Here’s one from the archives. The Chicago skyline seen from the St. Joseph / Benton Harbor area in Michigan, roughly 98 km (61 miles) across Lake Michigan. This is the furthest I've found for Chicago.
https://theviewshed.com/?view=10684
The lower parts of the skyline are hidden behind the horizon, but you can still see the tallest towers (Sears Trump, Hancock) peeking above the water, distorted by atmospheric refraction.
I’ve been collecting long-distance skyline views like this, both photographic and theoretical, and ended up building a site to organise them:
https://theviewshed.com
There are now around 2,100 records, all searchable by city, country, mountain, distance, and whether they’ve been photographed or not. There's a submission form on the site too if anyone wants add to the collection.