ChooseHealthDE.com is the free Official State Program & website to help you understand health insurance reform and the Health Insurance Marketplace. Key Dates: 11/1/2016, Enrollment Begins 12/15/2016, Last day to enroll for coverage starting January 1, 2017 1/15/2017 Last day to enroll for coverage starting February 1, 2017 1/31/2017, End of Enrollment It’s important to remember that after open enrollment ends on February 15, 2015, you won’t be able to get health coverage through the Enrollment for Medicaid, CHIP and Special Enrollment can occur at any time of the year.