CheekyChicago is an online lifestyle magazine for the women of Chicago. It is your social destination to the most exciting happenings in the city. Cheeky is your monthly event host, your weekly newsletter and your daily dose on all things fresh, feminine and fun. Cheeky gives back to our savvy community by offering fabulous perks and VIP status with our exclusive Cheeky Card Program.
In the girliest, most platonic terms: it was love at first sight. Or rather–love at first bite. The friendship between the two women really began with their mutual joy for going out in style, finding the latest, greatest restaurants, throwing down some wine and gabbing all night. The next day, they would re-live and critique every detail of the evening, only to start searching for the next great find. Whatever else lay hidden inside the nooks and crannies of Chicago, they were sure to uncover it.
They were struck–not only by this shared passion–but most importantly, by the openness and sincerity they each possessed that allowed such a fast friendship to transpire. This killer combo of ingenuity, open-heartedness and love for all things Chicago inspired the creation of CheekyChicago.com. Through this 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.
Simply put: Stephanie is a wine and spirits guru. A Social Media Strategist by day and the Drink Editor of Chicago Scene by night, she has her pulse on the latest liquor trends and could probably teach a course on the difference between Scotch and Whiskey.Read more
Born and raised in Chicago, Jennifer has been spreading her charitable wings since she was very little; wearing adult sized t-shirts down to her knees – volunteering at multiple fundraisers, walks and motorcycle rides held by The American Brain Tumor Association.Read more
Christine Hassler is a life coach, professional speaker and author specializing in the twenty-something life phase. Christine coaches individuals, organizations and corporations with the intention of empowering young professionals (Gen Y) and bridging generational gaps in the workplace. As a speaker, Christine delivers engaging and informative keynotes to conferences, colleges and businesses around the country.Read more
The Wine Guide comes to Cheeky with experience in a variety of journalistic endeavors. An award-winning producer, television anchor and magazine writer, she explores topics of interest with her own unique sense of humor. Now working in the wine industry, she will take you behind the scenes with exclusive interviews with winemakers, on the scene reports from the vineyards in Napa and Sonoma and share with you the latest trends in all things wine.Read more
Jennifer Boyer photographs and reviews artists live in concert with the added bonus of interviewing her favorite musicians, singers, songwriters and producers. She resides in New York City where she captures and witnesses great moments in live music. Jennifer’s obsession with music and concerts has turned two of her hobbies into dreams come true.Read more
Cheeky Kiki… where do we start with this Cheeky chick? Kiki is a reformed interior designer who started writing lifestyle pieces years ago only to fall into her dream job recently, as a food writer. Born and raised in the Chicago area, Kiki joins our Cheeky team as a dining and lifestyle expert.Read more
Sifting through brilliant silhouettes, romantic palettes and imaginative textures evokes a whimsical curiosity. Fashion has always excited Robin – whether piling on beaded necklaces and hosting makeover birthday parties in her 10’s or interviewing strangers about their undergarment style preferences for her college newspaper in her early 20’s.Read more
From as long as Erin can remember, her world has revolved around cooking a meal or enjoying one. She was lucky enough to learn her kitchen and entertaining skills from her classically trained mother, who showed her that some of the simplest recipes are the most delicious…. and best done while sharing a bottle of vino.Read more
Jenna is Cheeky’s new resident Pilates expert and Core Conditioning Champion! Founder and Director of Helios Center For Movement, Jenna has made it her mission to help Chicago get to the good stuff for posture, exercise and a lifestyle that shines from the inside out.Read more
Barbie Adler is a contributing columnist for Cheeky and president of Chicago’s top matchmaking firm Selective Search, an elite matchmaking firm that acts as a personal recruiter for the city’s most eligible bachelors. Selectively single women are invited to join for free by registering at selectivesearch.com.Read more
Karie Hill is a financial freedom coach, speaker and writer who believes financial freedom is one of the greatest gifts a woman can give herself. She teaches smart women how to build healthy, wealthy money habits, remove their financial barriers, and create the kind of life they really desire.Read more
Wendy Widom is the President of Families in the Loop, Chicago’s hippest hub for parents. When she’s not sipping on an iced Intelligentsia decaf latte (yes, even in winter), she is creating a whole new fun and feisty conversation amongst urban moms and dads who remember how cool they were before they had kids.Read more
A devoted foodie, Sam loves nothing more than recommending restaurants and bars whether in conversation with friends or in writing reviews. She also loves cooking, games, reading, taking in the breeze off Lake Michigan on a hot day and visiting her favorite animals at the Lincoln Park Zoo and Shedd Aquarium.Read more
A Cheeky girl makes a first impression without saying a word. That’s what Kari loves most about fashion; dressing to express the day’s mood and mission. Girly, preppy, hobo or rock ‘n’ roll, her style can’t be defined, always channeling inspiration from the runway and translating looks onto the “real way.” You can see more of Kari’s resourceful sense of style and read her quirky anecdotes on her personal blog, Style at a $teal.Read more
Lakesha Rose is a 6 year volunteer at Common Threads where she gives children’s cooking classes with an emphasis on creating enhanced cultural experiences that build social confidence. She is Honorary Chair of Almost Home Kids, a proud recipient of a 2013 Changing Worlds Humanitarian Award and annual “MC” at the Friends of Chicago Animal Care and Control Event. Lakesha Rose is also the founder of L.Rose Design a lifestyle design company and resides in Chicago with her husband, legendary Chicago Sports Broadcaster, Jim Rose and their dog Petey.Read more
Ashlee Piper, MSW, AADP is a former governmental strategist turned plant-based health and lifestyle expert. She is the owner of All Is Wellness, a boutique holistic health consultancy that assists busy individuals, families, restaurants, and workplaces in giving their food, routines, and lives a gorgeously green makeover.Read more
As Founder and CEO of PrettyQuick.com, Coco now makes it easy for on-the-go beauty enthusiasts to instantly find and book appointments at a curated network of salons and spas. When she’s not meeting with salon and spa owners, testing new services or interviewing the fabulous women who rely on her new app, she enjoys supporting the performing arts and serves on the Joffrey Ballet’s Board of Directors in Chicago.Read more
Nicole Regan quickly transformed to a city girl after graduating from the University of Iowa and moving to Chicago. Although a small town girl at heart, she hasn’t looked back since. She is the writer behind Cedar and Rush, a contributor to The Urbaness, co-founder of the women’s social club, Garnish and Glam, and a guest contributor to several other blogs.Read more
Chloe Cline is a writer, dating blogger and first date conniseuer. A former high school teacher, Chloe is no stranger to awkward situations, poor grammar and immature guys. In her hilarious blog, chloecline.com, she relays the trials (and infrequent triumphs) of the dating scene in Chicago.Read more
She is fun, fabulous and fierce. She is chic, intelligent and in-the-know. But most of all, the Cheeky chick is the kind of woman who embraces, admires, respects, smiles at and opens her heart to other fabulous chicks. Now THAT'S Cheeky, darling!