Over the last about four decades, coinciding with global warming and atmospheric CO2 increase, the extent and thickness of Arctic sea ice has decreased dramatically, a decrease much more rapid than predicted by climate models. The driving forces of this change are still not fully understood. In this context, detailed paleoclimatic records going back beyond the timescale of direct observations, i.e., high-resolution Holocene records but also records representing more distant warm periods, may help to to distinguish and quantify more precisely the natural and anthropogenic greenhouse gas forcing of global climate change and related sea ice decrease. Here, we concentrate on sea ice biomarker records representing the penultimate glacial/last interglacial (MIS 6/MIS 5e) and the Holocene time intervals. Our proxy records are compared with climate model simulations using a coupled atmosphere-ocean general circulation model (AOGCM). Based on our data, polynya-type sea-ice conditions probably occurred off the major ice sheets along the northern Barents and East Siberian continental margins during late MIS 6. Furthermore, we demonstrate that even during MIS 5e, i.e., a time interval when the high latitudes have been significantly warmer than today, sea ice existed in the central Arctic Ocean during summer, whereas sea ice was significantly reduced along the Barents Sea continental margin influenced by Atlantic Water inflow. Assuming a closed Bering Strait (no Pacific Water inflow) during early MIS 5, model simulations point to a significantly reduced sea ice cover in the central Arctic Ocean, a scenario that is however not supported by the proxy record and thus seems to be less realistic. Our Holocene biomarker proxy records from the Chukchi Sea indicate that main factors controlling the millennial Holocene variability in sea ice are probably changes in surface water and heat flow from the Pacific into the Arctic Ocean as well as the long-term decrease in summer insolation. Here, increased Pacific Water inflow (and heat flux) may have triggered the contemporaneous decrease in sea ice and maximum surface-water productivity during mid-Holocene times.