If you’re looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chokoloskee: The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 68°F. The rainiest months in Chokoloskee are August, June, July, and September, with each month seeing an average of 7 inches of rainfall.