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CheekyChicago helps urban women rub elbows with like-minded people in the city's haute spots

I’m always looking for exciting events filled with fascinating people. There are a vast number of websites for any metropolitan city that inform you about all the events and restaurant openings, but it’s hard to sort which ones will have my kind of crowd in attendance (one of the first things I learned when I moved to Chicago is that Wrigleyville doesn't host what I'd consider "my kind of crowd").

I’ve been on the hunt for a site that will fulfill all my twenty-something requirements for quite some time and I stumbled upon a gold mine when I found CheekyChicago. The online lifestyle magazine describes itself as “a woman’s guide to the city” and upon further inspection it truly is. The site cranks out 30 articles a week covering everything from restaurants, nightlife and theater to music, fashion, fitness and culture. They also have a calendar homepage letting readers know about great events to check out each week.

I sat down with Editor-in-Cheek (Chief) Erica Levin to talk more about my new favorite site.

What makes up CheekyChicago?

There are three main parts of the magazine: our contributors write 30 articles every week on a number of topics and we have our homepage calendar that’s a compilation of the best things happening around the city that week.

We also have at least one event every month, whether it be our annual Cheeky’s Real People of Style fashion show we just wrapped up or a Women and Whiskey dinner at a restaurant. For our April event we’re hosting the unveiling of Bloomingdale’s new shoe department. We’re sending invitations out shortly.

The third aspect is our CheekyCard, which is our way to inspire readers to “live the cheeky way.” You sign up for the card and get perks—not deals like Groupon would offer—but perks. Free facials, bottle service, things like that just for having the card. Once you buy you get a comprehensive list of what perks we have for the year.



How did CheekyChicago come to be?

I was working at a high-end gym in the city when I met my business partner Jessica Zweig and we became fast friends. People always think we grew up together but we really just had an instant bond. We had a mutual love of Chicago and we were both passionate about food and drinks so we decided to try a new place each week.

We realized we both talk about food like we’re food critics and we considered starting a food blog—they we thought, why stop at food? Why not make it a fully woman-centric website? We went to a coffee shop across the street and began thinking up names. I love alliteration and CheekyChicago just came out of my mouth and we looked at each other and knew that was it.

We went home and bought up literally every single domain name that applied. We now own everything from CheekyDesMoines to CheekyLondon. Then we met with a lawyer, bought the LLC and set up everything we needed to operate before we even began building the site.



How did you know you had a hit on your hands?

We spent months designing the website and doing old-school marketing. We did email blasts, we put up fliers, we handed out papers at street fests and we had an email sign up page in place of a site.

Then we had a launch party for the site and 350 came without us paying a dime for marketing. That’s when we knew we had something. That’s also how we decided to start getting into the events side of the business too, and it’s served us very well.

What’s next for CheekyChicago?

Our plan is to expand. We’re launching CheekyAustin in the fall because it’s one of the most forward progressing cities in the U.S. right now and it’s definitely the trendsetter of the south.

Once we launch CheekyAustin we’ll know what it takes to open up in another market and we’ll be able to launch faster and more efficiently in other places.

We’re also working on a CheekyCard mobile app right now that will be geotagged it so you can walk out of work and get a notification reminding you that the lounge around the corner offers a complimentary glass of champagne for cardholders.



Right now we’re out fundraising and that's how we’re planning on moving forward with our planned projects. We’ve been pitching like crazy!


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Gabrielle Belavsky
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