I’m riding south on Damen on Saturday, May 30 of this year at roughly 2pm, and at the intersection with Lake Street when I see flashing lights and sirens travelling east at twice the speed limit. Maybe five-dozen police cars and SUVs pass me in a tight line, headed for the Chicago Loop, I assume.
I’d been planning to go downtown anyway just to enjoy the empty roads during the Covid lockdown, so even though I should know better I followed the cop cars into downtown.
I see a few protesters on my way, but the streets are mostly empty. Usually protests start at Daley Plaza because it’s a broad neutral space in shouting distance from the court house and other municipal buildings, but today the area two blocks from Daley Plaza in all directions is shut down by police-car-barricades. The city buses I traveled down Lake with reroute south, and I turn north.
I wiggle around the streets, looking at buildings and getting lost in the desolate grid that’s normally filled with cars and tourists around this time of year, until I end up on Dearborn, the main 2-way cycling corridor through the loop, just north of the empty Daley Plaza. Downtown is not only empty, but its quiet too – no car honks, no heavy machinery; for the first time ever I can hear birds and the shifting of gears as I’m passed by a young man on a Divvy Bike.
I follow him north to the river as a general din rises somewhere ahead of me, hidden by buildings but echoing through the man-made canyon. In the sunlight by the river I see thousands of protesters spread out all over the river walk, loosely circling Trump Tower.
The streets are not shut down, and I see car-driving gawkers caught in unmoving traffic, swarmed by pedestrians. There’s a small crotch-rocket gang set up in the middle of Wacker Drive in front of the Hilton. I also see college-age white guy with dreadlocks who took way too much drugs sitting on a bench, completely unfocused, like this is fucking Lollapalooza.
I didn’t take many pictures because the entire event had a negative charge around it, and I wasn’t eager to hang there too long. The area was peaceful, not even particularly loud, but peeking under legs I’d see some kid spraypainting a wall, or I’d see some Trustafarian knock over a trashcan. A few rocks got thrown, and I heard a few calls for “MEDIC!” in the crowd. In the distance I saw they raised the Dusable drawbridge, and I assumed they’d soon be doing that to the other bridges to separate the protests into two groups.
After just a minute or two of spectating I got back on Dearborn, went across the river, and sojourned back home on nearly vacant streets, occasionally passed by speeding cop cars. Regular bouts of “chop-chop-chop” above signaled the refueling shift changes for the police helicopters that traced my route back to the northwest side.
Over the night things got violent, I heard, and a curfew was instituted for 9pm. The Wall Street Journal reported 240 arrests and one shooting death. WBEZ reported 669 arrests and 30-something police injuries. Block Club has some numbers too. The details are still coming out.
The looting spilled out out downtown, hitting commercial districts all over the city, including the Wicker Park shopping district, just a few blocks from my house.
Sunday morning I decided not to go on a bike ride while eating breakfast on our front stairs, watching police cruisers swarm and disperse on the main road, which must have been their rally point.
This post in ongoing, but I wanted to get something out there so curious people could know a little more about the situation in the city.


