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The social integration of a city depends on the extent to which people from different neighborhoods have the opportunity to interact with one another, but most prior work has not developed formal ways of conceptualizing and measuring this kind of connectedness. In this article, we develop original, network-based measures of what we call “structural connectedness” based on the everyday travel of people across neighborhoods. Our principal index captures the extent to which residents in each neighborhood of a city travel to all other neighborhoods in equal proportion. Our secondary index captures the extent to which travels within a city are concentrated in a handful of receiving neighborhoods. We illustrate the value of our indices for the 50 largest American cities based on hundreds of millions of geotagged tweets over 18 months. We uncover important features of major American cities, including the extent to which their connectedness depends on a few neighborhood hubs, and the fact that in several cities, contact between some neighborhoods is all but nonexistent. We also show that cities with greater population densities, more cosmopolitanism, and less racial segregation have higher levels of structural connectedness. Our indices can be applied to data at any spatial scale, and our measures pave the way for more powerful and precise analyses of structural connectedness and its effects across a broad array of social phenomena.