In light of the rapid Arctic warming and continuous reduction in Arctic Sea ice, the complex two-way Arctic–midlatitudes connection has become a focal point in recent climate research. In this paper, we review the current understanding of the interactive influence between midlatitude atmospheric variability and Arctic Sea ice or thermal conditions on interannual timescales. As sea ice diminishes, in contrast to the Arctic warming (cooling) in boreal winter (summer), Eurasia and North America have experienced anomalously cold (warm) conditions and record snowfall (rainfall), forming an opposite oscillation between the Arctic and midlatitudes. Both statistical analyses and modeling studies have demonstrated the significant impacts of autumn–winter Arctic variations on winter midlatitude cooling, cold surges, and snowfall, as well as the potential contributions of spring–summer Arctic variations to midlatitude warming, heatwaves and rainfall, particularly focusing on the role of distinct regional sea ice. The possible physical processes can be categorized into tropospheric and stratospheric pathways, with the former encompassing the swirling jet stream, horizontally propagated Rossby waves, and transient eddy–mean flow interaction, and the latter manifested as anomalous vertical propagation of quasi-stationary planetary waves and associated downward control of stratospheric anomalies. In turn, atmospheric prevailing patterns in the midlatitudes also contribute to Arctic Sea ice or thermal condition anomalies by meridional energy transport. The Arctic–midlatitudes connection fluctuates over time and is influenced by multiple factors (e.g., continuous melting of climatological sea ice, different locations and magnitudes of sea ice anomalies, internal variability, and other external forcings), undoubtedly increasing the difficulty of mechanism studies and the uncertainty surrounding predictions of midlatitude weather and climate. In conclusion, we provide a succinct summary and offer suggestions for future research.