The investors guide to: Chicago

America’s Second City has one of the world’s most recognisable skylines and one of the most historic music scenes, stretching from jazz and blues to house, and Chicago is also home to one of the biggest local startup scenes in between the country’s coasts.

AI-equipped cancer drug developer, online lender Avant, precision medicine producer Tempus and online insurance provider Kin are among the unicorns to have emerged from the city, and its local corporates include Allstate, United Airlines, AbbVie and McDonald’s.

But what exactly is it like to be an investor in the Windy City? We asked Madelyn Rutter (below), senior director of collaboration for corporate-startup venture collaboration platform TechNexus Venture Collaborative (and co-founder of local venture capital network V2:VC), to fill us in.

What makes Chicago’s startup scene stand out?

Chicago might not be the first US city that comes to mind when you think of startups, but it should be. What sets this ecosystem apart is that it’s not built on buzzwords, it’s built on industry. Logistics, manufacturing, insurance, healthcare, food — founders here are solving real problems for real customers. And with one of the most diversified economies in the country, Chicago offers stability and staying power.

Startups here have direct access to Fortune 500s, national labs, and one of the country’s top tech talent pipelines (the University of Illinois ranks third in the US for computer science graduates). Capital goes further, and companies are built with operating discipline from the start, surrounded by customers, partners and investors who understand scale, systems, and how to build businesses that last.

What makes it work? A grounded, collaborative culture where traction is the focus and support is baked into the ecosystem. If you’re looking for real opportunities in the industries that move the world, this city delivers.

Where are the hotspots in the local tech scene?

I’m biased, but I also just get to see the throughline. So many of the serious conversations and real work in this city are quietly happening inside TechNexus. TeamWorking by TechNexus is Chicago’s venture clubhouse where founders, corporate innovators, and investors actively collaborate. Especially strong for startups in hard-to-disrupt industries like industrials, mobility and enterprise software.

But we’re part of a larger story. mHUB continues to lead the way for hardtech and industrial founders. It’s a community that understands the patience and precision physical innovation takes. Portal Innovations and Fulton Labs are putting Chicago’s life sciences sector on the map, drawing scientists, clinicians, and founders into its health innovation hub.

Drive Capital hosts events like its AI Tinkerers meetups to connect the city’s AI builders. And The Polsky Center at UChicago is one of the city’s most powerful engines for deep tech commercialization in climate, quantum and energy.

Where’s the best place for a coffee meeting?

Kinsley if you’re near the Loop, Blue Bottle for a River North meetup, Sawada Coffee when you’re around Fulton Market, Espresso and Milk if you’re on the move — grab and go, then start your walk-and-talk on the Riverwalk at Lake & Wacker. Chicago’s full of great spots, but these are my go-tos when I’m downtown.

Where would you take a founder you wanted to impress to dinner?

Honestly, impress is in the eye of the beholder. For me, it’s less about star ratings and more about creating the kind of atmosphere where a great conversation can happen.

That said, Chicago makes it easy to get it right. You can’t go wrong with a Stephanie Izard spot like Cabra or Girl & the Goat. If I want something with ambiance and exceptional food, Monteverde, Bavette’s and Rose Mary are solid picks. If it’s someone who appreciates craft and detail, Kumiko is a standout for a nightcap. Want a view? London House (right) never misses.

With this city’s range, you can match the meal to the moment and still leave ‘em wowed.

What are the best events for meeting local founders and investors?

For investors, I’ll start with V2:VC — a peer community I co-created for Chicago’s pre-partner venture professionals. We host curated gatherings throughout the year designed to make it easier to build real relationships in the industry. The upcoming TechChicago Week (July 21–27) brings together the entire ecosystem and has become a key moment on the calendar every year. The crew at Chicago:Blend also puts on standout events for founders and investors, always with a thoughtful focus on representation and inclusion.

At TechNexus, we launched the Reinventing Industry Event Series earlier this year to spark more focused, sector-specific conversations. Highlighting where Chicago is truly leading across areas like clean energy, supply chain, and future of workforce. To stay plugged in year round, check out the CHI IRL events calendar or subscribe to Top 10 in Tech: Chicago — a biweekly roundup we publish at TechNexus featuring tech news, venture deals and must-attend events.

What’s the one thing every visitor should see while they’re here?

You’ve got to check out the lakefront. If you’ve never seen the Great Lakes, it’s a little mind-bending. Lake Michigan stretches endlessly like an ocean, with the city skyline right on the edge. You forget you’re in the middle of the country.

Between the beaches, bike paths, running trails and green space, it’s the city’s front porch. The Chicago River weaving through downtown only adds to the magic. Take an architecture boat cruise through the river to see the city in all its beauty — it’s the one tourist hot spot even locals love.

And if you’ve got a few hours, wander through the Art Institute of Chicago. It’s been called the best museum in the world for a reason. World-class galleries, iconic works, and my personal tip: don’t skip the Thorne Miniature Rooms. They’re quietly one of the most enchanting corners of the whole place.

Who in the VC/CVC/startup scene should people make sure to meet while they’re here?

Start at TeamWorking by TechNexus — grab a coffee and chat with our founders, Fred Hoch and Terry Howerton. Twenty years ago, they paved the way for much of what exists in Chicago’s tech scene today and haven’t taken their foot off the gas since. They’ve seen (and built) a lot.

The Innovation & Venture Team at World Business Chicago, led by Abin Kurikose and Nicole McCarthy, are true ecosystem builders promoting a pro-Chicago mentality and focus on making Chicago’s tech ecosystem more accessible, inclusive and connecting local founders with the biggest businesses in town.

And for a sharp POV on investing in the Midwest, grab time with Abhinaya Konduru, partner at M25. She’s got insights to share from Lincoln to Lansing. This team knows the region better than most.

Joey Mak at Chicago:Blend is a key leader pushing Chicago’s VC/CVC scene to be more inclusive and it’s working. Chicago is outpacing national averages in representation across race and gender, especially at first-time funds. Chicago:Blend’s tireless efforts and fellowship program are a big reason why.

Spend the day bopping around to those Chicago tech hotspots I mentioned earlier. Midwest nice is real, and folks at every one of these places will happily introduce you to even more people you need to meet (and probably make the intro, too).

What’s a secret only the locals know about?

Chicago is actually super easy to get around. It’s one big grid. Don’t be intimidated by public transit (CTA). You can be in a totally different neighbourhood, vibe and flavour in under 20 minutes. So, ditch the deep dish pizza and spend the day eating like a local instead:

Breakfast: Authentic Puerto Rican breakfast sandwich + coffee at Café Colao in Humboldt Park.

Lunch: Italian beef (yes, dipped with hot peppers) at Johnnie’s Beef in Elmwood Park.

Dessert: Swing back to Logan Square to hit the walk-up window at Miko’s Italian Ice.

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