15 Entrepreneurship Summer Programs in Chicago for High School Students

By participating in finance summer programs in Chicago, you'll see how financial systems actually work, how businesses make strategic decisions, and how entrepreneurs transform ideas into successful ventures. 

What do entrepreneurship summer programs look like?

Entrepreneurship summer programs in Chicago typically combine academic learning with real-world application. You might study topics such as financial markets, investing strategies, corporate finance, and entrepreneurship, and then apply what you learn through projects and case studies.

Why participate in entrepreneurship summer programs in Chicago?

These programs are useful because they help students connect theoretical knowledge with practical application. Instead of simply learning financial terms, you'll work through real-world scenarios that demonstrate how financial decisions impact businesses and economies. This practical experience can help you figure out what interests you most, whether it’s investment analysis, corporate strategy, or entrepreneurship, before you commit to a college major or career path.

For related opportunities, consider business internships in Chicago.

Quick Look

• 4 free or paid programs: CSBI (paid stipend, Chicago residents with household income under $80k), Genesys Works (students earn $10,000-$13,000 across training and internship), Future Founders Be Your Own Boss (paid stipend), and DePaul Invest for Kids (free, covered in the Finance Workshops blog)

• 3 fully virtual programs open to students outside Chicago: Young Founders Lab, Ladder Internship, and UChicago Summer Online — all available year-round with financial aid

• 5 programs restricted to Chicago residents or CPS students: CSBI, CPS-UChicago Dual Enrollment, Genesys Works, Future Founders, and SparkShop

• 3 programs where you earn college credit: Northwestern Financial Accounting (3 quarter credits), CPS-UChicago Dual Enrollment (recorded on CPS transcript, equivalent to AP weighting), and UChicago Summer Online (academic credit from UChicago on completion)

• 2 programs open to 8th graders or rising 9th graders: UChicago Pathways in Economics (grades 9-11) and UChicago Career Insight Business and Entrepreneurship (grades 9-11, ages 14+)

• Earliest deadlines: SparkShop (January), Northwestern Financial Accounting (March 16), CSBI (March 31), UChicago Career Insight (priority February, regular March)

​15 Entrepreneurship Summer Programs in Chicago for High School Students

1. Chicago Summer Business Institute (CSBI)

Location: Chicago, IL

Cost: Paid internship (stipend provided)

Application Deadline: March 31

Dates: June – July (6 weeks)

Eligibility: You must be a Chicago resident, a high school sophomore or junior, maintain at least a 3.0 GPA, come from a household earning under $80,000 annually, and be able to commit to the program’s daily schedule

CSBI is a six-week, full-time summer internship program in Chicago for high school students interested in gaining workplace experience. During the program, you'll be placed with an organization such as a financial institution, corporate office, nonprofit organization, or city agency, whereyou contribute to day-to-day operations.

Your responsibilities may include working with spreadsheets, assisting with basic accounting records, preparing documents, conducting internal research, or helping with administrative and operational tasks. Alongside the internship, you participate in professional development workshops focused on building essential career skills. These sessions typically cover topics such as resume writing, interview preparation, workplace communication, and time management.

2. Young Founders Lab

Location: This program is 100% virtual, with live, interactive workshops

Cost: Varies depending on program type. Full financial aid available

Application Deadline: Varies according to cohort. You can access the application link here!

Dates: Multiple cohorts throughout the year, including summer, fall, winter, and spring

Eligibility: The program is currently open to all high school students

The Young Founder’s Lab is a start-up-focused program created by entrepreneurs associated with Harvard. During the program, you work on developing a start-up idea aimed at solving a real-world problem with the goal of building a model that could generate revenue. Throughout the program, you receive guidance from entrepreneurs and industry professionals, including individuals who have worked at companies such as Google, Microsoft, and X.

Besides working on your venture, you participate in sessions covering business fundamentals and idea development. The program also includes workshops, case studies, panel discussions, and other interactive activities that will introduce you to different approaches to building and managing a business. Through these experiences, you explore both theory and practical strategies related to entrepreneurship while still in high school.

3. University of Chicago Pathways in Economics

Location: University of Chicago, Chicago, IL

Cost/Stipend: $9,300 (residential; need-based financial aid available)

Application Deadline: Unspecified (requires transcript, essays, recommendation, writing sample, parent confirmation, and fee)

Dates: Session 1: June 15 – July 2

Eligibility: High school students grades 9–11, pre-calculus prerequisite, strong interest in math/economics

The University of Chicago’s Pathways in Economics program introduces high school students to how economists think, analyze problems and study real-world issues. During the program, you attend lectures led by faculty from the economics department covering areas such as macroeconomics, microeconomics, game theory, and experimental research methods. As part of the program, you'll examine topics such as economic growth, patterns of consumption and saving, business cycles, and the impact of fiscal and monetary policy. 

