(1) Background: Today’s elite alpinists target K2 and Everest in midwinter. This study aimed to asses and compare weather at the summits of both peaks in the climbing season (Everest, May; K2, July) and the midwinter season (January and February). (2) Methods: We assessed environmental conditions using the ERA5 dataset (1979–2019). Analyses examined barometric pressure (BP), temperature (Temp), wind speed (Wind), perceived altitude (Alt), maximal oxygen uptake (VO2max), vertical climbing speed (Speed), wind chill equivalent temperature (WCT), and facial frostbite time (FFT). (3) Results: Most climbing-season parameters were found to be more severe (p < 0.05) on Everest than on K2: BP (333 ± 1 vs. 347 ± 1 hPa), Alt (8925 ± 20 vs. 8640 ± 20 m), VO2max (16.2 ± 0.1 vs. 17.8 ± 0.1 ml·kg−1·min−1), Speed (190 ± 2 vs. 223 ± 2 m·h−1), Temp (−26 ± 1 vs. −21 ± 1°C), WCT (−45 ± 2 vs. −37 ± 2 °C), and FFT (6 ± 1 vs. 11 ± 2 min). Wind was found to be similar (16 ± 3 vs. 15 ± 3 m·s−1). Most midwinter parameters were found to be worse (p < 0.05) on Everest vs. K2: BP (324 ± 2 vs. 326 ± 2 hPa), Alt (9134 ± 40 vs. 9095 ± 48 m), VO2max (15.1 ± 0.2 vs. 15.3 ± 0.3 ml·kg−1·min−1), Speed (165 ± 5 vs. 170 ± 6 m·h−1), Wind (41 ± 6 vs. 27 ± 4 m·s−1), and FFT (<1 min vs. 1 min). Everest’s Temp of −36 ± 2 °C and WCT −66 ± 3 °C were found to be less extreme than K2’s Temp of −45 ± 1 °C and WCT −76 ± 2 °C. (4) Conclusions: Everest presents more extreme conditions in the climbing and midwinter seasons than K2. K2’s 8° higher latitude makes its midwinter BP similar and Temp lower than Everest’s. K2’s midwinter conditions are more severe than Everest’s in the climbing season.