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Originally designed by Donald Ross on 110 acres in 1916, the course was rebuilt in 1924 after the purchase of the 50 additional acres of land west of the Skokie River. Captain Charles Hugh Alison of the English firm of Colt, McKenzie and Alison redesigned the course to utilize this additional land. Though renovated at times, the Alison design has served as the foundation of the course since reopening on July 4th 1925.

The course at Bob O’Link is one of only 33 Colt & Alison golf courses remaining in North America.

In 2015, the members of Bob O’Link invested significantly in the preservation of the historic, Alison designed course, courageously passing the Centennial Initiative. This was the largest undertaking at the Club since Alison redesigned the Ross course in 1924.

The project, led by famed architect, Jim Urbina included restoration of 60 original Alison bunkers, recapturing acres of lost fairway space, removal of trees that had suffocated turf, rebuilding of all greens to USGA specifications while maintaining the historic Alison shapes and contours, a new, state of the art irrigation and drainage pump system, and regrassing all playing surfaces. The course re-opened in June of 2016 and is now one of the best representations of C. H. Alison's work in the US.