Is Chicago a Good Place to Launch a Startup?

Where you start your company still matters – but sticking too closely to one location might limit what you’re able to build. In today’s startup landscape, geography shapes your path – but it doesn’t have to define your potential.

Chicago has emerged as a strong hub for entrepreneurship, offering access to funding, talent, and infrastructure. But with growing competition, rigid local programmes, and support often reserved for the most polished startups, relying solely on what’s nearby can slow you down – or hold you back.

In this article, we’ll explore what Chicago gets right – and where founders often run into friction. We’ll also show how EWOR offers an alternative: a global, remote-first platform that gives you access to funding, mentorship, and community – no matter where you’re based.

1. Access to Funding in Chicago

Funding is one of the most critical ingredients in building a successful startup – and Chicago offers a growing ecosystem of support. From venture capital firms to government grants and angel investors, founders in this region have several pathways to raise capital and gain early traction.

Chicago's early-stage funding scene is supported by active players like M25, Hyde Park Venture Partners, and OCA Ventures, alongside angel networks such as Hyde Park Angels and Chicago Booth Angels Network. Government initiatives like the City of Chicago's Small Business Improvement Fund (SBIF) and the Neighborhood Opportunity Fund (NOF) also offer grants for building improvements. Despite these resources, challenges persist. While total funding saw a slight increase in 2024, the number of deals decreased significantly from its peak in 2021, reflecting a national trend of slower investment activity. Some reports also indicate that securing early-stage funding can still be difficult, and there's a notable gap in access to capital for businesses owned by people of color. Additionally, startups that raise larger funding rounds are more likely to leave the state.

A More Flexible Path Forward

In the wake of these challenges, founders don’t have to rely solely on local funding options. EWOR offers a more flexible path – providing up to €500,000 in early-stage capital But EWOR is more than a cheque. Our capital comes bundled with personalised support, investor-ready storytelling, and access to a network of over 400 active European investors – many of whom regularly participate in our Grand Pitch events. On average, EWOR fellows who complete the programme and pitch go on to raise €2 million in follow-on funding – over 10x more than founders from comparable European initiatives.

2. Innovation and Startup Culture  

Chicago has become a centre of innovation, with numerous tech hubs, coworking spaces, and accelerators that foster creativity and new ideas. The local startup culture is vibrant, with a growing community of entrepreneurs working together to push the boundaries of what’s possible.

Chicago has a thriving startup and innovation ecosystem with numerous coworking spaces and frequent tech and entrepreneurial events. There is significant entrepreneurial activity across diverse sectors like tech, fintech, and healthcare. The ecosystem offers support for early-stage founders through various accelerators, incubators, and university programs, some providing tailored mentorship and resources. While standardized programs exist, there are also initiatives and investors focused on supporting early-stage companies and underrepresented founders with personalized guidance.

For many entrepreneurs, the energy and resources available in Chicago can provide the ideal environment to test new ideas and gain early traction. The collaborative atmosphere allows founders to connect with fellow innovators and build networks that can help their startups grow.

While the local startup culture is vibrant, the support founders actually receive can be hit or miss. VCs might offer funding but little time. Angel investors often give advice, but it’s scattered and inconsistent. What’s more, many accelerators rely on a one-size-fits-all model that doesn’t reflect the needs of exceptional founders. In fast-moving, competitive ecosystems like Chicago, standing out is hard enough – getting the right kind of support shouldn’t be.

The Alternative to Cookie-Cutter Programmes

Finding a programme that truly adapts to your journey, not the other way around, is rare. However, EWOR offers the kind of depth and flexibility that many local programmes simply can’t match. Instead of following a fixed curriculum, our fellowships are modular and tailored – giving you the right support at the right time, based on where you are in your journey.

But the real strength of EWOR goes beyond structure. Fellows often describe the community as the most unexpected – and valuable – part of the experience. As some have put it: “The real magic lies in the community: the kind of conversations, insights, and connections that lead not only to breakthroughs – but to lasting friendships with some of the most fascinating people they’ve ever met”.

3. Talent and Workforce Availability

One of the greatest assets of launching a startup in Chicago is access to a skilled and diverse talent pool. With universities producing top-tier graduates in technology, business, and other fields, startups can tap into a wealth of expertise to help grow their teams.

