Chicago’s Most Influential Internet Startups Revolutionizing Industry in 2023

The Windy City, Chicago, is renowned for its rich history, diverse culture, and revered sports teams. Yet, this city of broad shoulders prides itself on more than just deep-dish pizzas and the iconic Navy Pier. Beyond the unmistakable architecture, Chicago has surged into the tech scene, giving rise to innovative Internet startups that are disrupting various industries. From cryptocurrency to e-commerce, social networking, music streaming, and more – let’s explore the wave of digital ventures defining the present and future of Chicago’s startup ecosystem.


Founded by Joel Birch, Path is a unique Chicago-based startup that modernizes the arcane world of cryptocurrency investment. An SEC-registered robo-advisor, Path leverages automation to optimize your crypto portfolio investing, making it accessible and efficient for all.


Bopdrop is an intriguing startup that taps into the transformative power of music. Brought to life by founder Matthew Krause, this application makes music sharing a seamless experience. With their innovative approach, Bopdrop is refining the way we engage with and consume music online.


In the realm of online dating and social networking, we stumble upon Yaass. Curated by Roushan Kumar, this innovative platform is fostering virtual connections between potential partners, providing a fresh take on the way we perceive love and relationships in the digital age.

Leafy Quick

Leafy Quick has carved out its own niche in the e-commerce arena by offering legal access to a plethora of CBD and endocannabinoid products. From oil and flowers to gummies, this startup is simplifying and streamlining the somewhat daunting CBD purchasing process.

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Helmed by Joe Lee, Inverse excels in creating tools to monetize online communities and events. Connecting the world of blockchain, the internet, and software, Inverse shines as a startup that’s truly pushing boundaries.


BellyMelly‘s unique approach to online ordering solutions and restaurant app services make it a key player within Chicago’s internet startup ecosystem. Their novel business model is adding an exciting twist to the food industry.


ProdRocket is an inventive startup studio that helps bring product ideas to life. Founded by David Britton, they are experts in validating, launching, and scaling delightful products, thereby bridging the gap between innovative ideas and tangible success.

Rocket Wagon Venture Studios

Rocket Wagon Venture Studios energize new entrepreneurs to build products, assemble teams, and strategize their entry into the market, offering indispensable guidance to those on the frontier of entrepreneurship.

Garrison Olson

The brainchild of Kyle Olson and Ryan Garrison, Garrison Olson specializes in connecting brands to their audiences innovatively and compellingly. Through their creative approaches in advertising, digital marketing, and PR, this startup assists brands in amplifying their message effectively.

Aboriginal Armadillo

Navigating the intricate worlds of artificial intelligence, machine learning, and software engineering, Aboriginal Armadillo is a startup founded by Trevor Grant. This startup is a pioneer in natural language generation and image processing.


Threehub is another exciting addition to Chicago’s burgeoning Internet startup scene. Although its specific focus within the Internet industry is not detailed, it adds to the diversity and innovative spirit of Chicago’s startup ecosystem.


Bloqdrop, a venture of Evan Luza, reduces the complexity of sharing social profiles by harnessing the power of dynamic QR codes. With a simple sweep of a mobile camera, connecting on various platforms is now easier than ever.

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GeneratorOn has made its mark in the Internet and Messaging industry. Although specific details about this startup are scarce, its inclusion in the list suggests a vibrant contribution to Chicago’s digital ecosystem.


Blueprint, co-founded by Daniel Freed, champions the use of technology in mental health care. It provides therapeutic professionals with personalized analytics, ensuring more effective patient treatment.


Roamli, co-founded by Bane Srdjevic and Brian Lee, equips organizations with advanced marketing tools. With its focus on creating branded experiences, it’s accelerating user engagement and revenue growth across numerous industries.

In conclusion, whether it’s in music, food, dating, health, or a wide range of other industries, Chicago’s startup scene is burgeoning with radical innovations. These startups not only showcase the dynamism and diversity of the Windy City’s business environment, but also signal the robust potential of the city as a future tech hub on a global scale.

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