On a rainy holiday weekend, the city of Chicago and the sport of NASCAR celebrated the unlikeliest of marriages with a lakefront ceremony.

Chicago handled the decorations, with its soaring skyscrapers as the backdrop, as well as the catering, with Vienna Beef hot dogs, Garrett Popcorn and wedges of Lou Malnati’s deep-dish for sale.

NASCAR sent its drivers as the wedding party, roaring at up to 140 miles per hour toward the Field Museum before storming up Michigan Avenue, and booked music for the reception, though summer monsoons meant that The Chainsmokers and the country singer Miranda Lambert were canceled.

The yearlong engagement had been rocky at times, and there were plenty of doubters. NASCAR’s top series, after all, had never raced on city streets. And Chicagoans, many of whom care little about racing, worried about blocking off a huge section of downtown and snarling traffic for days. Still, for richer or poorer and through drenching downpours, Chicago gave its streets to NASCAR for racing, if only for the weekend.

“I certainly was pessimistic when it was first announced,” said Denny Hamlin, a longtime racecar driver who said that he had warmed up to the idea, and who was the fastest qualifier for the main race on Sunday. “When you see the fans that are walking around here on Saturday, their excitement of just seeing a NASCAR racecar up close, taking pictures, I mean, it kind of is like, this is what we’re supposed to do.”

In the end, Shane van Gisbergen, a New Zealand native competing in his first NASCAR Cup Series race, used his street course expertise to outlast the series regulars and finish first.

But the unyielding rain, which moved in on Saturday night and festered through Sunday, muted the festivities. Tarra Laux, a resident of Chicago’s South Side and first-time racegoer, said she enjoyed watching qualifying with her family on Saturday. But she was disappointed to see Ms. Lambert’s concert called off, and had wavered about whether to even return for the race on Sunday.

“We were hoping to come down here first thing this morning and go inside and spend a full day,” Ms. Laux said. They decided to go to the race anyway, but said the rain “kind of dampens everything.”

The NASCAR-ification of downtown Chicago — where stacks of fresh Goodyear tires rested on sidewalks, concrete barriers stood in front of bus stop shelters and the world-famous Art Institute served as a site for pre-race interviews — was a calculated risk.

NASCAR, which usually competes on built-for-racing tracks with straightaways and left turns, wants to diversify its fan base and introduce its sport to city dwellers. Chicago, whose downtown struggled through the coronavirus pandemic, wants to bring in new visitors and fill hotel rooms.

While the potential upsides were clear, so, too, were the costs of the 12-turn, 2.2-mile circuit along some of Chicago’s most iconic roadways. Arterial streets were closed for days, disrupting commutes and turning the Loop into a maze of barricades and traffic jams. Large sections of parkland were placed off limits to the public. Downtown residents were serenaded, lap after lap, by the body-shaking scream of three dozen racecars.

“It’s not even the race days, it’s the week before and the week after when everything is still shut down,” said Mary McNally, who works in marketing and lives near Grant Park. “It’s really inconvenient and forces you to change grocery stores and things like that.”

Plenty of other Chicagoans decided the race was a miscalculation. Rick Morrissey, a Chicago Sun-Times columnist, declared last week that “we’re not the people or the city” for this event.

“This is cultural, more than anything,” he wrote, suggesting that perhaps a Southern city with more racing history would be a better venue. “Maybe it’s a blue state/red state thing.”

Inside the course, where tickets started at $269, fans attending their first race took in the action alongside NASCAR die-hards whose T-shirts paid allegiance to their favorite drivers.

Audrey Prince, who lives on the West Side of Chicago, said she had followed NASCAR for years but never been to a race. Even amid the downpour, she said seeing stock cars zip up DuSable Lake Shore Drive was too unique to pass up.

“They’re racing on the actual streets that I’ve driven on and walked on,” she said, “so that right there alone is exciting.”

The weekend included tragedy and setbacks. A contractor at the track was electrocuted and died on Friday while final preparations for the race were underway. On Saturday, the first of the weekend’s two races was postponed midway through because of lightning, and then declared over amid a continuing downpour on Sunday that scrambled plans yet again.

NASCAR’s visit to Chicago had been the subject of intense local debate since Mayor Lori Lightfoot announced it last summer without involving residents or City Council members in negotiations. The future of the event grew more uncertain when Ms. Lightfoot was voted out of office this year. Though NASCAR’s contract with Chicago calls for three years of racing, the new mayor, Brandon Johnson, could move to cancel the deal.

Whether the city seeks a divorce will depend in part on metrics that are not yet fully known. NASCAR officials said that they expected up to 50,000 people a day at the event, and that they believed about 80 percent of ticket buyers were first-time racegoers. But the racing organization did not provide data on ticket sales, and as of Saturday afternoon, tickets were still available for purchase.

Several NASCAR drivers said they were aware of the disruption to the city but hopeful that the race would come to be seen as a win. The driver Bubba Wallace, who hosted a free racing-themed party last week on the South Side, said he had enjoyed his time in Chicago.

“You can walk down the streets a little bit and not get recognized, so I hear a lot of conversations,” Mr. Wallace said. “And a lot of people are on the fence about it. But you hear a lot of excitement, too.”

Robert Chiarito contributed reporting.

Mitch Smith and Jamie Kelter Davis

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