In one picture tweeted by a resident, the roof dangled over the side of a brick apartment building.
"Pretty sure my roof is supposed to be more on the roof. #WindyCity," Michael Lansu tweeted, with a photo of torn roofing material and what appeared to be broken plywood.
A wind advisory was issued for much of the Midwest near the Great Lakes on Friday, and communities in the greater Chicago area saw gusts often reach more than 60 mph and even 72 mph in one spot, the National Weather Service said.
Meanwhile, gales whipped the open water off Chicago at 63.6 knots. A gale warning will last through Saturday with waves reaching 10 to 20 feet in parts of Lakes Michigan, Huron and Ontario through Saturday, the service said.
"A high volume of outage calls" overwhelmed ComEd, the electric utility said on Twitter. At least 114,000 people were without power at one point, with at least half of those blackouts in Chicago, CNN affiliate WLS reported.
O'Hare International Airport reported more than 160 flight cancellations and delays up to 50 minutes, the facility said on Twitter.
Commuter train service in the city was also disrupted due to debris on tracks in some locations, the Chicago Transit Authority said.
There were no immediate reports of injuries, despite the apparent damage.
Residents and motorists recounted the terrifying winds on social media, with photography of the damage.
Truck driver David Warren was knocked off the road, and his semitrailer landed on its side in the dirt beside Interstate 35 near Ellsworth, Iowa.
"I come into this clearing and the gust of wind just picked me up and brought me over and set me on my side, and I mean there was no stopping it once it started. It just picked me up and threw me right over like I was a piece of trash on the side of the road," Warren told CNN affiliate KCCI.
In another incident, a ferocious wind toppled a canopy that would normally protect motorists at the pump.
"Touhy and Elmhurst! Wind toppled over Marathon overhang!" Chicago area resident Joseph Bittolo tweeted
Buildings in downtown Chicago were evacuated apparently because flying debris from nearby construction sites broke windows, WLS reported.
The blustery weather was caused by strong southwest winds in association with a strong low pressure area to the north of Chicago.