I lived in Chicago for six years and still visit often.
I'm pinging you, Borges, since you live in Chicagoland and you can vouch that if you are ever looking for a 9/11 Truther or a Dennis Kucinich supporter or a militant vegan in Chicago, your best bet is Wicker Park.
In the last decade or so, Wicker Park has been renovated and reclaimed and is now a haven for ‘free-spirited’ twenty-somethings. Politics aside, it’s a lovely neighboorhood with some great historic homes going back to the turn of the century.
Actually, I’d say Rogers Park or any number of other neighborhoods are more leftist but Wicker Park tries to be the contrarian/infantile/outre capital of Chicago. It’s denizens strike not so much a leftist ideological as a bizarre-chic “look at how goofy I can be” pose.
Perfect for the Sankt Pauli gals, dontcha think?