Mesoscale convective systems (MCSs) are frequently observed over the U.S. Great Plains during boreal spring and summer. Here, four types of synoptically favorable environments for spring MCSs and two types each of synoptically favorable and unfavorable environments for summer MCSs are identified using self-organizing maps (SOMs) with inputs from observational data. During spring, frontal systems providing a lifting mechanism and an enhanced Great Plains low-level jet (GPLLJ) providing anomalous moisture are important features identified by SOM analysis for creating favorable dynamical and thermodynamic environments for MCS development. During summer, the composite MCS environment shows small positive convective available potential energy (CAPE) and convective inhibition (CIN) anomalies, which are in stark contrast with the large positive CAPE and negative CIN anomalies in spring. This contrast suggests that summer convection may occur even with weak large-scale dynamical and thermodynamic perturbations so MCSs may be inherently less predictable in summer. The two synoptically favorable environments identified in summer have frontal characteristics and an enhanced GPLLJ, but both shift north compared to spring. The two synoptically unfavorable environments feature enhanced upper-level ridges, but differ in the strength of the GPLLJ. In both seasons, MCS precipitation amount, area, and rate are much larger in the frontal-related MCSs than in nonfrontal MCSs. A large-scale index constructed using pattern correlation between large-scale environments and the synoptically favorable SOM types is found to be skillful for estimating MCS number, precipitation rate, and area in spring, but its explanatory power decreases significantly in summer. The low predictability of summer MCSs deserves further investigation in the future.