Startup Grind Chicago is the city's longest-standing startup community hosting monthly events.

Startup Grind Chicago serves as the city's longest-standing startup community and a gateway to the world's largest startup network, which spans over 125 countries and 600 cities. Hosted by Rajiv 'RajNATION' Nathan and Sid Khaitan, the group operates on three core values: Give First, Make Friends, and Help Others. Their mission is to provide startups everywhere with the education and opportunities they need to build, grow, and scale their companies. The chapter hosts monthly events designed to connect, inspire, and educate the Chicago ecosystem, offering resources such as a 'Works in Progress' clinic where founders share their challenges and receive real feedback. Members gain access to a newsletter, networking events, mentorship, office hours, and exclusive tools and discounts curated by Startup Grind HQ. The group celebrates local success, such as the 2025/'26 Chicago Rising Startup of the Year, Collars, and encourages participation in their global initiatives, including the annual Startup Grind Conference in Silicon Valley. Joining the chapter is free, allowing members to stay updated on perks, announcements, and upcoming gatherings.