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For the moment the energy safety of the Kaliningrad region (KR) is largely dependent on the mutual electrical energy exchange through existing connections to Lithuania and further to Belarus and Russia. Taking into account the upcoming KR energy system disconnection from Lithuania, followed by isolated operation (starting from 2025) and wind energy potential of KR, the question of electrical production by the wind as an option for KR sustainable development should be considered. The paper aims to compare three different connection possibilities for onshore power plans (WPP) of different capacity (30 and 90 MW) based on preliminary system power flow calculations using an especially developed energy system model, which are: 1. connection of WPPs to the existing substations of the grid; 2. connection of WPPs to "Wind Grid" ("WG") – new lines and substations in energy system especially constructed for wind energy production; 3. simultaneous connection of WPPs to existing substations and to "WG". The conclusion of the paper is 1st the option is the cheapest, but not viable because WPPs create additional problems with voltage levels and lines overload. Some measures to overcome observed problems are proposed. The electrical system parameters, such as voltage levels, power flows, and power losses are very close for the 3rd and 2nd options. The 3rd option is more expensive, because of additional switching equipment, but most flexible and easy to handle for the system operator. [ABSTRACT FROM AUTHOR]