Positive associations between measures of school or academic connectedness and behavioral and academic outcomes suggest that connectedness is an important protective factor for adolescents in the United States. However, little is known about the meaning or measurement of academic connectedness, outside the United States, and especially in South America where rapid economic and educational changes are underway. Using the Hemingway: Measure of Adolescent Connectedness measurement invariance analyses were conducted that compared Chilean and United States samples. Results revealed that although all scales reflected factorial validity in both cultures, the connectedness to school, teachers, and self-in-the-future factors were noninvariant across groups, whereas the factors of connectedness to peers and self-in-the-present were invariant across groups. Consequently, all of these subscales can be used in both contexts, but comparing United States and Chilean youth on three subscales may be ill advised. (Contains 1 figure and 4 tables.)