50 Chicago startups to watch in 2016

Written by Andreas Rekdal
Published on Feb. 01, 2016
50 Chicago startups to watch in 2016

Judging by the numbers in our 2015 Chicago startup report, Chicago tech just had its best year ever. This city was built on industry, however, so there’s no reason to think the tech community is about to rest on its laurels.

Which companies will be at the vanguard of Chicago’s innovation in 2016? Just like last year, we’ve picked 50 startups we think are worth watching. To be included in our list, companies had to be digital tech-centered and founded within the last five years.

While startups like Uptake, Avant, Raise, Kapow, Civis Analytics and Reverb.com certainly fit these criteria, we suspect they’re already on everyone’s radars. We’ve decided to leave them out (along with some other young Chicago A-listers) to make room for some exciting newcomers.

Expect to hear more of these 50 names in the year to come.


The risk of spreading disease and infections can make hospitals dangerous places to be. SwipeSense is a hand hygiene system that captures usage statistics through badges worn by caregivers. The company’s software allows hospitals to monitor hygiene compliance on a unit — or individual — level, encouraging employees to form lasting habits that prevent the spread of disease. With the annual cost of hospital-acquired infections in the billions of dollars in the U.S. alone, there should be plenty of demand.

In the news: This summer, this Moxie winner raised $9.7 million.


Want to put on a fundraiser or an auction? Gesture is here to do your bidding. The company’s mobile platform digitizes the silent auctioning experience, and lets donors participate in your auction even if they can’t make it there. Having raised more than $225 million from over 900,000 donors and counting, Gesture’s mobile auction platform is definitely on the up-and-up.


In the retail business, few things are as costly as unmoveable inventory. DRIVIN (acquired by KAR) takes a big data approach to used car sales by analyzing information about local market trends and used cars available to dealerships. In addition to sorting out undesirable cars and helping dealers stock their lots, DRIVIN also helps dealerships find the right price point for each car to keep that inventory moving. And with their new iOS app out, it’s never been easier for dealerships to jump on the bandwagon.

New VP at the wheel: Lisa Killeen, formerly of LinkedIn and CareerBuilder joined DRIVIN as VP of sales in January.


It’s rare to find a company — startup or not — that’s laser-focused on a single purpose. But then, not every company is like Pangea — a company making it easier for immigrants to send remittances back to their home countries, helping citizens of developing nations put food on the table. With Pangea's mobile app, money transfers can be made with any major US debit card in less than 30 seconds. At the moment, Pangea focuses mainly on the US-Latin American corridor, with more global ventures likely on the horizon.


With its long history as a logistics hub, few cities are more appropriate for a shipping startup than Chicago. To compete in the crowded no-hassle shipping space, this Y Combinator-backed B2B startup cranks the convenience up by packaging customers’ items and shipping them through the most affordable service available. Having already expanded to New York after its founding in 2014, ShipBob’s fleet of Ship Captains will soon be delivering packages across an ocean near you.


Marketed as the Uber for document review, Esquify saves companies and law firms money by offering digitally supervised virtual case reviews by barred and rated attorneys. Launched in October 2015 with angel funding, the 14-person company (and growing) has experienced a doubling in customer base every month of its existence, and is in talks with a well-known Chicago tech incubator about plans for 2016.


Determining eligibility for social services can be a major barrier of entry for those who need them the most. To help people overcome it, mRelief has partnered with the City of Chicago to let residents check their eligibility for programs via text message or through a simple online application. Being accessible via text message is particularly important since many who are eligible for social services use cell phones with limited internet access. With a recently launched tool that lets service providers create their own simple screeners, mRelief is poised to make an impact in the year to come.

WiSTEM members: This summer, mRelief co-founder Rose Afryie was named a member of the inaugural class of 1871’s WiSTEM initiative alongside Mumzy's Catherine Merritt (see below), among others.


Need new glasses? Opternative lets you get a vision test without sacrificing your lunch hour. Take a 25 minute online exam, wait 24 hours for your digital prescription, and shop around for glasses wherever you want. It may sound too good to be true, but an IRB-approved side-by-side clinical trial found that Opternative’s test was equivalent to a traditional refractive exam. At $40, the test is cheaper than most brick-and-mortar options too, so we may find ourselves on the brink of a major industry disruption.


