Fly business class from Chicago to Naples with Alaska Airlines using mileage plan

The flights are nonstop between ORD and Naples International Airport (NAP). A booking fee of $19 applies along with 55,000 miles each way. Premium economy seats are available for 35,000 miles each way plus a $19 fee, while economy seats require 27,500 miles plus the same fee.

"August has the best availability in general," with more limited options in May and June. However, flexibility may allow travelers to find suitable flights during these months as well.

For those interested in accumulating more points for future travel on Alaska Airlines, credit cards such as the Alaska Airlines Visa Signature credit card or American Express cards that earn points on airfare purchases are recommended.

In summary, this offer allows planning ahead for a summer trip from Chicago to southern Italy by utilizing various point transfer options or purchasing additional miles with bonuses.