The Bering Strait oceanic heat transport influences seasonal sea ice retreat and advance in the Chukchi Sea. Monitored since 1990, it depends on water temperature and factors controlling the volume transport, assumed to be local winds in the strait and an oceanic pressure difference between the Pacific and Arctic oceans (the “pressure head”). Recent work suggests that variability in the pressure head, especially during summer, relates to the strength of the zonal wind in the East Siberian Sea that raises or drops sea surface height in this area via Ekman transport. We confirm that westward winds in the East Siberian Sea relate to a broader central Arctic pattern of high sea level pressure and note that anticyclonic winds over the central Arctic Ocean also favor low September sea ice extent for the Arctic as a whole by promoting ice convergence and positive temperature anomalies. Month‐to‐month persistence in the volume transport and atmospheric circulation patterns is low, but the period 1980–2017 had a significant summertime (June–August) trend toward higher sea level pressure over the central Arctic Ocean, favoring increased transports. Some recent large heat transports are associated with high water temperatures, consistent with persistence of open water in the Chukchi Sea into winter and early ice retreat in spring. The highest heat transport recorded, October 2016, resulted from high water temperatures and ideal wind conditions yielding a record‐high volume transport. November and December 2005, the only months with southward volume (and thus heat) transports, were associated with southward winds in the strait.