The 24 Coolest Small Businesses In Chicago


This is the part of the “Small Business Roundup,” focusing on the coolest small businesses around the country. “Small Business Roundup” is sponsored by UPS. Read more in the series »

Chicago’s got it all
: friendly people, tons to do, and a plethora of awesome restaurants, shops, and businesses.
We’ve found the 24 coolest small businesses in the Windy City.

There’s a 1930s-style Chinese teahouse, a secret agent store, and an events firm with an indoor treehouse and zipline.

ACME Hotel Company

15 East Ohio Street

What it is: A high-tech alternative boutique hotel.

Why it's cool: ACME is a hotel that caters to a very hip crowd. Not only do they offer tech-savvy hookups like lightning fast Wi-Fi and big screen LED TVs in every room, but they're decked out in a subtle alt-rock theme, from the classic record albums lining the walls of their elevators to their own killer Spotify playlist.

bethie b.


What it is: A company that specialises in hand-painted and custom-made pillows.

Why it's cool: The founders of bethie b. are Meg Goldberg and Beth Barron, a mother-daughter 'pillow-creating design team' with an eye for the unique, creative, and handmade. In addition to their crafty pillows, the bethie b. team also buys and sells recycled interiors, furnishings, and art.

Belmont Barbershop

2328 W. Belmont Avenue

What it is: A barbershop straight out of the history books.

Why it's cool: Belmont Barbershop is known for creating classic men's looks, particularly in their trendy, vintage haircuts like the pompadour and the high-and-tight. Customers can browse comic books while waiting for their cuts.

The Boring Store

1331 N. Milwaukee Avenue

What it is: A store that sells everything you need to be a secret agent.

Why it's cool: 'We are purveyors of all things boring... We are certainly NOT a secret agent supply store,' claims the Boring Store website.

Contrary to the name, the Boring Store is anything but. Along with fake mustaches and high-tech surveillance equipment, the Boring Store is actually a front to 826CHI, a non-profit writing and tutoring center for local students.


4 East Ohio, Studio 12

What it is: A personal shopping service right in your own home.

Why it's cool: CakeStyle helps customers decide what to wear. The CakeStylists work with clients' different budgets, office dress codes, and preferred styles and designers. Then they mail each client a box of custom-tailored looks, with a video that explains each outfit. Clients keep what they love and return what they don't.


1047 W. Madison Avenue

What it is: An Irish ice cream parlor.

Why it's cool: This ice cream parlor makes flavours in all things Irish -- think Bailey's, Guinness, Irish Mint Chip, and Jameson.

And don't forget their decadent, goodies-packed ice cream sundaes, like the Hair of the Dog sundae, which includes a scoop each of Bailey's, Guinness, and Jameson ice creams. The whole thing is drizzled with chocolate syrup, topped with whipped cream and a cherry, and sprinkled with Cadbury's flaked chocolate.

Flowers For Dreams

Online, in Chicago and Boston

What it is: A florist that donates a backpack full of school supplies to a student in need for every bouquet purchased.

Why it's cool: The company's flowers are sourced organically, grown sustainably, and delivered locally in and around Boston and Chicago. Arrangements are made to order, so no flowers are wasted unnecessarily. In its first year, F4D donated more than 2,000 backpacks, filled with notebooks, folders, pens, and other supplies, to more than 2,000 students in need.


Online, and at various retailers

What it is: A curated online marketplace for local and vintage furniture.

Why it's cool: Furnishly makes the process of finding and buying great furniture from individuals and a variety of partner stores easier and more reliable.

Where Craigslist can be disappointing or even unsafe, Furnishly goes through and approves each listing to make sure the quality and condition of each piece of furniture matches their standards, and the standards of customers.

Heritage Bicycles General Store

2959 N. Lincoln Avenue

What it is: A combination custom bike shop and coffee house.

Why it's cool: Heritage Bicycles designs and builds custom-made bikes (mostly commuters) and sells awesome bike accessories and bike-themed items, like jewelry made out of bike parts. They also sell -- surprise! -- coffee and snacks. The shop has become a popular local hangout for bike enthusiasts and entrepreneurs alike, who take advantage of free Wi-Fi as they enjoy a warm beverage and tasty snack.

Hotel Lincoln

1816 North Clark Street

What it is: A historic yet fresh new hotel.

Why it's cool: Located in an old 1920s-era building in Chicago's North Side, the Hotel Lincoln has a vintage vibe yet feels thoroughly modern. The guest rooms are eclectic, featuring modern furnishings and unique artworks by local artists, and there are two on-site restaurants: the J. Parker and Perennial Vivant.

