Although not in Chicago here are some resources for spots and areas nearby.
Chicago Fun Club - a non-landed Nudist group
Chicago Area Nudist Sons - a non-landed Male Nudist Group
Check Meetup.com for more nudist groups forming.
Sun Ray Hills - Nude Resort - Burlington, WI
Valley View - Nude Resort - Cambridge, WI
Mazo Beach - Nude Beach - Sauk City, WI
Toadally Natural Garden - Naturist Farm - Hartford, WI
Sun Auro - Nude Resort - Roselawn, IN
Ponderosa - Nude Resort - Roselawn, IN
Lake O The Woods - Nude Resort - Valparaiso, IN
The Woodlot Nudist Retreat - Woodstock IL - research before going, sounds like owner may be hanging it up soon - there is an active group here on True Nudists that keeps in contact with him.
Check the other area groups here on True Nudists as they may have more ideas for you.

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