According to the rules you can post anything related to the Chicago area, so it’s probably just that their arn’t enough people on lemmy for a singe city community to have much other than news posts. Be the change you want to see in the community.
Post whatever you want! News posts are easy, so there's a lot of them, but anything with local interest fits. These communities just don't get a ton of traffic because Lemmy is so much smaller than Reddit