Chickering has received numerous awards for his service to the development of the fields of student affairs and college student development theories. These include:
- the E.F. Lindquist Award from the American Educational Research Association for his studies of college impacts on student development
- the Outstanding Service Award from the National Association of Student Personnel Administrators
- the Distinguished Contribution to Knowledge Award from the American College Personnel Association
- the Distinguished Service Award from the Council for Independent Colleges
- the Howard R. Bowen Distinguished Career Award for the Association for the Study of Higher Education, for extraordinary contributions to research, leadership and service.