Looking to bolster your brand on Instagram? Popular Pays connects brands with popular Instagram users offering to promote their companies for a fee. After you specify what you want from the campaign, Instagram users make offers that are displayed alongside their photo streams and stats about follower bases. Once you’ve chosen your Instagrammers, the platform lets you track your campaign’s impact, enhancing transparency throughout the process.

If you pay for ads on a per-view basis, you may be wasting a large percentage of your budget on showing your ads to the wrong audiences, on the wrong sites, or to bots — and bots don’t buy whatever it is you’re selling. AdYapper provides tools for tracking how many of your “views” are generated by engaged human viewers, helping ad buyers eliminate low-returning buys from their portfolios, reinvesting the savings in what's working. The company does so by measuring whether ads are displayed visibly on the page, how long viewers are exposed to campaigns for, and how customers interact with them.

In the past year: AdYapper raised a $4.5 million round to expand its global reach.

Akouba Credit helps local brick-and-mortar banks offer credit to small businesses at competitive rates. A member of the Techstars class of 2015, this company reduces the cost of offering such loans by automating much of the underwriting process, bringing local banks up to speed in the competition against nationwide online lenders.

In the past year: Akouba Credit was one of 10 startups in the Chicago Techstars class of 2015.

As any small business owner will tell you, managing appointments and billing is practically a whole other job on top of the job you’re already supposed to be doing. Some professions, including personal trainers, have it especially rough, which is where amSTATZ comes in. The company's personal trainer software provides an all-in-one app with payments, records keeping, scheduling and goal tracking. The app also lets trainers assign workouts to clients with due dates and reminders, helping to keep their eyes on the prize.

Want the inside scoop on your next apartment building before you sign a year-long lease? Aptamigo connects apartment hunters with current and former tenants to help newcomers find the kind of digs they’re looking for. Beyond beds, baths, square footage and nearby amenities, AptAmigo gets into the nitty gritty, with info about things like water pressure, light, temperature control, WiFi and privacy. And if you’re wondering about the overall “feel” of the neighborhood and building, this 2015 newcomer has got you covered there too.

As the 2016 presidential race continues to rear its political head, BallotReady is positioning itself as a valuable tool for voters who want to make the most informed decisions possible. The startup's free, online platform helps voters sift through partisan noise, arming them instead with unbiased research on every local candidate and referendum on the ballot. By aggregating information from across the web, this startup lets users search and compare candidates by the issues that matter most to them. Launched in 2015, the company is on a mission to inform one million voters by year’s end.  


Joining Chicago’s family of curated apparel services, Brideside helps bridal parties choose dresses for the special occasion. After the bride sets up an account and indicates the styles that fit the wedding’s aesthetic, a dedicated stylist will help bridesmaids pick out dresses that fit them. The stylist ships up to three dresses for each bridesmaid to try on before picking one. With many bridal parties dispersed all across the country, this startup just might help bring down the cost of attendance for bridesmaids who’d otherwise have to travel to go dress shopping with the rest of the party.

“Brunch?” It’s is a simple question that shouldn’t require digging through your entire contact list. The Brunch app is a geolocation-enabled message board that allows you to invite nearby friends to join you for, well, whatever. Messages get deleted after eight hours, so there’s no need to sort through your post history to delete old concert invites when you make new, cooler friends.

It can be hard to gain traction as a social media app in a city dominated by B2B tech ventures. Cliq managed to catch the attention of investors to secure enough capital to get the ball rolling. The company’s app aims to spruce up your social life by providing groups of established friends an incentive to meet new people and explore the city. With Cliq, disparate social cliques can mingle and meet in group chats before meeting in person. If everyone really hits it off, you might even trigger a special “Cliq Event,” like drink specials at a nearby bar or tickets to a concert.

