Valentine’s Day is fast approaching. For some, V-Day is a time for reaffirming your love and celebrating your significant other. For others, it’s an over-priced holiday fueled by the floral and greeting card industries that encourages you to show affection in the form of a teddy bear and chocolates, when really, it shouldn’t take a contrived day on the calendar to tell someone you love them.

Either way, you’re probably on the hook for dinner and flowers.

But Valentine’s Day doesn’t have to be the same boring routine year after year. To help spice things up this year, make planning more efficient, and maybe even save you a few bucks, we rounded up a list of Chicago startups that can give you a major assist on Valentine’s Day this year.


Shopping for jewelry can be an uphill battle, especially if your special someone has really specific tastes. Luckily, Chicago startup Heirlume helps take some of the guesswork out of the experience. Heirlume helps you pick the perfect piece of jewelry with an algorithm that narrows down your choices based on a set of questions you answer about the gift recipient.  You answer questions like “What’s her favorite type of date night,” “What celebrity style does she relate to the most,” and “What’s her typical jewelry style,” and Heirlume gives you nine selections based on the responses. The company also has a Valentine collection to make shopping even easier.


Forget trekking over to Hallmark to find this year’s Valentine’s Day cards. Chicago-based Paperwoven lets you send real cards right from your phone. The Paperwoven app allows you to customize a message, add your actual signature with the touch screen, and send a Valentine’s Day card for $3.99. And it works with a network of artists so you’re sure to send an original, one-of-a-kind Valentine. And since it’s so easy, there’s no excuse not to send one to Mom, Grandma, and the rest of your family, too.


If your Valentine is a music lover, GigScout is the perfect app for finding great live music nearby. Whether it’s a show at the United Center or a one-man-bands at the dive bar down the street, GigScout lets you search for local music based on your location. The app shows you who’s playing in nearby venues, let’s you listen to a sample of the artist on Spotify, and you can even purchase tickets to some shows in the app. It’s a great option for an after dinner-activity or popping into a venue while you wait for your table.


If your Valentine’s Day plans have you driving around Chicago, finding parking could be an issue this Saturday. SpotHero, a Chicago-based startup that connects drivers’ mobile devices with parking garage operators with excess inventory, has a V-Day special to help you save some money on parking. Using promo code VDAY10, new SpotHero users will get $10 off their first parking spot on Feb. 14. It’s a nice option if you’re new to SpotHero and are looking to avoid expensive parking rates and Uber surge pricing.


For those doing a romantic Valentine’s Day at home this year, Foxtrot has the ingredients to help out your special evening. The delivery app offers a curated selection of food and beverages to bring the restaurant experience to your door. Order a bottle of wine, some cheese and crackers, and after-dinner sweets, which are all delivered in under an hour.


Before your big dinner Saturday night, how about giving your wife or girlfriend a spa day? Whittl lets you search local services like spas and salons, book an appointment, and pay right from your phone. Just tell your special someone when and where to show up and give her the gift of a relaxing Saturday morning.


For your Valentine’s Day flower needs, BloomNation has you covered. An online marketplace for hand-crafted, locally-delivered flowers, BloomNation helps you send beautiful floral arrangements to your special someone. While the startup is based in L.A., BloomNation was born out the the University of Chicago and placed third at the 2012 New Venture Challenge. Avoid 1800Flowers this year and opt for a truly original flower bouquet from this fast-growing startup.


If you’re doing some clothes shopping for your Valentine this year, SkyleSeek can help you find the right item. Similar to how Heirlume helps you shop for jewelry, StyleSeek uses an algorithm to find the perfect style for your significant other. Through its StyleGame, users answer a series of nine questions by choosing images that best represent the gift recipient’s style. Then, based on your responses, StyleSeek shows you a collection of items that match those looks. If shopping for clothes seems daunting, StyleSeek makes things a little easier.


Blitsy, an online marketplace for discount crafts supplies, can help you make a personal, one-of-a-kind gift for your Valentine. Instead of buying an expensive gift this year, spend your money and time making something truly original.

Creative Commons Image via m01229

Jim Dallke is a Senior Editor at American Inno. As part of the team that launched Chicago Inno in 2014, and Wisconsin Inno in 2018, Jim covers the ins and outs of Chicago and Wisconsin's tech and innovation scenes. He's always looking for a good story. Get in touch: