Hi,
Acapulco.co - High $xxx - low $xxxx (wait a little and it's higher. Personally, I think this is the weakest of these three.)
ChicagoHotels.co - Low $xxxx - Low-mid $xxxx (Keywords "Chicago Hotels" have an excellent sales history in every extension. Chicago goes great with Hotels. If you had something nice developed there and put some elbow grease in , you could easily command mid-high $xxxx)
Plotters.co - Keyword has some great advertising on Google (shows up 11 and that means a good market for this keyword). Great physical product name. Physical products almost always get nice prices. Plotter.nl sold for $3000 last month. Plurals are much nicer than singulars, in most cases.
I'd say mid $xxxx. If you wait and/or develop, could be more.