Despite the growing popularity of Long Range (LoRa) wide area networks (WANs), there is limited research on the antennas' influence on a node's connectivity. In this paper, the channel gain of an 868 MHz LoRa-Wan node in an urban environment is used to evaluate the performance of different antennas, as well as evaluate motion, elevation, and shadowing effects on the nodes connectivity. A dual-transmitter node with two tightly-coupled antennas is utilized to characterize the channel gain between the antenna-under-test, and multiple indoor and outdoor gateways over 1 km away, through the received signal strength indicator (RSSI). It is demonstrated that using a broadband UWB-inspired monopole implemented on an inexpensive cardboard substrate, the channel gain can be improved over commercially available whip antennas.