Loop warehouse – zero permits, max adrenaline, and a dumpster landing softer than my mattress.
The Time Urban Abseiling Almost Ended Me (Okay, Dramatic)
Picture this: 22 stories up a condo in Streeterville, sun setting, Lake Michigan doing that glittery thing. I’m flowing down smooth—then my ATC jams. Rope locks. I’m dangling like a piñata while a brunch crowd below sips mimosas and films me. Took 20 minutes of wiggling, cursing in three languages I don’t speak, and finally cutting a sling to free it. Lesson? Double-check your damn device before you yeet off the edge. My GoPro died mid-scream—small mercies.
Safety Tips From a Dude Who’s Still Here
- Buddy system: Solo urban abseiling is just expensive suicide. Bring Dragos.
- Check weather: Chicago wind will slap you into a billboard advertising erectile dysfunction meds. True story.
- Know the law: Some cities (cough, NYC) will fine you into next week. Chicago’s chill if you’re discreet and don’t break windows.
- Backup plan: Always rig a second rope. I learned that after the jam incident—now I’m paranoid in the best way.
The Afterglow (And Bruises) of Rooftop Rappelling
Touching pavement after a clean descent? It’s better than sex and deep-dish combined. Your legs shake, your heart’s doing dubstep, and you smell like tar and victory. I keep a Polaroid of every drop taped inside my closet—proof I’m not totally wasting my 30s. Some nights I scroll them while eating cold Giordano’s on this same fire escape, wind whipping, wondering which rooftop I’ll hit next.
Final Ramble: Go Clip In, But Don’t Be Me
Urban abseiling turned my concrete jungle into a playground, but I’ve got the scars and one missing eyebrow to prove it’s not a joke. Start small, train with pros (shoutout to Chicago Adventure Club for not laughing when I cried), and maybe skip the pizza. If you’re in the US and itching for city abseiling that’ll rewrite your pulse, DM me your dumbest fear—I’ll talk you off the ledge, or down it. Just promise you’ll send me the video when you scream.
