The annual event, which focuses on strengthening police-community partnerships, turned the area outside the Evanston Police Department into a neighborhood block party.
One of the night's biggest attractions was the dunk tank, where attendees lined up for a chance to send the police chief into the water.
"I thought you liked me!" the chief joked after being dunked.
Families said the event offered children an opportunity to interact with police officers and first responders outside of emergency situations.
"We're having a really nice time. We got to see the chief dunked in the dunk tank, which was really fun," attendee Adam Kahn said.
His daughter, Lizzie Kahn, also enjoyed the experience.
"I really like getting a lollipop and watching the Chief get dunked," she said.
Attendee Thomani Klamm said the event's block-party atmosphere felt right at home in Evanston.
"We love block parties. I feel like that's quintessential Evanston summer is going to a block party," Klamm said.
The community-building effort extended beyond Evanston. Chicago police held National Night Out events in all 22 police districts, with Interim Superintendent Fred Waller and Mayor Brandon Johnson in attendance. In Burr Ridge, children hopped aboard a miniature train as families gathered for an evening of food, fun and face-to-face time with first responders.
Klamm said events like National Night Out help children become familiar with police officers before they encounter them during an emergency.
"That's so important to me as a mom, because if they see a familiar face or see someone they've known from a friendly activity, like, they're more likely to respond," she said.
Evanston police officers said relationship-building remains a key part of their work.
"We're in the business of people like this is what we do is work with people, connect with people. Is it our job to understand people? So, to be able to have people at our house in this way is special and significant," Sgt. Enjoli Daley said.
Sgt. Tosha Wilson said strong relationships between police and residents benefit the entire community.
"When you have great connection with your police department and the police department with the community, it's an automatic win," Wilson said.
Organizers said they hope the conversations and connections made during National Night Out continue long after the event ends, helping turn familiar uniforms into familiar faces.