10 Chicago-Based Startups To Keep An Eye On

Opternative offices | Courtesy of Opternative
Opternative offices | Courtesy of Opternative
Chicago has proven itself to be a successful startup haven, and there are more small companies popping up around town than can be counted. Some are complicated and tech-centric, but others could have a real impact on your everyday life. And nearly all of them have an app you can download. Check out this list of the best useful startups Chicago has to offer in 2016, and keep an eye out for them before they blow up nationally.


Gesture has streamlined the process of raising money through silent auctions in one convenient mobile app. The basis of their startup is acknowledging how ‘one small gesture can make a huge difference.’ They partner with organizations and causes looking to encourage giving. You can digitally ‘attend’ different silent auctions and bid on items, letting your money go toward a good cause. To date, they have worked more than 4,000 events and raised more than $290 million.


BookedOut is a multi-purpose marketplace app that helps you get your hustle on. It’s becoming increasingly common for people of all ages to want to earn money on the side of a current job, and BookedOut is helping to expand that beyond driving for ride-sharing companies or nannying in the neighborhood. It focuses on freelancing with a special interest in event attendance. Download the app, create a profile, pad it with résumé-style information and apply for available gigs in your area. You might help promote a new soda flavor for an afternoon or set up a brand’s event. You could even sample products or demonstrate new technology. Once booked, the app takes care of communication, directions, tips, and even payment.


Pearachute is all about catering to your little ones. It’s an app that shows you all the best classes, events, and activities for kids around Chicago. Pay $39 per month and get free access to any three classes of your choosing. They also offer more expensive plans for six classes per month or even an unlimited plan. It’s perfect for the parent looking to get their kids involved in new things. You can use it to find your child’s new obsession or just to keep your family active during the chilly winter months.


AptAmigo is technically an apartment search engine, but it manages to separate itself from the likes of Zillow, Domu, and Here, you’ll find in-depth reviews of selected apartment buildings in Chicago, covering more than just bedroom count and square footage. Learn from previous tenants about building security, creaky floors, water pressure, thin walls, elevator efficiency, and more. It’s a great resource if you’re hunting in one of their focused neighborhoods, but keep in mind that they’re only present in a select few. Use them to discover building info in places like River North, Gold Coast, Lincoln Park, Lakeview, Hyde Park, Old Town, and the Loop.


BallotReady sprung up during this election season as a way to ‘create a more informed electorate and strengthen our democracy by helping voters vote informed, all the way down the ballot.’ Their idea is simple: input your registered voting address, and they show you your entire ballot for the general election coming up on November 8th. We all know the presidential candidates, but what about the dozen circuit court judges that need your vote? The ballot is often long and filled with names you don’t recognize and on which you aren’t informed. But at BallotReady, they show a biography of each candidate and include their stances on important topics, public endorsements, and activity in the news. It’s the best place to research before voting and to locate your polling place.


Brideside appeals to the far-flung bridal party. They recognize that while your wedding is in Chicago, your bridesmaids might currently live elsewhere. And weddings get expensive very quickly for the bridal party. It’s not always an option for your friends to fly across the country to try on bridesmaids dresses and attend fittings. That’s why Brideside offers the chance to create a digital closet to share with your bridesmaids and shop together, though you may be thousands of miles apart. An assigned style consultant will work with the bride to choose dresses and colors before mailing them out to try-on.

Opternative, Inc.

If the thought of waiting at an eye doctor’s office, picking out new frames, dealing with prescriptions and insurance sounds like a headache to you, Opternative may be your solution. They offer a patented IRB-approved side-by-side clinical trial eye exam that you can take from your couch. It’s all online, and it’s proven to be accurate. Once you take your test that’s guaranteed to cost less than your ophthalmologist’s, you get a prescription and have the freedom to shop anywhere for your frames and lenses. It’s super simple, and they boast a 99.6 percent satisfaction rate with excellent customer service.

Opternative offices Courtesy of Opternative


Cliq takes the guesswork out of meeting new friends and does the heavy lifting for you. It’s an app that you join with your real-life friends to meet other groups of friends nearby. Once you connect, it sets you up in a large group chat to plan an outing. See a comedy show, hit a bar or find new concert friends. No matter what you choose to do, Cliq makes sure you cross paths with new, fascinating people that are just as excited about exploring Chicago as you are.


CloudSpotter powers SpotMyPhotos, which is a professional photography business you can hire for your next event. But what makes it special is the accessibility of it all. Photographers capture your event, and assistants register your guests with the service. Those registered are then immediately sent every picture they appear in, leading to increased social engagement and event awareness. It eliminates the chore of your guests spending hours scrolling through hundreds of photos without them or ignoring the photos completely. Your money will never be wasted with SpotMyPhotos, and the images will be enjoyed by everyone.


If you need something moved, you don’t own a car, and an Uber just won’t cut it, schlep it. Schlep is a service that will do your heavy lifting. All you need to do is take a picture of the item (or items) you need moving, add a few details, get a price quote and book. Your schlep will be completed by one of Schlep’s trusted employees (they call them Schleppers) and can request with 3 hours, or even schedule up to two weeks in advance. Move anything you like, from furniture and appliances to artwork and antiques. Get Schlepping!