You should be able to. In the past when they were running 500 kW they were easily heard in the Chicago area on regular basis.
The difference now is that TWR is going to have several very directional antenna systems, one aimed at Cuba and the other at the Brazilian Amazonia. When on the Cuban array, we can assume that the main lobe is going to be directed from Bonaire to that island, and that means the peak value would be towards the Des Moines to Chicago arc.