The midfielder completed his maximum three-month stay from Derby with the 3-1 victory at Stevenage on Boxing Day.
But boss Robins is keen to see Bailey, 24, pull on a Sky Blue shirt once again in the new year, ideally after penning a transfer across the midlands.
"I'd like to sign James permanently but if not that then on loan again," Robins told Coventry's official website.
"But we will see what can be done and what we can do in January."
Prolific striker David McGoldrick also sees his loan stint come to an end on New Year's Day, with City still working on a possible deal with parent club Nottingham Forest although an agreement is looking increasingly unlikely.
On Monday Coventry took striker Leon Clarke on trial with a view to a permanent move next month.