At the North Shore, Kamehameha Highway heads northeast around the northern tip of O‘ahu, then southeast to and just beyond Kāne‘ohe Bay on the windward coast.

This segment runs as a short extension of Dillingham Boulevard from Pu‘uhale Road (near the O‘ahu Community Correctional Center) to exit 18B on Interstate H-1.

The highway then turns west through the suburbs of ‘Aiea and Pearl City, passing Pearlridge Center, the state's second largest shopping mall.

After passing Pearl City and the interchange with Interstate H-2 near Waipahu, Route 99 turns north through the central O‘ahu suburbs of Waipi‘o and Mililani.

It then continues southward along the shore of the Kāne‘ohe Bay, until its southern terminus with Routes 63 and 83, only 1.5 miles away from Interstate H-3.