Chicago Transit Authority has a Military Service Pass for current servicemembers and disabled veterans.

Cook Country Discount Card Program allows all Cook County Veterans, active-duty personnel, national guard, reservists, and other members of the military to apply for the free Military and Veterans Discount Program. The card provides veterans with discounts on a wide range of services at businesses including home improvement, dining, auto repair, health and fitness, and more. 

GovX is a website that provides exclusive discounts for current and former military, first responders, and law enforcement.

Military and Veteran Discounts has a list of a large number of companies that provide veterans discounts. You will be asked to register and provide proof of service.

Vet Tix provides free tickets to veterans. The tickets are given freely, or in some cases, raffles and lotteries are held. You will be asked to register and provide proof of service.