I have spent many hours looking for a solution before beginning this thread on ET.
I have observed that Chicago was a very expensive location for a VPS, compared to other cities.
I want to avoid AWS, Google and the like. Unless you pay large subscriptions, you get a low-end black box system located anywhere.
https://lowendbox.com/tag/chicago/ : interesting site, but nothing good at the moment
https://www.colocrossing.com/ : no VPS service
https://www.serverhub.com/dedicated-servers/chicago : globally cheap, but not cheap for Chicago
https://chartvps.com/ : globally cheap, but not cheap for Chicago
https://www.speedytradingservers.com/prices/ : expensive
https://www.steadfast.net/chicago-managed-trading-servers : price not available (probably ridiculously high)
http://www.theomne.net/virtual-private-servers/ : OK for when I'll start my hedge fund

, but expensive for the tests I want to run
So far, the best solution I heard of for Chicago is :
https://budgetvm.com/kvm-windows-vps.php at 45$/month.
As a post scriptum, I would suggest to Europeans (and non-Europeans as well !) interested in VPS (not for trading) to go check this super cheap yet great value provider located in Germany :
https://contabo.com/?show=vps