While the program primarily focuses on economics, it also connects naturally to broader interests in business and entrepreneurship. The university offers related learning opportunities, such as Career Insight: Business and Entrepreneurship at University of Chicago.

4. Ladder Internship Program

Location: Remote! You can work from anywhere in the world

Cost: Full financial aid available

Application Deadline: Deadlines vary depending on the cohort

Dates: Multiple cohorts throughout the year

Eligibility: Students who can work for 10–20 hours/week, for 8–12 weeks. Open to high school students, undergraduates, and gap year students!

Ladder Internships offers a start-up internship experience designed for high school students interested in gaining practical work exposure while still at school. During the program, you are placed with a start-up company and work on projects related to its ongoing operations. The start-ups you may work with span a range of fields, including technology, artificial intelligence and machine learning, health technology, marketing, journalism, and consulting. Many of the companies participating in the program are early-stage or growing start-ups that have secured funding to support their development. 

Some founders have previous experience working at large technology companies or have been involved in startup accelerator programs. As an intern, you collaborate with a manager at the start-up and receive guidance from a Ladder Coach throughout the program. You contribute to project-based work connected to the company’s activities and conclude the experience by presenting your work and key takeaways to the team. This experience allows you to observe how start-ups function, while building practical skills in problem-solving, teamwork, and professional communication.

5. University of Chicago Summer Online

Location: Online

Cost: 3–5 Week Summer Online: $4,980. Need-based financial aid is available

Application Deadline: Priority: February 11; Regular: March 12

Dates: June – August (varies by course)

Eligibility: You must be in grades 9–11 for pre-college–designed courses, or grades 11–12 for select undergraduate College courses. Course-specific prerequisites may apply

This program gives you the opportunity to take an online course taught by instructors from the University of Chicago. Classes include scheduled live sessions, guided discussions, and collaborative assignments with other students. Some courses are designed specifically for high school participants, while others allow you to study alongside undergraduate students and complete the same graded coursework. 

Depending on the course you choose, you might explore topics such as economics, behavioral decision-making, or data analysis. During the program, you follow a structured academic schedule that includes assigned readings, written assignments, and assessments. Upon successful completion of the course, you'll earn academic credit from the University of Chicago.

6. CPS–UChicago Summer Scholarship Program (Dual-Enrollment Pathway)

Location: Chicago, IL (University of Chicago campus)

Cost: $800 tuition for households earning under $125,000; Free for students from households earning under $60,000

Application Deadline: Mid – July (application opens mid-May)

Dates: Year-round academic program with summer course options available; course dates vary by department

Eligibility: You must be a Chicago Public Schools student, entering junior or senior year, with a strong academic record in a college-preparatory curriculum. You must also demonstrate readiness for undergraduate-level coursework. Recommendation letters and an interview are required

This program gives you the opportunity to take an undergraduate course at the University of Chicago and earn academic credit while still in high school. You'll attend classes alongside university students and complete the same readings, assignments, and examinations, giving you an authentic college classroom experience. If you are interested in business-related subjects, you can find relevant courses through economics or other social science departments. 

The coursework follows a college-level pace and requires consistent engagement with readings, written assignments, and assessments. After completing the course, it is recorded on your CPS transcript and carries the same weightage as an Advanced Placement course.

7. Northwestern College Preparation Program — Introduction to Financial Accounting

Location: Online (Northwestern School of Professional Studies College Prep)

Cost: $5,781/class (3 quarter credits)

Application Deadline: March 16

Dates: June 22 – August 30 (3 – 10 weeks, asynchronous)

Eligibility: High school sophomores/juniors (College Credit), cumulative GPA 3.0, personal statement, extracurriculars, transcripts

The College Preparation Program at Northwestern University offers ACCOUNT 201-DL: Introduction to Financial Accounting for high school sophomores and juniors interested in learning how businesses manage their finances. In this course, you study how financial information is identified, recorded, and communicated to external users using  generally accepted accounting principles (GAAP).

The course is delivered online in an asynchronous format, allowing you to manage your own schedule while keeping up with lectures and assignments. By the end of the program, you'll develop skills related to financial reporting, budgeting, and analyzing financial information, which can be useful for understanding how businesses and startups manage their finances. 

