Cheeky ← Back to the Mugshots


When we are young we can meet our new bff by saying “Hi, I like your rollerblades. What’s your name?” And, without fail, they tell you their name and boom, you have a new friend.

What changes as we grow up? Especially when making female friendships? Why so serious?

Cheeky is the answer to that exact question!

“We believe in bringing women together in a supportive, entrepreneurial and social way,” says co-founder Jessica Zweig.  “I’m the best person I can be with the support of my girlfriends. I know other women feel the same and need that venue in their lives.” was built in 2008 when Erica Bethe Levin and Zweig bonded over their love of food and realization that there was an  opportunity to build an online community that encourage women to create new friendships and explore the city.  “We wanted to create a women’s guide to all things Chicago. So we built it.” said Levin.

Their favorite passion project within Cheeky is curating their fabulous events and the launch of the Cheeky Card – a VIP pass to Chicago!

(cut lines, free champagne!)

Through their website Jessica and Erica’s biggest and only hope is that the women across the Windy City embrace the cheekiness of Chicago but, most of all, embrace the cheekiness in themselves and each other. Now, that’s some mega gnar attitude that we should all get behind.

So, how can you make a babe’s day today? Compliment her blogging? Artwork? Her recent break-up? Let us know!