JoJo & Sofia


What it is: A company that makes handmade, vintage-style accessories.

Why it's cool: Sarah Sebastian, founder of JoJo & Sofia, named the business after her two grandmothers. JoJo & Sofia has been making vintage and steam punk-style jewelry for over a year. Their wares, which include tie clips and cuff links, are designed mainly for men, but women can find funky necklaces and bracelets in the same eclectic style.

Landmark Century Centre Cinema

2828 N. Clark Street

What it is: An indie and foreign film theatre with gourmet movie snacks.

Why it's cool: Landmark Century Centre Cinema screens hard-to-find indie movies and foreign films. Moviegoers can watch the films in stadium-sized screening rooms while munching on gourmet snacks like warm vegan cookies or popcorn seasoned with custom flavours from the popcorn seasoning bar.

Madame Zuzu's

Billy Corgan welcomes guests to Madame Zuzu's.

582 Roger Williams Ave., Highland Park

What it is: A 1930s-style Chinese tea house.

Why it's cool: Zuzu's was started in the fall of 2012 by Billy Corgan, frontman for the Smashing Pumpkins. There are dozens of varieties of tea on offer, and interesting events almost every night, like open mic nights, poetry slams, and hypnosis workshops.


Online, based in Chicago

What it is: An online marketplace where you can request anything to be made by people who know how.

Why it's cool: Think of it as 'the eBay for everything that doesn't yet exist.' Makers can log in and list the things they can make for you, while Requesters can request items the Makers promote. Requesters don't have to limit themselves to items listed on the site, either. They can take anything they see on Facebook, Pinterest, or other sites and request that they be made by a Maker on MakeItFor.Us.

Red Frog Events

320 West Ohio, 1W

What it is: An adventure-driven events management company.

Why it's cool: Red Frog produces, advertises, and markets adrenaline-inducing events. In 2007 its founder, Joe Reynolds, was inspired by the TV show 'The Amazing Race' and decided to organise his own version in Chicago, which he called the Great Urban Race. It drew so many followers that Reynolds realised he could make a business out of it, and now Red Frog also produces the Warrior Dash, the Illuminite Run, and many other events, earning tens of millions in revenue, according to the Chicago Tribune.

Red Frog also prizes its relaxed workplace culture and its incredible obstacle course-like office. The office, which employees call 'Camp Red Frog,' comes complete with an indoor treehouse and zip line.


2163 N. Clybourn Avenue

What it is: A shop that uses geometric body scans to build your perfect bike.

Why it's cool: roll: knows the importance of fit on a bike, which is why they offer free complete body geometry scans to make sure every bike fits the customer to a T. The shop also hosts weekly group rides around Chicago, and promotes cyclist engagement with local and national causes like the Tour de Cure.

Salvage One

1840 W. Hubbard Street

What it is: A store that sells historic items salvaged from buildings that are about to be demolished.

Why it's cool: Salvage One rescues antiques from buildings that are about to be demolished, fixes them up, and resells them to customers who will appreciate them. They sell everything from mid-century tables and chairs to 1960s-era floor lamps to antique brass door knobs. In addition to selling what they salvage, they also rent out some of the items for weddings, private parties, and film and photo shoots where they can be admired and appreciated.


3011 N. Broadway Street and online

What it is: A funky T-shirt shop.

Why it's cool: Threadless sells unique witty, ironic, and pop-culture-referencing T-shirts. Artists around the world submit their T-shirt designs on the Threadless website, which get scored by customers who want to see the designs printed. Though they're best-known for their T-shirts, the store also prints designs on other apparel, iPhone cases, home accessories, and backpacks.

The Violet Hour

1520 N. Damen Avenue

What it is: The 'first handcrafted artisanal cocktail lounge' in Chicago.

Why it's cool: The Violet Hour is an elegant and sultry cocktail lounge named for a T.S. Eliot poem. With its luxurious draped plum-coloured curtains and its high chandeliers, the bar feels exotic and upscale. The drinks are artfully-crafted with high-quality ingredients. Take, for example, the Juliet and Romeo (gin, mint, cucumber, and rose water) or the Daisy 17
(whiskey, lemon, grenadine, and orange bitters).

What the Traveller Saw

1508 E. 55th Street

What it is: An international gift shop and travel tour service.

Why it's cool: World traveller Laurel Stradford was living and working overseas when she wrote her book, What the Traveller Saw. Her Hyde Park shop, which sells everything from luggage and travel accessories to pottery, tea, and vases, has the same name. Stradford also offers small, annual guided group tours to a different location each year so her customers can also see what she -- the traveller -- saw.

Now see what's going on in another American city.

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