Related: Best Startups to Work for in Chicago

Rather than have event attendees dig through photo albums for pictures of themselves, CloudSpotter’s event photographers automatically send people the photos they’re in. Add the option for guests to instantly share the pictures they like on social media, and you’ve got a recipe for some solid organic marketing of your events. People will probably continue to enjoy looking at — and sharing — pictures of themselves in 2016, meaning the future’s looking bright indeed for this event tech startup.

Having spent their entire working lives in uniform, many veterans of the United States Armed Forces struggle finding suitable jobs when they retire from service. Code Platoon is a developer bootcamp that seeks to help veterans get the most sought-after skills in the American job market. With no previous programming experience required, Code Platoon’s nonprofit structure helps it make bootcamps more affordable for veterans too.


Sure, demographics are important in social marketing. But sometimes, when you reach someone is just as important as whom you’re reaching. You wouldn’t want to spend your entire ad budget for artisanal hot chocolate on an unseasonably warm Chicago day, would you? Earshot synthesizes location data with other available information to help brands better target their precision marketing. And with its proprietary “Decibel Level” algorithm, brands can choose which factors are most important to their customers.


First dates are almost always awkward. In addition to fretting over what to do and where to go (and what conclusions your counterpart may draw about you based on those choices), there’s the question of what conversation topics to bring up in order to come off as interesting, but not pretentious. Enter FanMatch, which lets you plan to meet up with other people who are already attending the same concerts and events you are, leaving you with an instant shared interest to geek out over.


What would the news look like if audiences were more involved in the reporting process? That is the question upon which this Chicago startup is built. Founded by WBEZ veteran Jennifer Brandel, Hearken helps newsrooms bring community involvement into every part of the process, from lead generation to deciding which stories to cover and what angle to take.

Accelerator darling: Launched in 2015 and a graduate of San Francisco’s Matter accelerator, Hearken is headed to SXSW’s Accelerator pitch competition in March.

While medical marijuana is now legal in nearly half of the country’s states, cannabis companies are still subject to enough complex zoning regulations to give a budding entrepreneur cotton mouth. In addition to having to avoid schools, daycare facilities, and residential areas, many new businesses will find that landlords can be reluctant to sign on all cash businesses who run afoul of federal law as tenants. HerbFront helps companies in the marijuana industry find open-minded landlords peddling properly zoned real estate.

Related: The Coolest Tech Offices in Chicago

Between gamecaster PewDiePie’s two year reign at the top of YouTube’s subscription charts and Amazon’s acquisition of game streaming service Twitch, watching other people play video games is rapidly working its way into the American entertainment mainstream. This Chicago-based Techstars graduate helps aspiring streamers broadcast professional looking shows with ease, leaving them to focus on gaming and audience engagement. Infiniscene also lets users create more advanced setups, like multiplayer streams, waiting screens, and more.

In the news: Infiniscene is a member of the Techstars class of 2015.

Market research can be expensive, but some business decisions are too important to leave to chance. KnowledgeHound gathers existing market research and makes it available to its customers in an easily searchable database. The data is presented and visualized in a simple and intuitive way, saving sales teams and marketers both time and money. And by reducing the need for automated phone surveys, KnowledgeHound’s proposition should be a win for consumers as well.

Ever gone to an event only to spend half of the time trying to find friends who arrived late, went to the bathroom, or headed off to get more beer? MeetBall’s social crowd navigation app might be just the solution you’re looking for. When attending events, you and your friends can set waypoints for locations to meet up, navigating with a video-game inspired built in compass. Recently relaunched to rave reviews in the Apple app store, MeetBall is likely to be in for a great year.

Until we reach the Singularity and AI robots start reproducing, we puny humans will be stuck building and training them to do our bidding. Motion AI makes that process easy, with flowchart-based user friendly interfaces that let you create an AI that will take delivery orders for your taco stand via text message, sell movie tickets via email, handle customer service requests in a chat window, and more. Founded by serial entrepreneur David Nelson, the company’s promising a pay-per-message service with a low price point, making AI available for the masses.


