Edit: if you search for "forget HSTS", you will see how hard it is to avoid this on some browsers.

For context, each of the retail locations of our company runs its own local MAMP server that serves a web app used all day by the employees on their tablets. It's accessible only on the LAN. Rather than have every employee need to know or type the local IP address for these (which change sometimes), we serve a centralized web page at http://ourcompany.com/employeeApp that just keeps a live list of the local (192.x.x.x) IP addresses harvested from each server in each location, and opens a connection to the local server in an iFrame. Because of what's now a hard ban on loading insecure HTTP content within an HTTPS page, we must serve that central iFrame wrapper page over HTTP. Unfortunately, we now need to give Chrome users a raw IP address for ourcompany.com, to avoid them being redirected infinitely to HTTPS and back.

[edit] I should add that the oddest thing is that it doesn't always overflow with redirects, and on a new device it often is able to go to the HTTP site. But once someone does type https:// or leave out the http:// by mistake, no level of cache clearing seems to remove Chrome's insistence on trying to force HTTPS on that page forever afterwards.

[edit2] The rationale for not setting up local DNS and SSL is that these servers are on all kinds of different local networks in stores around the country, are switched on and off by non-technical managers onsite, and I'm the author of the web app and the only tech support for it. It needs to be as simple as possible so that I'm not spending all my time tunneling into those servers, walking them through router problems and stuff like that.