Networking, public outreach, and transparency are important in the planning profession. This need for strong communication is necessary because there are usually many stakeholders with diverse interests - and colleagues with different skill-sets - involved in any given project.
Communication is also important because one cannot know everything, but someone in your network may know what you do not (especially if one knows a diverse group of professionals). Networking is helpful in learning more about how other fields complement your own. Hearing constructive criticism from people with different backgrounds on your own work (or from those in your field with more experience) can also be incredibly useful.
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Women in Planning and Development is a Chicago networking group that is full of friendly and accomplished ladies. They host events (for members and non-members alike) every month at which you can learn more about what others do and how they got there, as well as bounce ideas off of them.
The Commission on Chicago Landmarks usually meets on the first Thursday of every month about proposed local and national landmarks & districts and reviews permits of existing landmarks and contributing properties to historic districts. This is a great place to learn about newsworthy developments as (or even before) decisions are made.
For those interested in civic hacking (using open data sources to create user-friendly civic applications), Open Gov Hack Night is a great place to learn about what other organizations and techies have accomplished to make information more useful and convenient. It is even better if you are working on a project of your own! It is heavily attended by people with diverse professional backgrounds. Videos of past events are available online.
A similar event series is LISC's Data Fridays, which also provides information about recent projects that have deployed open data, or have demonstrations/workshops on how to use these tools. These events tend to be more intimate than Open Gov Hack Night.
Tuesdays at the APA is a monthly lecture at the American Planning Association (APA) Chicago offices, featuring speakers from around the country (and sometimes even further) about a range of topics. It is not necessary to be a member to attend. Lectures and powerpoints from previous events are available online. I highly recommend The Greenest Building, by Patrice Frey of Preservation Green Lab.
Moxie is a networking group for LGBTQA people in Chicago's planning related professions. Their field trips are very fun and informative!