MUMZY is a crowdsourcing platform specifically for moms. In the wake of an attempted launch of a product that would turn any handbag into a diaper bag, the company’s founder asked herself why there aren’t more resources out there to help moms bring their ideas to life. Unlike other crowdfunding sites, which ask entrepreneurs to draw heavily on external networks, MUMZY seeks to build a community of entrepreneurial moms who offer guidance and assistance to each other along the way from concept to creation.


You’re already getting your rides, food, books and TV shows on demand, so why not your shots and annual checkups? Founded by physicians and a healthcare informatics PhD, Orunje brings healthcare providers to you. The at-home doctor visit may be an old concept, but Orunje’s tech-enabled take makes it exciting nonetheless.

Are your selfies so good you feel like someone should be paying you for them? With Pay Your Selfie, this dream can become reality. The idea is simple: brands pose selfie challenges with cash rewards, and users get paid up to $1 for their photos.

Looking to attract and retain highly educated, tech-savvy talent for your company? Offer to pay off their student loans. Peanut Butter helps companies provide student loan repayment to their employees as a benefit. Once you enroll an employee, Peanut Butter verifies their student loans and takes care of the payments for you. That way, they won’t have to worry about accidentally spending it on Uber rides.


Chicago’s becoming somewhat of a mecca for food delivery startups. With tech standards like GrubHub blazing the trail, it’s not hard to see why. Launched in 2015, Radish allows users to order organic, locally grown meals à la carte from a menu that changes daily. Meals start at about $10 and are delivered in under 20 minutes as an eco-conscious and health-considerate alternative to many other food delivery apps.

Payment card fraud costs American businesses billions of dollars annually. Rippleshot uses big data to mitigate these costs by nipping payment card breaches in the bud. By sorting through millions of transactions, their self-improving algorithms find shared shopping history among cards that have been breached. With its recent infusion of $1.2 million from investors, we’re looking forward to seeing what 2016 holds for Rippleshot.

Wearables are likely to continue growing in popularity through the next year, but if manufacturers want their devices to become permanent fixtures of our lives, they’ll need to ensure their tracking features work well for everybody. Enter Rithmio — a platform for motion-sensing devices such as wearables or connected clothing. Rithmio’s software gets to know its users over time, with the aim of being more accurate for a variety of users than one-size-fits-all-trackers.

With digital initiatives from public radio giants like NPR and WBEZ on the rise, there’s no longer much doubt that the future of radio will be online. But music streaming services and podcasts are an incomplete substitute for the horizon-broadening potential of a full-fledged radio station. Rivet Radio offers a curated mix of news content with topics including sports, business, politics, science, and arts.

Broadening your horizons: Through its recently announced partnership with Mood Media, Rivet may soon be providing news updates in a store or hotel lobby near you.

For many urbanites, schlepping heavy and awkwardly shaped stuff around is pretty much the only remaining reason to have a car. This startup connects people with schlepping needs with local truck owners who aren’t afraid to lift a couch or two. With scheduling options for up to a month in advance, you can pick up that Craigslist furniture whenever’s convenient for you.


As dry cleaning startups like DRYV and Washio have shown, people are willing to pay a premium for convenience in keeping their wardrobes on par. Shoe Drop offers similar convenience for footwear maintenance, with drop off locations across the city and by-appointment pickups. With services ranging from polishes and weatherproofing to sole recrafting, Shoe Drop can help customers keep their shoes longer, reducing waste and saving their money.

A healthy employee is a productive employee, or so the adage goes. SnackItToMe! creates custom snack plans for organizations, and ships treats on a weekly, bi-weekly or monthly basis. Subscription box services and health foods are both on the rise, and snacking is a timeless classic. What’s not to like here?


With more than half of online traffic coming from mobile devices, responsive design is more important than ever. But creating separate ad campaigns to fit every device under the sun is a massive waste of your creative talent’s time. Specless automates the grunt work of creating responsive ad campaigns by adapting a photoshop file to fit many different sizes and devices. Once the heavy lifting has been done, users can tweak the design inside the company’s proprietary web interface and rest easy that their campaigns will look good across devices and platforms.

In the news: Specless was a member of the Techstars class of 2015.

