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Square Cornerstone Grant
Applications Open Until September 30, 2025
Awardees will receive a $10,000 grant along with financial guidance through a year of CPA mentorship and features in the Square newsletters. Apply here.
Eligibility:
- Current Square seller, with at least 6 months of ongoing transactions
- US based business with fewer than 20 employees
- Must qualify as a small business under SBA guidance and have a gross annual revenue under $2M
- Applicants must be legal US residents and their business must not currently be in bankruptcy or named as a defendant in an active lawsuit
Interested businesses must apply online and will receive determinations in November. Learn more and apply now.
Community Development Grants - Small and Medium
Applications Open Until 11:59PM February 13, 2026.
Receive up to $250,000 (small) or $5 million (medium) for construction or renovation costs for your business. Grants support local commercial and light manufacturing projects. Apply here.
Eligibility:
- Proposed projects must be revenue-generating
- Projects must comprise the following uses
- Commercial (office, retail)
- Light industrial
- Mixed-use residential (residential costs cannot exceed 25% of the total grant amount and must be part of a larger building improvement, such as HVAC/plumbing)
- Priority is given to projects with strong local impacts that leverage local talents, capacities and institutions and contribute to community vitality.
Additional Information:
Note that this is a reimbursement grant. Eligible costs include pre-development, new construction and renovations. Applications are open to business owners, property owners, community developers, and entrepreneurs. Apply now.
City of Chicago Workforce Solutions Grant
Applications Open On A Rolling Basis
The Workforce Solutions program is a reimbursable training grant initiative provided by the City of Chicago's Department of Planning and Development designed to support Chicago employers seeking to enhance the skills of their existing workforce and/or onboard new employees through targeted training initiatives. Reimbursement grants cover up to 100% of total eligible project costs up to a standard maximum award of $250,000. Note that at this time funding is only still available for applicants located within eligible TIF districts. Apply here.
Eligibility:
- A company, organization, or nonprofit located in, expanding into or relocating to the City of Chicago
- An active non-profit organization, such as an industrial council, community development corporation, business/trade association or labor organization
- A company, organization or nonprofit planning to remain operational in their community area for a term no less than three years
- A financially sound business/organization not solely dependent on Workforce Solutions grants to stay in business
Eligible Costs:
- Market expansion training
- Staff development
- Company- or job-specific skills-based training
- Industry-required trainings
Additional Information:
Note that citywide applications are expected to reopen in Q1 2026. At this time, projects within eligible TIF districts can still apply. Apply now.
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