Urban environments impose novel challenges on animals and, as a result, the behaviors of urban wildlife are changing. In particular, high exploratory tendencies and an ability to gather more information from the environment may facilitate adoption of novel ecological opportunities. As of yet, very few studies have examined if urbanization predicts the way in which animals explore novel environments, or the extent of among-individual variation within habitats. Here, we assess exploration and it’s temporal plasticity in black-capped chickadees (Poecile atricapillus; N=169 individuals, 14 sites) caught along an urban gradient to examine individual differences in exploration and changes in exploration over time and assays under a reaction-norm framework. As predicted, urban birds were significantly faster explorers in a novel environment (contacted more features and moved more), however urbanization did not predict individual differences in the change in exploration over time. Exploration score was moderately repeatable; interestingly, urban chickadees were more repeatable in their initial exploration behaviors, but seemed less repeatable in how they explored over time between assays in comparison to forest birds. Our results support the importance of high exploratory tendencies for urban animals, and suggest, for the first time, that individuals from urban and non-urban habitats differ in the amount of among-individual variation in exploration, and thus urban individuals may benefit from diverging more from one another in their behaviour. Future work should examine the extent to which this variation in exploration and plasticity of exploration behaviors represent differences in how individuals gather information from their environment.