Tim Walz and JB Pritzker are doing great but in a more midwestern way.

boystown and andersonville are the most well known ones, there's a great scene in Buena Park and my personal favorite so far is in Logan Square+Avondale

they're both great. i prefer chicago because there are multiple different trans communities/sub-communities, trans-friendly nightlife is more available and the public transit makes it super easy to get around.