Under global warming, Arctic sea ice has declined significantly in recent decades, with years of extremely low sea ice occurring more frequently. Recent studies suggest that teleconnections with large-scale climate patterns could induce the observed extreme sea ice loss. In this study, a probabilistic analysis of Arctic sea ice was conducted using quantile regression analysis with covariates, including time and climate indices. From temporal trends at quantile levels from 0.01 to 0.99, Arctic sea ice shows statistically significant decreases over all quantile levels, although of different magnitudes at different quantiles. At the representative extreme quantile levels of the 5th and 95th percentiles, the Arctic Oscillation (AO), the North Atlantic Oscillation (NAO), and the Pacific–North American pattern (PNA) have more significant influence on Arctic sea ice than El Niño–Southern Oscillation (ENSO), the Pacific decadal oscillation (PDO), and the Atlantic multidecadal oscillation (AMO). Positive AO as well as positive NAO contribute to low winter sea ice, and a positive PNA contributes to low summer Arctic sea ice. If, in addition to these conditions, there is concurrently positive AMO and PDO, the sea ice decrease is amplified. Teleconnections between Arctic sea ice and the climate patterns were demonstrated through a composite analysis of the climate variables. The anomalously strong anticyclonic circulation during the years of positive AO, NAO, and PNA promotes more sea ice export through Fram Strait, resulting in excessive sea ice loss. The probabilistic analyses of the teleconnections between the Arctic sea ice and climate patterns confirm the crucial role that the climate patterns and their combinations play in overall sea ice reduction, but particularly for the low and high quantiles of sea ice concentration.