Chicago’s Most Innovative Startups Today

During a recent talk in Chicago about the “state of the American Dream,” PayPal founder Peter Thiel — the San Francisco-based billionaire who bankrolled Hulk Hogan’s lawsuit against Gawker Media — implied that no extremely talented, tech-savvy individual with ambition should stay in Chicago. That got us thinking about all of the city’s bootstrapping entrepreneurs fueled by a dream and a steady supply of espresso who’ve made big strides, even within just the last five years. We’ve rounded up 20 innovative startups worth watching because they’re doing some seriously cool, impactful work in their respective industries, right here in the up-and-coming tech hub of Chicago (NYC and Silicon Valley be damned!).


What they do: Schlep provides last-mile logistics and heavy lifting on demand by connecting you to a network of trucks and muscle for large item delivery.

Most urbanites can get away with going without a car until they’re faced with the grim reality that moving heavy, large, or awkward-shaped stuff around can be a real pain in the tuchas. We don’t all have friends who will let us borrow their cars, but luckily Schlep is connecting people who have moving needs with dependable neighbors and certified Schlep employees who are able to help with the heavy lifting. Weight and distance factor into the costs, and Schleppers can pick up that new couch whenever it’s convenient for you — you can even schedule up to a month in advance. 

Shoe Drop

What they do: Shoe Drop is a tech-enabled company revitalizing the cobbler industry.

It’s not easy maintaining an impeccable wardrobe, but services like DryV dry cleaning prove people are willing to pay top dollar for convenience. Following suit, Shoe Drop is shaking up the footwear scene by partnering with dry cleaners, office buildings, and high-rise residential buildings to make shoe care and repair super-efficient for Chicagoans. With dropoff locations across the city, by-appointment pick-ups, and even a new River North shoe shine location, Shoe Drop’s services range from polishes and weatherproofing to sole recrafting so customers can get the most wear out of their shoes.


What they do: Radish delivers healthy, ready-to-eat meals on demand.

Since GrubHub’s inception, food delivery startups aren’t exactly a novelty in Chicago, but the Radish app delivers organic, chef-prepared dishes in 20 minutes or less. Those who are struggling to eat healthy can build an affordable, fresh meal by mixing and matching à la carte items for about $3-4 each from a menu that changes daily based on the availability of local farm-raised ingredients. You can track your meal (usually three courses, with a mix of proteins, vegetables, and starches for roughly $10-13) from the chef’s kitchen right to your front door.


What they do: Foxtrot provides on-demand delivery of everyday essentials in under an hour through a mobile app backed by retail stores.

Foxtrot is the corner store reimagined for the digital age. The company, which now has retail stores in Lincoln Park and the West Loop, touts a shopping experience of curated eats, booze, and other essential goods from local vendors like KovalIntelligentsia, and Lillie’s Q through a sleek mobile app. Top-notch collections even group must-have items for a quick meal or boozy brunch, which you’re guaranteed to receive within an hour of tapping “order” in the app.

Public Good

What they do: Public Good is a digital marketplace that connects people to local causes and nonprofits

Headed up by Jason Kunesh and Dan Ratner, two successful serial entrepreneurs who helped found Orbitz, The Point (later Groupon), and, the Public Good digital platform makes it easy for people to discover and support the causes and nonprofit organizations that matter to them. In turn, it gives nonprofits the modern, mobile tools necessary for spreading awareness, accepting donations, and measuring their impact in one place.

Zero Percent

What they do: Zero Percent is an online food-rescue platform that partners with restaurants and food vendors so they can donate fresh, surplus food to Chicago’s underprivileged population.

According to USDA estimates, 30-50% of all food produced is discarded. Meanwhile, one in six Americans have difficulty finding enough to eat. But the app-based Zero Percent is helping put perfectly good surplus food to use by connecting it to the people who need it most. Partner companies like Goddess and Grocer can donate nutritious food to local programs like Heartland Alliance’s Vital Bridges, which dispatches volunteers for meal delivery from its grocery centers. Best of all, it’s free for both recipient organizations and donors.


What they do: Tock is a dynamic, flexible, and transparent way to book restaurants.

Traditional table reservations are a hassle for everyone involved. Tock is a restaurant ticketing startup set to shake up the reservation game for both partnering restaurants (think Next, Aviary, and Alinea) and would-be patrons. The engineering team of Google and Apple veterans custom-designed a web-based platform to help restaurants eliminate no-shows by better managing bookings, tables, and guests — even gathering information for guest profiles to provide better service — in real time. Diners might need to pay a deposit to secure a booking, but scoring a table at a popular restaurant and even pre-ordering meals online to cut down on wait times makes the experience worthwhile.


What they do: SpotHero mobile app and website helps drivers reserve discounted parking on-the-go or in advance.

There’s nothing worse than reaching your destination and having to circle the surrounding city blocks for an hour just trying to find a place to park your car that won’t cost an arm and a leg or result in a big fat ticket. SpotHero might be on everyone’s radar at this point since the growing tech company has partnered with private garages and lots in 15 markets across the US. The app has helped shape the future of parking by allowing users to view rates, get deals, reserve spots, and pay with their phones wherever they might be headed.


What they do: Rippleshot helps banks better identify fraud for banks and merchants by uncovering merchant data breaches and stopping card fraud sooner.

Each year, payment card fraud costs US businesses billions of dollars. Rippleshot reduces over 25% of fraud losses for banks and merchants by using big data to mitigate these costs. The fraud analytics startup’s technology monitors millions of merchant and bank transactions daily to help catch fraudulent behavior before the problem worsens. Self-improving algorithms work proactively to pinpoint breaches faster to prevent losses, protect brand reputation, and safeguard cardholder security.