Looking for a new take on fantasy sports competitions? SportsLock has carved out a niche for itself as a middle ground between the immediacy of daily fantasy and time consuming season-long fantasy leagues. Its core competition is a “survivor” bracket, where players choose four new athletes for each round and play head-to-head against other players. Investors include former MLB COO Robert Duputy.


One of the big gripes people had in transitioning from button-operated cellphones to touchscreen devices was the loss of tactile feedback when typing. Tanvas is bringing back that responsive feeling without bulking up your device or shrinking your screen. They’re also working on completely new immersive uses of touchscreens, like feeling the texture of materials and getting tactile feedback from objects in video games.

In the news: Tanvas raised $5 million from investors this summer.

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Traditional table reservations are terrible for everyone involved. For some popular restaurants, would-be patrons need to call in at exactly the right time, weeks — or even months — in advance to pick up a reservation. Yet despite this hassle, a large percentage of reservation holders still fail to show up. Tock is looking to make the experience better for both parties by letting diners pick up reservations and order meals online in advance, reducing wait times and no-shows, and increasing capacity for restaurants. With exciting high end Chicago partners including The Aviary and Alinea, we may see this startup move to new markets in 2016.

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Tribe is an automated task manager that lets you create new tasks by sending emails or cc’ing it in your correspondence with others. Emails include links to mark tasks as done, eliminating the need to download software. Since everyone uses email, Tribe is ideal for managing contractors, freelancers, babysitters, and loved ones.

On task: A member of the Techstars class of 2015, Tribe’s definitely checking boxes on its own to-do list.

Why can’t booking an eye exam from a local eye doctor be as easy as ordering food from GrubHub? That’s the question that led to the founding of Whittl — an app-based appointment booking service for local businesses in pretty much every vertical imaginable. After raising $3.3 million this summer, Whittl launched in Boston in October with over 100 participating businesses and is preparing to expand to additional markets including Washington D.C. and New York City.


As advertising continues to become more and more ubiquitous, people are getting better and better at tuning it out. One way brands are seeking to counteract this trend is by integrating their products into the content people want to consume. Wordperks brings this approach to the grassroots level by offering special deals to social media users who promote participating brands through their accounts. Maybe next year you’ll be boosting your latte art Instagram feed with a free cup or two.

Did you know that between 30 and 50 percent of food produced is discarded? Zero Percent, an app-based solution for donating surplus food, is working to bridge the gap between companies seeking to avoid food waste and nonprofits that provide food to people who need it. The service is free to use both for recipient organizations and donors, but the company offers detailed donation data for tax savings purposes as a premium service. With endorsements from nonprofits like Salvation Army as well as Einstein Bros, the bagel purveyor, this company is definitely one to watch.


Do you remember the part in The Big Short where Brad Pitt’s character made his friends call him back repeatedly to make sure they were talking on a secure line? Had he used Green Key Technologies’ software, that whole ordeal could have been avoided. Green Key makes encrypted voice communication software for brokers and traders that requires no physical phone lines and makes it easy to merge calls, enable “push to call” features for large conversations, and mark yourself as online or offline.


OfficeLuv was one of the very first companies unveiled by Paul Lee’s newest venture, a startup factory called Ronin. They’re on a mission to bring office cleaning and management into the digital age, with a product that allows businesses to centralize and automate as much of an office’s maintenance and cleaning services as possible. Despite having launched just last year, OfficeLuv is already growing fast.


As both employers and workers continue to seek more flexibility in scheduling, BookedOut connects event organizers, salespeople, and brand ambassadors with companies looking to put on events. After creating a profile, freelancers can apply for event gigs, prep, get updates and notifications, bill hours and get paid — all through the company’s app. Judging by the number of Lyft and Uber drivers out there, plenty of people want to make money on the side. BookedOut lets those without cars be part of the craze.


Founded by Desiree Vargas Wrigley, founder and former CEO of GiveForward, this startup helps parents discover activities for their children that fit into their busy schedules. With options for an unlimited number of classes for $99 a month (though capped at three classes per studio in a 30 day period), Pearachute is a great option for parents of children who love to try new things.

Related: Best Startups to Work for in Chicago

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