Chicago has a diverse and abundant talent pool for startups, fueled by numerous top universities like the University of Chicago, Northwestern University, and the University of Illinois. These institutions produce skilled professionals in technology, healthcare, finance, and marketing, with strong programs in STEM and entrepreneurship. Chicago's talent is particularly strong in areas like technology, healthcare, fintech, and manufacturing. Local talent supports entrepreneurial growth through participation in university entrepreneurship programs, accelerators like 1871 and Techstars, and by possessing in-demand skills such as programming, AI/machine learning, cybersecurity, and data engineering.

Like funding, competition for talent can be fierce, especially for highly specialised roles in fields like software development or AI. For startups looking to scale quickly, hiring the right people at the right time can be a challenge, leading some founders to look outside the region for remote talent solutions.

Get Global While Local

While hiring locally in Chicago can be competitive and slow, EWOR gives you instant access to a global network of exceptional talent. Built by founders for founders, the EWOR team has launched and exited companies worth over €12 billion – and they bring that experience directly into your venture. It's not just about funding or surface-level advice; it's akin to having a co-founder from day one. 

The team collaborates closely with you to refine your idea, challenge your thinking, and support you through real-world decisions – just like a hands-on partner would. Moreover, with EWOR’s exclusive co-founder pool, you can find the right person to build with, regardless of their location.

4. Infrastructure and Support Systems

Chicago boasts a strong infrastructure that supports the growth of new businesses. From modern office spaces to high-speed internet, entrepreneurs have access to everything they need to run their startups smoothly. Government policies may also provide tax breaks, legal support, and other incentives that make starting a business more attractive in this region.

Chicago offers a robust ecosystem for startups, featuring numerous incubators and accelerators like 1871, Techstars Chicago, and the Polsky Center at the University of Chicago, providing mentorship, resources, and funding opportunities. Co-working spaces and a strong venture capital presence, including firms like Chicago Ventures and Hyde Park Venture Partners, facilitate access to funding and networking. These resources help businesses thrive by offering crucial support in areas like product development, market strategy, and fundraising. The city's central location and transportation infrastructure also aid connectivity. Government initiatives, such as those from the Illinois Department of Commerce & Economic Opportunity and the City of Chicago's Department of Business Affairs and Consumer Protection, play a role by offering programs, grants, and assistance to entrepreneurs, including those from under-represented groups. World Business Chicago also works to connect founders with investors and promote an inclusive tech ecosystem.

But what looks good on paper often proves more complicated in practice. Bureaucracy can be time-consuming and opaque, especially for first-time founders unfamiliar with local laws. Incorporation takes longer than expected. Accessing public funding often means navigating slow processes, strict requirements, or hard-to-reach advisors. And operational costs – from accounting to regulatory compliance – can quickly eat into early budgets. 

A System That Moves With You

With access to expert guidance, practical legal resources, and a network of experienced entrepreneurs who’ve built across a range of regulatory systems, EWOR is well positioned to help founders navigate the bureaucratic and legal complexities that often come with building in Chicago. Instead of wasting time figuring things out alone, you’ll have the tools and support to stay focused on what matters most – growing your venture.

And while we’re remote-first, our support is anything but distant. Through in-person gatherings like the EWOR House, city-based meetups, and our twice-yearly Grand Pitch event, you’ll still build meaningful relationships with investors, peers, and mentors. It’s a system that helps you focus on building – not just dealing with paperwork.

Can Chicago Be Considered the Best Place to Launch a Startup?

There’s no doubt that Chicago provides a vibrant environment for startups, with access to funding, innovation, talent, and infrastructure that can help entrepreneurs build successful businesses. For many, it’s a strong contender for the best place to launch a startup, thanks to its growing entrepreneurial ecosystem and support systems.

Entrepreneurs launching a startup in Chicago may face several challenges. Competition can be significant in Chicago's growing tech and business scene, with over 1,600 active startups and numerous established companies. While Chicago's cost of living is lower than some major tech hubs like San Francisco, it can still impact startup salaries and overall operational costs. Regulatory issues pose another hurdle, involving complex licensing, permitting, tax obligations, and compliance with various city and state laws. Navigating these regulations requires time and resources, potentially impacting a startup's ability to compete and scale.

However, it’s important to remember that the location of a startup is no longer the be-all and end-all. In today’s digital age, location-independent options like EWOR allow entrepreneurs to access world-class mentorship, funding, and resources from anywhere in the world. Whether you’re based in Chicago or elsewhere, EWOR’s remote programmes are designed to support founders no matter where they are located.

So, while Chicago offers significant advantages, it’s worth considering options like EWOR that enable you to launch and scale your startup with global support – whether you’re in the heart of a bustling startup hub or working from a quiet corner of the world.

Image credits: by Andreas Brücker on Unsplash