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Considering the weather conditions.
The best season to travel to Cuba is the “winter” time (November – April), because the temperatures are not so high as in summer (May- October) but still warm enough to enjoy the beach. At this time of the year, the temperatures usually are between 23 and 32 degrees Celsius (approximately at the day time) and between 15 and 27 degrees Celsius (approximately at night). At north-western part of the island, between November and February some cold fronts coming from the North American continent can bring the temperatures for a few days ( average 3 or 4 days ) under 15 degrees Celsius. For that reason, we recommend you to take with you a light jacket if you travel during this period.
During the summer time the temperatures can easily reach 33 degrees Celsius and even higher in some parts of the country, and the relative humidity is average 80 %. 
Winter time is also the dry season in Cuba with less than 40 % of the rain falls, which is very important because it helps to reduce the relative humidity on the air which is average 80 % on the summer.
The hurricane season in Cuba is between June and November, with a peak between September and October. But in November the hurricane strikes are seldom.

Considering planes tickets and hotel prices.
The high season in Cuba is mainly during winter season in Europe and North America, but inside of every season, there are some months that the airline tickets are generally more expensive than others.

Below are some examples:
These months are usually less expensive

  1. January
  2. February
  3. October
  4. November

These months are usually more expensive

  1. June
  2. July
  3. August
  4. December

Eastern and summer holidays periods can be expensive if you do not book your holidays a while ahead.