Photo by Erol Ahmed on Unsplash, and messed up with letters by me.

Brian’s 2018, Mostly-Definitive Guide to Chicago Startup & Small Co.’s Holiday Gift Ideas

If you’re anything like me, when you’re not devouring any remaining leftovers, apologizing to relatives who you declared “insane” for political reasons, or ranting on Twitter, you’re probably starting to realize: “Oh man, I need to get Christmas gifts soon”. (Or any other non-Festivus Holiday that you and yours celebrate.)

Yeah, you know who you are. Don’t be ashamed, you still have time. Whatever you do, don’t descend into gift card madness — I’m here to help you find something that’s a good fit for everyone in your life (or at least those that aren’t dead-to-you yet). And if you want to support Chicago startups and small companies, then this article is the right place.

This list contains as many of the awesome up-and-coming Chicago companies that I could find or remember. My criteria for this list is pretty simple: based in Chicago, founded in the last decade, and relatively small & growing quickly (sorry HomeChef & Grubhub).

Fair warning: some of these are not really “gifts” in the traditional sense. You may just have to be that cool cousin or aunt who shares a website, app, or (god-forbid) retail location as your gift. In those situations, I’d humbly suggest an accompanying card with some cash in it (or perhaps some crypto on a USB stick, it’s cheap right now).

Outside of buying something from the list below, the single best way to help these companies is to tweet or share this article (or their websites, etc): awareness is almost as valuable as revenue to new companies.

Ok, enough already — here’s the list, in no particular order:

For the hungry (in other words, everyone):

These companies help you eat faster, easier, and better than you normally do. Ditch the Trader Joe’s certificates in favor of something from any of these companies.

  • Tovala — A unique all-in-one appliance and meal service that work in harmony to make home cooking effortless. This thing is amazing, seriously. (, @tovalafood)
  • Tock — Browse a collection of unique dining destinations and book a unique and delicious culinary experience. (, @tock)
  • Quevos — Nearly carb-free chips made from egg whites. I don’t understand how they do it, but I’m too busy eating them to care. (
  • Frönen — Frönen is a delicious, non-dairy ice cream made with simple ingredients. Not to be confused with the sausage king of Chicago. (
  • SWZLE — Eco-friendly, reusable straws. Probably for stockings or boozing quickly. (, @swzlestraws)
  • Foxtrot — Get craft beer, wine, spirits, fresh eats, gifts and everyday essentials delivered to your door in minutes. (, @foxtrotmarket)
  • Positive Pretzels — Amazing new pretzel company that just so happen to be f***ing delicious and coming soon to a store near you. (
  • Tea Squares — Put down the coffee and get your caffeine from your snacks, finally. (, @myteasquares)
  • DoubleGood — Gourmet popcorn that helps kids with special needs and adults who are too skinny. (, @doadoublegood)

For the curious, creative, and savvy:

Also works for that weird coworker who bought you a mini wreath for your cubicle.

  • Trala — Learning to play the violin has never been so easy or fun. (, @tralaapp)
  • BRD — The simple and secure way to get started with Bitcoin, Ethereum and other cryptocurrencies. (, @brdhq)
  • Lightstream — Help your 11yo nephew achieve fame from his gaming skillz with Lightstream — a powerful & intuitive live streaming studio in the browser. (, @lightstream)
  • Winston — Protect your family and browsing from spyware & identity theft. Coming soon but worth checking out. (, @winston_privacy)
  • Inventables — Help that retired uncle build an Etsy business with a truly amazing X-Carve machine. (, @inventables)
  • True Public — Discover what the rest of world thinks about the subjects you’re sure you’re right about. (, @truepublicapp)
  • Project Nande — Cool city and activity guides, ideal for recent arrivals to Chicago. (, @project_nande)
  • Speeko — Speech coaching app, perhaps for the recent college grad who still says “hella” in job interviews. (, @speekoapp)
  • RedlineVR — A new in-real-life way to experience virtual reality, so you can finally escape with a draft beer. (
  • Remote Year — It’s usually about this time of year I wish I could escape the upcoming winter wind barage. If someone in your life is looking to get away for a bit, check this one out. (, @remoteyear)
  • Mystery Tackle Box — A fun and affordable way to discover new fishing products every month. (, @mysterytacklebx)
  • DeskPass —Know someone looking for a change of scenery at work? Buy them a pass that lets them bounce around a few different locations. (, @deskpasshq)
  • Dabble — Local classes and experiences to learn something new or just have a fun saturday afternoon. (, @dabblehq)

For the parents (and pet parents):

No, I’m sorry, there is nothing that can bring back their “20’s lifestyle”, but there are some other ideas to give the recent parents in your life a little break.

  • Jiobit — Amazing & innovative wearable trackers for kids: Stay connected to your child (or pet), no matter the distance. (, @jiobit)
  • Mac and Mia — Stylish kids clothes handpicked by a personal stylist and delivered to your door. (, @macmiastyle)
  • Pearachute — Ditch the Netflix for kids and take the rugrats out to an activity or experience they’ll remember when they’re older and you’re senile. (, @pearachute)
  • Codeverse — Your kids are probably already programming, so you should encourage it more with coding classes & summer camps for children ages 6–12. (, @codeverse)
  • Figo - Simplified pet insurance for your furry loved ones. (, @figopet)
  • Digital Adventures — Chicago’s top-rated computer coding and engineering design classes, digital technology camps & technology-themed birthday parties for kids. (
  • Monica + Andy — Super soft and sweet clothes and blankets for babies. (, @monicaandykids)
  • Kids Science Labs — Only if you want your kids to be smart when they grow up, though. (, @kidssciencelabs)

For the fashionable & chic:

Or for that wanna-be instagram influencer in your family.

