A cold air outbreak (CAO) is an extreme weather phenomenon that has significant social and economic impacts over a large region of the midlatitudes. However, the dynamical mechanism of the occurrence and evolution of CAO events, particularly the role of the stratosphere, is not well understood. Through an analysis of one extreme CAO episode that occurred on 27–31 January 2019 across much of the US Midwest, this study examined its thermodynamic structure and the impact of stratospheric downward transport using the single-field-view (SFOV) satellite products (with a spatial resolution of ~14 km at nadir) from the Cross-track Infrared Sounder (CrIS) onboard Suomi National Polar-Orbiting Partnership (SNPP) in conjunction with MERRA-2 and ERA-5 reanalysis products. It is found that along the path of cold air transport, particularly near the coldest surface center, there exists a large enhancement of O3, deep tropopause folding, significant downward transport of stratospheric dry air, and a warm center above the tropopause. The upper warm center can be observed directly using the brightness temperature (BT) of CrIS stratospheric sounding channels. While similar large-scale patterns of temperature (T), relative humidity (RH), and ozone (O3) are captured from CrIS, MERRA-2, and ERA-5 products, it is found that, in the regions impacted by CAO, MERRA-2 has a thicker dry layer under the tropopause (with the difference of RH up to ~10%) and the total column ozone (TCO) from ERA-5 has a relatively large positive bias of 2.8 ± 2.8% compared to that measured by Ozone Mapping and Profiler Suite (OMPS). This study provides some observational evidence from CrIS that confirm the impact of the stratosphere on CAO through downward transport and demonstrates the value of the SFOV retrieval products for CAO dynamic transport study and model evaluation.