8. Junior Economic Club of Chicago — Careers in Business (CIB) Internship Program

Location: Chicago, IL (hybrid or in-person depending on placement)

Cost: No program fee; compensation varies by internship (paid status depends on partner organization)

Application Deadline: Rolling (subject to internship availability)

Dates: Summer (exact dates vary by internship placement)

Eligibility: You must be a high-performing high school student and a member or applicant of the Junior Economic Club of Chicago. Selection is competitive and based on interest, readiness, and fit with partner organizations

The CIB Internship Program gives you the opportunity to work with an organization partnered with JEC, such as a startup, financial services firm, or investment-related company. During the internship, you may assist with activities such as company research, market analysis, or supporting projects related to investment evaluation, underwriting, marketing, or business development. 

Some placements take place in early-stage startup environments, while others involve firms focused on finance, strategy, or advisory work. In each case, you'll work with professionals at the host organization and contribute to ongoing tasks or projects rather than simulated assignments. 

9. DePaul University — Invest for Kids Summer Investment Challenge

Location: DePaul University Lincoln Park and Loop campuses, Chicago, IL

Cost: Free

Application Deadline: Not publicly specified

Dates: Five days in the summer (exact dates vary)

Eligibility: You must be a high school student interested in finance or investing. Selection is competitive and based on interest and readiness for college-level material

The Invest for Kids Summer Investment Challenge at DePaul University is a short finance program that introduces high school students to the basics of valuation and investment analysis. During the program, you work as part of a sponsored team while following a structured set of lessons on topics such as financial markets, asset pricing, and how investment decisions are made.

A key part of the experience is hands-on learning; you'll use  practical tools commonly used in finance, such as building models in Excel, working with Bloomberg terminals, and examining real market data. You'll also attend seminars and site visits led by professionals from the financial industry, gaining insights into how finance works beyond the classroom.

10. University of Chicago — Career Insight: Business and Entrepreneurship

Location: University of Chicago campus; Chicago, IL

Cost: $5,890; need-based financial aid is available

Application Deadline: Priority and regular deadlines vary by cycle

Dates: June 15 – 25

Eligibility: You must be a high school student in grades 9–11. Admission requires a transcript, essays, a recommendation letter, and a writing sample

The Career Insight program at University of Chicago blends classroom learning with practical exposure to business careers. In the mornings, you participate in lectures, readings, and discussions led by faculty on topics such as entrepreneurship, finance, leadership, and economics.

Afternoons are dedicated to applied activities, including visits to companies, informational interviews, and sessions with business professionals. You'll also collaborate in small groups on projects that connect the concepts you study in class with real-world organizational roles. Throughout the program, written reflections help you think critically about your experiences and how effectively you can link theoretical ideas to real business situations.

11. University of Illinois Chicago — Future Business Tech Leaders

Location: Chicago, IL (University of Illinois Chicago campus)

Cost: Not specified (meals provided)

Application Deadline: June 1

Dates: One-day program in late June

Eligibility: You must be entering your sophomore, junior, or senior year of high school, have a minimum 3.0 GPA, demonstrate interest in business or related fields, and express interest in attending UIC

The Future Business Tech Leaders program at the University of Illinois Chicago is a one-day, on-campus introduction to careers in business and technology. Through interactive workshops, you'll explore how technology is used to support various business functions.

During the program, you'll learn about a range of business-related fields, digital tools, and emerging career opportunities. Faculty and staff also lead discussions on preparing academically and understanding professional expectations. The program is intended as an introductory experience to give you an overview of business and technology careers rather than in-depth training.

12. Genesys Works — Young Professionals Program

Location: Chicago, IL (training + corporate internship sites)

Cost: Paid program (students earn approximately $10,000 – $13,000 over training and internship)

Application Deadline: Applications typically open in fall or winter (dates vary by cohort)

Dates: Summer: 8 weeks of skills training; Academic Year: Part-time paid internship during senior year

Eligibility: You must be a high school junior on track to graduate, authorized to work in the U.S., and able to adjust your senior-year course schedule to accommodate a 20-hour-per-week internship

The Young Professionals Program through Genesys Works is a multi-step workforce development experience that combines training with paid work. You start with an eight-week summer program that covers professional communication, workplace technology, project management, and basic business principles.

After completing the summer training, you transition into a part-time, paid internship during your senior year. In this role, you'll contribute to ongoing projects and support day-to-day operations within a corporate team. Throughout the program, you'll receive guidance on college planning, financial aid, and career decisions. The program is structured to help you develop reliability, workplace skills, and an understanding of how organizations function from the inside.

