From a massive pile-up involving more than half of drivers on the NASCAR Chicago street course to a stunning tire mishap, wet roads and tight turns made for a crash-filled race in the historic downtown race.
Experts had predicted difficult conditions even before massive flooding and torrential rains added to the challenges for drivers competing in a first-of-its-kind event.
The 2.2-mile course took drivers speeding past iconic city landmarks and down major roadways, riddled with 90-degree turns - both left and right - and almost no room for error.
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The race was originally slated to be 100 laps, but was shortened to 75 as rain delays saw drivers racing to beat each other and the sunset.
None of that stopped Shane van Gisbergen from making Cup Series history in Chicago.
Here's a look at some of the many crashes spotted during the inaugural Chicago street race:
The overtime caution
Dillon's Wall
Michigan Avenue traffic jam
With just over 50 laps completed, a massive pile-up took out more drivers than any other crash in the race.
As the cars made the turn from Michigan Avenue onto Jackson Drive in turn 11, William Byron spun out and made contact with the barrier.
Both Kevin Harvick and Corey LaJoie then spun out trying to avoid his car, causing a backup of cars to begin. Byron then tried to get back on the track, closing off the one escape route going out of the turn.
Bowman and Hamlin spin out
Noah Gragson's Turn 6 nightmare
The sandwich
The tire barrier debacle
It only took three laps for the first caution flag to fly thanks to Kyle Busch.
Busch, who started the race in the 18th spot, was coming down Columbus Drive when he lost control of his vehicle heading into Turn 6, slamming into the tire barrier at the intersection of Columbus and Balbo Drive: