Crop species are known to hybridize spontaneously with wild relatives, but few studies have characterized the performance of hybrids at various genealogies, life stages and environments. A group of cultivar-like individuals and potential hybrids were observed in a roadside population of wild chicory plants in Denmark. Seeds were collected from all reproductive plants and grown in a common garden experiment, and their morphological and genetic compositions were analysed. Intermediate plants were identified as hybrids and comprised various backcross and F(n) combinations. A genotypic hybrid index (HI), spanning from wild-like to cultivar-like, was highly correlated to a morphological index. Plant survival, growth and reproduction were evaluated and compared to the genotypic HI. Overall, cultivar-like and intermediate plants grew larger than wild-like plants, flowered longer, and produced more flowers and seeds. The common garden included a nutrient gradient. At higher nutrient levels, intermediate and cultivar-like plants produced more flowers and seeds than wild-like plants, whereas this effect was less pronounced at lower nutrient levels. During winter, small rodents consumed roots of cultivar-like and intermediate plants preferentially. Thus, cultivated and wild chicory are able to hybridize spontaneously, producing hybrid offspring of several generations that may reproduce more effectively than their wild parent, but herbivory and poor environmental conditions may negatively affect their fitness.