13. Future Founders — Be Your Own Boss Internship

Location: Virtual (Chicago-based organization; occasional in-person events in Chicago)

Cost: Paid internship (cash stipend based on attendance and participation)

Application Deadline: Varies by the cohort

Dates: Various cycles throughout the year

Eligibility: You must be a high school student enrolled in a public or charter school. The program prioritizes students from low-income and urban or rural settings. No prior entrepreneurship experience is required; admission includes an application and virtual interview

The Be Your Own Boss Internship through Future Founders is a short-term, paid virtual program that introduces you to the basics of building a startup. You'll work in a team to develop a business concept, starting from identifying a problem and working toward preparing a final pitch.

Along the way, you'll take part in activities such as analyzing customer needs, creating a simple app prototype, and refining a value proposition. Founders and business professionals lead sessions and provide feedback on your progress. By the end of the program, you'll have a clear understanding of how businesses are built from the ground up.

14. AGB Foundation — Summer Business Internship

Location: Chicago, IL (various minority-owned or minority-operated businesses, nonprofits, and public organizations)

Cost: Paid internship

Application Deadline: April – May

Dates: Summer (six weeks; exact dates vary by year)

Eligibility: You must be a high school student (including college-age young adults). While the program prioritizes students from minority backgrounds and first-generation families, all motivated, high-performing students are encouraged to apply

The Summer Business Internship through the AGB Foundation places you in a six-week, paid position at a business, nonprofit, or public organization in the Chicago area. You'll work part-time under the guidance of a mentor and rotate through different departments, gaining exposure to areas such as accounting, human resources, sales, and marketing.

Your responsibilities may include shadowing professionals, attending meetings, and contributing to assigned projects. Besides daily work tasks, the program provides opportunities to develop skills in professional communication, business correspondence, teamwork, negotiation, and networking.

15. SparkShop — High School Summer Internship Program

Location: SparkShop HQ and partner community sites, Chicago, IL

Cost: Paid internship

Application Deadline: January (check website for exact date)

Dates: Two weeks in July

Eligibility: You must be a Chicago-based high school student (any grade level), be at least 16 years old, and demonstrate curiosity and motivation. No prior STEM or business experience is required; the program welcomes students from all backgrounds and skill levels

The High School Summer Internship at SparkShop is a two-week, paid program that gives you hands-on experience working on real projects. Depending on your placement, you may work on short-term projects related to business operations, marketing, community outreach, or internal planning.

The program helps you build skills such as project management, teamwork, presentations, and professional communication through practical tasks rather than classroom lessons. You'll collaborate with SparkShop staff and other interns, gaining insights into how a growing organization coordinates work across different functions. Mentors provide ongoing guidance and feedback throughout the program, helping you improve and reflect on your work.

Frequently Asked Questions

1. Are there free entrepreneurship summer programs for high school students in Chicago? Yes, several programs are free or provide a stipend. CSBI places Chicago-area high school sophomores and juniors with organizations and pays a stipend, with an income eligibility requirement. Genesys Works is the most financially rewarding program on this list, with students earning approximately $10,000-$13,000 across an 8-week summer training and a year-long paid internship, and is primarily designed for first-generation college students. Future Founders Be Your Own Boss pays a cash stipend for full participation and is open to Chicago Public Schools and charter school students. DePaul's Invest for Kids finance challenge is also free for Chicago-area students interested in investing and financial markets specifically.

2. Which Chicago entrepreneurship programs are available to students outside the city? Most in-person programs on this list are restricted to Chicago residents or CPS students. The 3 programs with no location requirement are Young Founders Lab (100% virtual, all high school students, financial aid available, multiple cohorts throughout the year), Ladder Internship (fully remote, places students with real startups, multiple cohorts year-round), and UChicago Summer Online (online courses taught by UChicago faculty, open to grades 9-11 or 11-12 depending on the course, financial aid available). All three are also accessible to Chicago students who prefer a remote format.

3. Which programs are best for students who want real startup or work experience rather than classroom learning? Four programs stand out for hands-on work experience. Young Founders Lab has you building a real, revenue-generating startup from the ground up with mentorship from entrepreneurs and professionals from Google, Microsoft, and YC-backed companies. Ladder Internship places you with an actual high-growth startup where you work on real projects and present deliverables to the company. CSBI places you at a financial institution, corporate office, or nonprofit where you contribute to day-to-day operations. Genesys Works pairs 8 weeks of skills training with a paid year-long corporate internship during senior year, making it the most immersive work experience on this list.