It looks like there is both the Chicago Area REIA careia dot org and the Chicago REIA groups chiacgoreia dot org (this one is the Andrew Holmes one).Typically they will let you come to a meeting or two before joining, so you can get a taste of what they are all about. 

I am new to real estate investing as well and have decided to go the house hacking route to get my first taste of what real estate investing feels like.

I think that is the biggest knot i have to loosen because I am using private money for my first few investments, hopefully just the first one so I can enjoy the taste of tax benefits. 

This alone may result in some RE price declines.Too risky for my taste. 

You could do interest-only payments so they get a small taste every month. 

After purchasing the home for $119,000 (negotiated the sales price down from $130,000, we pushed in about $22,000 cash to update the entire interior and exterior of the home - nothing fancy, but tasteful and simple!

Being in Philly, you are about 2 hours from Baltimore and that seems too far to go to own rental properties for my taste.

Remember that the bitter taste of having a bad deal (especially when you're living in it) will last a lot lot longer than any time or money wasted pursuing that deal. 

The live in flip scenario was the most accessible way for me, and being as you're still young, it's worth sacrificing some time, house hacking a bit, living for free, getting a taste of renovating a home, and then continuing your journey from there. 

Also, it gives you the taste of screening tenants, handling repairs (either self performing or subing it out), rent collections, Property management, etc.