Most major cities worldwide are affected Urban Heat Islands – a condition of relatively higher temperatures being observed in one area compared to another that can be caused by a decrease in greenspace. One of the major reasons attributed to this increase in the warming of urban landscapes is the decrease in green space. This concept has received a lot of attention due to the destruction of vegetation for urban development and has prompted long-term spatial-temporal studies of Urban Heat Islands to understanding local climates. The objective of this study is to use Landsat data to examine the temporal intensification of UHIs and their variability from 1984–2016 for the cities of Chicago and Minneapolis-St. Paul. Landsat L4-5 TM), L7 ETM+), OLI and TIRS from 1984 to 2016 was used to examine land surface temperature (LST). Firstly, we converted the digital number (DN) to spectral radiance (L) and to temperature in Kelvin and from kelvin to Celsius and a conversion from Radiance to Top of the Atmosphere Reflectance and estimation of land surface emissivity. Finally, LST was estimated and Urban Heat Island retrieval and anomalies computed to help examine inconsistencies in our data. Our analysis showed year-to-year fluctuations in surface temperature, intensification of UHIs for both metro areas. Using a defined deductive index to identify environmentally critical areas, estimates of UHIs based on LST showed that both metropolitan areas are UHIs with LST > µ + 0.5 × δ. Higher intensification values were observed in 1988 and 2010 for Chicago and 1984, 1999 and 2016 for Minneapolis-St. Paul from analysis. While both areas have the similar climatic conditions, our analysis show differences in UHIs intensification as observed in their urban growth patterns. Chicago experiences a higher UHI intensity compared to Minneapolis-St. Paul and this could be explained by higher number of tall buildings than Minneapolis-St. Paul.