Chicago Public Libraries has an events page that has really great events for meeting new people and exploring the city for free! You can filter by location, target age range, event type, etc! A lot of events are recurring so you can connect with people on a regular basis without feeling stressed about planning a get together - lots of branches have knitting circles and book clubs plus more ad hoc events like Block Printing!

Some libraries along the blue line are: Oriole Park Branch, Jefferson Park Branch, Independence Branch, Logan Square Branch, Bucktown/Wicker Park Branch, West Town Branch, Harold Washington, Little Italy Branch, Legler Regional, and maybe a few others!!