What they do: The Opternative online eye exam — taken in just 25 minutes or less with a smartphone, tablet or computer — is the most convenient way to get a prescription for glasses and contacts.

Opternative could be an eye care industry game changer; the startup makes vision tests super-accessible and affordable for those in need of glasses and/or contacts prescriptions. While they’re not meant to replace your ophthalmologist, the doctor-reviewed online exams are suitable between comprehensive, in-person check-ups once every two years. The more convenient exam can also be cheaper than many brick-and-mortars ($40 for a glasses or contacts prescription, or $60 for both) and they’re clinically proven to be just as accurate as traditional refractive eye exams.


What they do: Hearken is an audience-driven framework and platform that allows journalists to partner with the public throughout the reporting process.

How would the news coverage we read, hear, and watch today change if communities were more directly and actively involved with the reporting process? Co-founded by WBEZ’s Curious City creator Jennifer Brandel and Chicago startup veteran Corey Haines, Hearken is helping newsrooms across the nation welcome a new era of audience-driven journalism — from lead generation to story selection and angles — resulting in more relevant and high-performing content.


What they do: Infiniscene is changing the live video streaming production scene with its simple, powerful, and collaborative online platform.

The live streaming video game industry is exploding now, and Infinscene has big ideas for the sector’s future. Its intuitive, cloud-based broadcast studio helps aspiring streamers easily broadcast professional-looking shows, so they can focus more on gaming and audience engagement. A recent launch out of beta rolled out new multiplayer streaming and remote collaboration features, and soon a mobile broadcaster will give users the power to broadcast mobile games to their Twitch channels or go live from the show floor at TwitchCon or PAX.


What they do: Kapow helps companies book venues online and manage events from start to finish in real time.

Planning a killer corporate party, dinner, or huge event can be a logistical nightmare. But Kapow’s curated online marketplace and suite of tools is saving companies, including Google, LinkedIn, and HP, the headache of hosting the perfect holiday soirée. The platform is changing the corporate events game by helping companies more efficiently find and book unique venues as well as manage events designed to acquire, engage, and retain clients.


What they do: Orunje is an online platform bringing local healthcare providers to your home, office, or hotel room.

Stuck in bed with the flu? Orunje is putting a tech-enabled spin on an old concept: the at-home doctor visit. Whether you’re at home, in the office, or even staying in a hotel room, a licensed physician or nurse practitioner from the Chicago startup’s network of registered providers will come to you within two hours of placing an electronic request. Exceptional healthcare shouldn’t have to come at a cost; affordable flat-rate pricing ensures there won’t be any sticker shock for treatment regardless of visit complexity or insurance policy.


What they do: Raise is the world’s largest gift-card marketplace. Buyers can save at their favorite stores, and sellers can earn cash for their unwanted gift cards.

As one of the fastest growing e-commerce companies in the nation, Raise is revolutionizing the retail industry by putting the purchasing power back into the hands of the consumer. The easy-to-use, peer-to-peer marketplace gives savvy shoppers the ability to buy and sell gift cards and store credit at a discount from retailers ranging from Target and The Home Depot to Macy’s and Gucci via the mobile app or online.


What they do: Reverb is the online marketplace for musicians to buy, sell, and learn about music gear.

Reverb is the go-to site for musicians buying and selling music gear. The music tech startup developed a solid marketplace built on community and technology, and the online destination has quickly become one of the best places to find and sell vintage, rare, handmade, and other used music gear — all browsable by city, country, and brand. The company has also launched a successful video channel with original content like a “Learn to Play” video lesson series, and has become a space for users to connect with local instructors for online or in-person lessons and explore music-related news and tips for novices and professionals.

LifeLine Response

What they do: LifeLine Response is an on-demand security service accessed through your smartphone.

When dialing 911 in the event of an attack, it’s often assumed you can verbally articulate what is happening. LifeLine Response, a safety awareness and security-focused startup, doesn’t make this assumption. The smartphone app-based safety service immediately alerts authorities when you’re in danger, even if your phone breaks during a struggle. The company eventually hopes to deploy drones — activated within 15 seconds of when police are notified — to provide law enforcement with real-time video surveillance to monitor the situation while en route.


What they do: Curiosity helps people learn something new every day.

With a mantra to “never stop learning,” Curiosity is a tech and creative startup in the business of revolutionizing lifelong learning. and its companion app aggregates and organizes a range of videos, articles, talks, and more from around the web for the intellectually curious. They’ve hand-picked the best consumer-friendly educational content from creators like Bill Nye, Discovery Channel, Google, Harvard University, the Chicago Botanic Garden, and more to give knowledge seekers the most interesting learning experience in a mobile-friendly format.

4D Healthware

What they do: 4D Healthware is a health technology enterprise that monitors your personal health and delivers care recommendations based on real-time data.

4D Healthware wants you to know you’re sick, even before you experience any symptoms. Through activity trackers, wireless scales, and wearable biometric sensors, the company — which is based out of Chicago’s healthtech incubator MATTER — can monitor your personal health in real time. Patients receive timely care and lifestyle recommendations in a viewable dashboard along the way.


What they do: LyteShot takes gaming out of the living room and into the real world.

Launched by gaming industry veterans, LyteShot is a hardware, software, and platform-based company designed to operate in a 3D world. The company created a new market segment called “live action gaming.” The augmented reality-based mobile gaming platform is built around a mobile app and sensor-based device so users can play games in physical spaces. Their first game, Assassin, is an action shooter experience that lets players go into their city or neighborhood, search for friends, and fire the sensors once a target is spotted and in-range.


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