What is Cheeky?

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.

CheekyChicago is your ultimate key to the city.

Erica Bethe Levin


Erica Bethe Levin is the Co-Founder and Editor-in-Chief of CheekyChicago.com. She hails from that other coast known as the East. Her parents transplanted her from New York to West Palm Beach, Florida when she was just a small girl. Needless to say, after seven years in Chicago, her blood is still a bit thin and Florida-y. It must be from all the time she spent skipping debate practice to hang at the beach. After seventeen years of frolicking in the sun, Erica knew it was time to head to a less sandy and more windy climate; so she packed up and left for Northwestern University in Evanston, Illinois to become – none other than – a theatre major. This theatre major thing did not fly so well with the parents since she had to drop out of the Medill School of Journalism (and into the School of Communication) to pursue such theatrical practices as embodying a monkey at the zoo, running around in a unitard, playing a 20-year-old Lolita and squishing ground chuck in her hands as a raging Medea.  Read more

Featured Contributors


dr. debby herbenick

cheeky sexpert

Dr. Debby Herbenick is Associate Director of the Center for Sexual Health Promotion in the School of Health, Physical Education and Recreation at Indiana University (IU) where she is a sexuality researcher and educator.

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stephanie miller

cheeky on-the-town

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.

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debi lilly

cheeky martha

Debi Lilly is a nationally renowned event-planning expert based in Chicago. She is the founder and president of A Perfect Event – Chicago’s most successful special event company with a faithful (and famous) following, including Oprah Winfrey.

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jen hesser

cheeky does charity

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.

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jerrod melman

your cheeky guy

Jerrod Melman is a managing partner of Hub51, the dining, nightlife, and social establishment created by him and his brother, R.J., in Chicago’s River North neighborhood.

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marilyn moats kennedy

cheeky political grandmother

Speaker and Chicago career consultant, Marilyn Moats Kennedy owns MoatsKennedy, Inc. She does keynote speeches and runs corporate workshops on career planning, office politics and workforce diversity.

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showbiz shelly

showbiz cheeky

Showbiz Shelly is the entertainment reporter for B96 Radio. You can hear her four times every weekday morning reporting on the latest celebrity gossip.

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phyllis kingsland

rockstar realtor

Phyllis Kingsland is the Rockstar Realtor. Her nickname has little to do with her clients since Phyllis has worked with lots of Cheeky girls just like us!

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christine hassler, MA

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.

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the cheeky wine guide

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.

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rea frey

cheeky vegan

Rea Frey is a lover of food, words and relationships (possibly in that order). She is the author of two books, Power Vegan: Plant-Fueled Nutrition for Maximum Health and Fitness and The Cheat Sheet: A Clue-by-Clue Guide to Finding Out if He’s Unfaithful.

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jennifer boyer

cheeky concert connoisseur

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.

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kiki luthringshausen

cheeky kiki

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.

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oline eaton

cheeky bookie

If Jackie O and Elvis ever had a love child, this Cheeky chick would’ve been that kid!
A graduate of the University of Chicago with a Master’s degree in writing biography and a concentration in tabloids, Oline burst onto the literary scene in 1992…

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robin clement

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.

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sara r. fisher and caitlin murray giles

cheeky mamas

Sara R. Fisher and Caitlin Murray Giles wear many hats — moms, marketers, most likely to be first in line at the Nordstrom half-yearly sale — and they wear them all proudly!

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erin vondra

cheeky with a fork

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.

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jess piet

This Cheeky chick is as free-spirited as she is social media savvy, and (trust us) once you meet her, you won’t soon forget it. The jessundressed.com blogger who is “gettin’ real, NOT NAKED” is always reliably equipped with sparkling spunk and an on-the-dime will to explore.

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dr. payal adhikari

the cheeky doc

Payal is a pediatrician at Child and Adolescent Health Associates in the Gold Coast and loves all things healthy. Born and raised in Chicago, she moved to Singapore for high school and returned to her favorite Chi-city to attend Northwestern University.

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kristen mitchell

cheeky's film fatale

Born and raised in a suburb just outside of Chicago, Kristen is no stranger to this city’s Cheekiness. After a four-year retreat to rural Indiana, she graduated from DePauw University with a Bachelor of Arts in Creative Writing and Spanish.

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lisa payne

If this Cheeky girl could write and work out at the same time, she would! A self-proclaimed multi-tasker, Lisa began teaching fitness classes and personal training while getting her MFA in Writing from the School of the Art Institute of Chicago.

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katelyn finn

cheeky’s slave to the sartorial

Katelyn has had an interest in fashion ever since the ripe old age of four when her mother gave her a dress up box: consisting mainly of old bridesmaid dresses, eclectic 80’s pumps and some serious costume jewelry.

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jenna zaffino

cheeky core-espondent

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.

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Barbie Headshot

barbie adler

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.

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Karie Hill

karie hill

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.

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wendy widom

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.

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samantha nelson

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.

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kari radjewski

cheeky chic

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.

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tiffani swalley

cheeky comedienne

Tiffani Swalley watches entirely too much television. When this “Transplanted Southerner” pries herself away for the tube, you’ll find her writing press releases or performing around Chicago…or eating…or eating while doing both.

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Lakesha Rose

lakesha rose

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.

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susan brunstrum

cheeky design maven

Susan Brunstrum, founder of Sweet Peas Design, Inc., Libertyville, is proud to be Cheeky’s new interior design maven. She believes that “Cheeky” design means living the lifestyle of your dreams. She has been featured on LXTV, CLTV and many other ‘zines and blogs. Visit her at www.sweetpeas-inspired.com.

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ashlee final

ashlee piper

vegan for life

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.

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Coco Meers

coco meers

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.

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kit graham

Kit writes thekittchen.com where she shares original and practical recipes, and she just released her first cookbook, The Gourmet Grilled Cheese Cookbook.

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nicole regan

fashionably late

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.

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ashley gilday

cheeky self

Ashley Gilday, advocate of living well, eating well and paying it forward, is a Chicago native and one tenacious woman. Life hasn’t always been roses for Ashley. She overcame a life-threatening eating disorder in her early twenties and has since found her voice.

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chloe cline

drunk and dating

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.

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kaleigh glaza

chicago social

Entrenched in the social media world, Kaleigh moonlights as the Chicago editor of “Lux and Concord” in her free time. A Chicago native, Kaleigh is a die hard Cubs and Portillos fan, but also loves to travel to new places.

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ashley pettit

pettit living

Ashley W. Pettit infuses her passion and positive energy for healthy living into her comprehensive nutrition counseling, personalized training sessions and in-demand interval classes for individual clients and corporate companies alike.

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nina gardner

cheeky and balanced

Nina Gardner is a brand strategist, high heel enthusiast, gourmet chef wannabe, runner of moderate distances, yogi and writer who is living a life she loves in the city she loves.

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adriana aude

semi-green beauty queen

No one should have to choose between health and beauty. As a makeup artist, a model and a mother, Adriana understands the importance of putting her best face forward while not compromising her (or her children’s) well being.

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melanie rud chadwick

cosmetic connoisseur

Melanie Rud Chadwick is a beauty writer and expert, and… Read more

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