Total Retiree Advantage Illinois (TRAIL) Program

The 2026 TRAIL 
Medicare Advantage Prescription Drug (MAPD)
Open Enrollment Period
will run
October 14 – November 14, 2025

To view the dates and locations of the 2026 TRAIL in-person seminars, click here.

The State of Illinois offers retirees, annuitants, and survivors (of the State Employees Group Insurance Program (SEGIP), The Teachers' Retirement Insurance Program (TRIP), and the College Insurance Program (CIP)) a healthcare program entitled Total Retiree Advantage Illinois (TRAIL). This program provides Medicare-eligible members and their covered dependents comprehensive medical and prescription drug coverage through TRAIL Medicare Advantage Prescription Drug (commonly referred to as "MAPD") plans.

For members who are newly eligible for Medicare, you will have two opportunities for enrollment:

Initial Enrollment (IE): this is offered to all Medicare-eligible retirees and their Medicare-eligible dependents within 60-days of the 65th birthday (of the youngest enrollee). Initial enrollment is a one-time offering.

To better prepare for your Medicare Enrollment, click here to review this Medicare Checklist:

• Medicare Checklist for State Retirees
  
• Medicare Checklist for Active State Employees
• Medicare Checklist for CIP Retirees
  
• Medicare Checklist for TRIP Retirees

Open Enrollment (OE): an annual enrollment period held in the fall of each year. This enrollment period is open for Medicare-eligible retirees, survivors, and their dependents to change their elections, or for anyone who previously waived or canceled coverage to re-enroll.

Review the eligibility criteria and an explanation of the benefits provided through the Program.

During both opportunities for enrollment (IE & OE), retirees and survivors eligible for the TRAIL MAPD Program will receive an Enrollment Guide in the mail, notifying them of their eligibility and the requirement to enroll or waive coverage, during the TRAIL MAPD Open Enrollment Period. 

Note: Members who are currently enrolled in TRAIL MAPD, you do not need to do anything during the Open Enrollment Period, unless you want to add/drop a dependent, opt-out of coverage, or make changes to other coverages (if applicable). In order to make changes for the 2026 plan you, you will need to either complete your changes online at MyBenefits.illinois.gov or contact the MyBenefits service center (toll-free) 844-251-1777 during the Open Enrollment Period. No elections are allowed to be made prior to October 14^th , or after November 14^th.

This program provides medical, prescription, vision, and dental insurance benefits for annuitants receiving a monthly benefit or annuity from the State Universities Retirement System (SURS) who prior to retiring, were an employee of an Illinois community college.

This program provides medical, prescription, vision, dental, and life insurance benefits for certain former elected state officials and the employees under their jurisdiction, as well as retirees, annuitants, and survivors of prior employees of state agencies, boards, commissions, and universities.

This program provides medical, prescription, vision, and dental insurance benefits for annuitants receiving a monthly benefit or annuity from the Teachers’ Retirement System (TRS) who prior to retiring, were an employee of an Illinois school district.