Public concern on the methods of raising food-producing animals has increased, especially in the last two decades, leading to voluntary and mandated changes in the animal production methods. The primary objective of these changes is to improve the welfare of farm animals. The use of gestational stalls is currently a major welfare issue in swine production. Several studies assessed the welfare of alternative housing systems for gestating sows. A comparative study was performed with gestating sows housed in either individual stalls or in groups in a pen with an electronic sow feeder. This review assessed the welfare of each housing system using physiological, behavioral, and reproductive performance criteria. The current review identified clear advantages and disadvantages of each housing system. Individual stall housing allowed each sow to be given an individually tailored diet without competition, but the sows had behavioral restrictions and showed stereotypical behaviors (e.g., bar biting, nosing, palate grinding, etc.). Group-housed sows had increased opportunities to display such behavior (e.g., ability to move around and social interactions); however, a higher prevalence of aggressive behavior, especially first mixing in static group type, caused a negative impact on longevity (more body lesions, scratch and bite injuries, and lameness, especially in subordinate sows). Conclusively, a more segmented and diversified welfare assessment could be beneficial for a precise evaluation of each housing system for sows. Further efforts should be made to reduce aggression-driven injuries and design housing systems (feeding regimen, floor, bedding, etc.) to improve the welfare of group-housed sows.