  • Curlmix — Awesome hair products for people with curly hair. This seems long overdue. (, @curlmix)
  • Stitch + Heart — Custom clothing that also fights cancer. Sounds pretty good to me. (
  • Luxury Garage Sale — Way better than rummaging through your Mom’s old stuff. (, @luxurygaragesale)
  • Bottlecode — Personalized skincare products for the men in your life that still use bar soap to wash their face. Gross, man, time to grow up. (, @yourbottlecode)
  • Cariset — Designer backpacks for carrying all the important stuff in your life on the go. (
  • ShopRunner — Amazon prime (ie 2-day shipping) for all your other shopping needs. Too bad you didn’t sign up yesterday, right? (, @shoprunner)
  • Oars & Alps — Natural skin care products that work without requiring a 2nd mortgage. (, @oarsandalps)
  • ZipFit Denim — Jeans that actually fit you, which is kind of a big deal this time of year. (, @zipfitdenim)
  • Equilibria — A great new farm-to-home women’s wellness company, offering some non-intoxicating CBD products to work, feel, and sleep better. (

For those in love (or like):

Even if you haven’t DTR’ed, some of these will still work for that special someone, or someone who has a special someone, or something like that.

  • Cameo — Book personalized video shoutouts from your favorite people for your favorite people. (, @bookcameo)
  • Brideside — Amazing Bridesmaid dresses + concierge service. Beat that, random bridal shop in a strip mall. (, @brideside)
  • Flowers for Dreams — Pretty simple: Send flowers, help a local charity. Do it already. (, @flowers4dreams)
  • Partyslate — Find an amazing venues and event professionals for your annoying cousins Wedding or Bar/Bat Mitzvah so you can get back to Instagram shopping. (, @partyslate)
  • Floracracy — Build your own personalized flower arrangements. (, @floracracy)

For the home or office:

Eat your heart out, Bed Bath N’ Beyond aficionados; your time is up.

  • Fixer — For that friend or relative who refuses to fix their broken toilet, hire them a handyman to help. (, @heyfixer)
  • Welltended — House plants that don’t suck and are delivered right to you. (, @welltendedlife)
  • The Minte — Hotel style housekeeping at home. Room service not included, unfortunately. (
  • MightyNest — Handpicked, non-toxic, eco-friendly and stylish products for home and family. (, @mightynest)
  • Bright Endeavors — Awesome, hand-made candles that support an amazing cause: Moms. Check them out. (, @brightendeavors)
  • HouseCraft — Use your phone’s camera and some augmented reality goodness to view 3D models anywhere in your world. (
  • Gramavox — Floating record players and vintage audio devices for the hipsters in your life who think vinyl sounds better than Spotify or whatever. (, @gramavox)
  • Ergo Impact — The best stool for your adjustable standing desk. (, @ergoimpact)
  • Interior Define — Custom-made sofas, beds, and chairs at attainable prices. (, @interiordefine)

For the fit & healthy (or those who aspire to be):

These companies will help you clean up your act and feel good while doing it. Generally not recommended in combination with a Portillos gift card…

For yourself:

About damn time, amirite?

  • Brew a pot of amazing, tailored-to-you coffee that you snagged from Javaya (, @getjavaya) and watch some terrible christmas movies.
  • Save some $$’s on your home insurance with Kin Insurance (, ideally to offset the rising property tax bills around here these days.
  • Get your car spic and span (especially after the rain, snow, and salt!) with Sparkl. (, @sparklnow)
  • When you’re out on the town running errands, make sure you’re saving money on parking with one or both of my favorite parking companies in chicago: Spothero ( or Parkwhiz (
  • Need some help at work? Host a short-term intern with help from Parker Dewey. Micro internships help college students learn and explore potential career paths, which is probably better than whatever else kids are doing these days in college.
  • Trying to reconcile your empty checking account and over-limit credit cards but can’t quite make out the figures or statements? You might want to check your eyes with Opternative (
  • Save up for next year’s Christmas with M1 Finance (, a free automated investment platform.

That’s it. Whew. Who knew Chicago had so many up and coming new companies? (Hint: I did). And I didn’t include any shameless plugs except for this one right here: We’re building Draftbit (, @draftbit) to make building mobile apps as easy as Wix and Squarespace make building websites. Check it out.

P.S. — If I missed a Chicago startup or company you’re running (or are a fan of), please hit me up. This is officially a one-time exemption to my “don’t @ me, bro” rule for Twitter, so use it wisely. Cool? Also good to let me know if I said something wrong, offensive, or stupid. Can’t guarantee any improvement there, though, that’s someone else’s department.

Go do well and be well. Happy holidays.

A big thank you to Tim Grace and Rebecca Sholiton for helping me assemble this list!



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