Woke up last Tuesday thinkin’ I’d finally tackle somethin’ useful—mappin’ out Chicago’s sketchiest boating spots. You know, places where the water goes from chillin’ to chompin’. Grabbed my notebook, life jacket, and this ancient waterproof camera I swear by. Headed straight for the lakefront before sunrise like some kinda obsessed coast guard dropout.

The Monroe Harbor Mess
First stop? Monroe Harbor. Looked peaceful enough at 5 AM, just some ducks paddlin’ around. Ha! Don’t trust it. Got close to the breakwall and bam—those underwater currents hit like a truck sideways. Nearly spun my lil’ runabout right into the concrete. Had to goose the throttle hard just to straighten out. Took notes shakin’: “Sudden whirlpool nonsense near wall. Keep distance or get wrecked.” Saw three faded hull scrapes on the stones—felt like readin’ tombstones.
Burnham Park’s Sneaky Wall
Next up, cruised south past Grant Park toward Burnham. Calm water, lazy waves… total trap. Saw a kayak couple pokin’ near the harbor entrance. Before I could blink, a freighter wake slammed ’em sideways into the seawall. No crunch thank god, but their paddles went flyin’. I yelled “MOVE!” like an idiot across the water. Scribbled in my soggy notebook: “Invisible wall + big boat wakes = flipped vessels. Guaranteed.” Felt like watchin’ a crash test dummy replay.
Belmont’s Deadly Jetty
Saved the sketchiest for last: Belmont Harbor jetty. Parked my boat 200 feet out, zoomed my camera in. Took maybe ten minutes to spot the pattern. Boaters tryna cut inside the red buoys? The lake laughs. Watched a pontoon drift too close—SUCK—got dragged sideways by some goddamn vortex machine hidin’ under the surface. Dude slammed reverse so hard his engine smoked. Added bullet points fer a reason:
- Jetty corners swallow boats like snacks
- Signage? Rusty little plaques ya need binoculars to see
- Currents shift faster than Chicago politics—trust NOTHING
Why Bother? ‘Cause We’re Dumb
Sat there bobbin’ in my boat, watchin’ four more idiots risk the jetty gap. Felt like screamin’. City keeps puttin’ up those “Danger!” signs made o’ toilet paper while the lake eats three boats a year here. My cousin’s bass boat got swallow-holed near Navy Pier last June. Took the Coast Guard 45 minutes to drag him out hypothermic. Know what changed? Nothin’. Just more faded buoys and shrugs. Wrapped up my notes feelin’ like some grim water detective: don’t trust calm water, don’t cut corners, and never ever gamble against a Great Lake. Packed up around noon—covered in spray, fingers pruney, but alive. Better than some. Damn right I’m double-knotting my life jacket next time.