“She turned the skyline into a story and I will never look at it the same.”
Hillary, Founder & Guide
Hillary — entrepreneur, tour guide, teacher, improv comedian, and a member of the Chicago Tour Guide Professionals Association and Choose Chicago partner — is an energetic, engaging, and knowledgeable tour guide who is not only passionate about architecture and history, but also passionate about Chicago and what it has to offer visitors.
Some of the things that make her an excellent tour creator and guide include (click anywhere you see green font to learn more!):
A proven history of creating award-winning tours (#1-ranked architecture tour business out of hundreds on TripAdvisor, and named to TripAdvisor’s “Best of the Best” in 2023 and 2024 — an award given to the top 1% of ALL activities in the world!) not only for her own company, but also for one of the largest boat tour companies in Chicago. She single-handedly restructured, retrained, and revamped this boat company’s entire tour department, creating the path that led this company to be named the 2nd best traveler experience IN THE WORLD on TripAdvisor. Read more about that here.
More than a decade of experience as a tour guide in Chicago (boat tours, food-tasting tours, and her own company’s walking tours). Check out her video of “Five Common Myths on Chicago Architecture River Tours,” made after she got tired of the very common false stories told on many tours in Chicago, and wanting to set the record straight!
More than a decade of improv and sketch comedy training and performance experience, having performed with a team at the famous iO (formerly "ImprovOlympic") and other teams in Chicago, and coached improv comedy at the university level. She is quick-thinking and adaptable, and naturally uses humor as a way to engage guests on all her tours!
A Master’s degree in Comparative Literature and a Bachelor’s degree in French Language & Literature, together with years of experience teaching levels K-12 and university-level writing and language courses. She is highly skilled at communicating information in an interesting and graspable way.
Several years spent living abroad in France and Austria, two of her absolute favorite places. She taught English as a Second Language in Paris, where she lived in the stunning 7th arrondissement, and tutored Latin and English when living in Salzburg, where she lived down the street from the wonderful Augustiner Bräu (where she learned to love beer).
She is a proud polyglot, with English as her first/maternal language, Latin as her second, French as her third, Italian as her fourth, and German as her fifth. (Tucked away in a drawer of mementos are her medals from National Latin Exams.) Hillary loves learning any bits of language she can, and welcomes any opportunity to converse with guests in the languages she knows. Though her Italian may be rusty, if you need a Latinist, Hillary’s your gal. And c’mon: don’t we all need a Latinist?
More than a decade’s experience in professional editing and translation through her freelance business, The Finer Point. Besides being multilingual, Hillary is articulate and graceful in her communication style, and naturally conveys information in a very engaging way. She was even asked to have her tour translated into a number of languages for a major boat tour company in Chicago!
Hillary is an avid swing dancer, and enjoys cooking for friends and family. She is also the proud "mother" of three adorable cats, Bepps, Gimlet, and Jelly, plus her little old man cat, Abbers, who crossed the Rainbow Bridge in August 2021. Her grad school cat, Pingua (from the Latin word for “chubby”), who lived with Hillary’s parents, crossed over the Rainbow Bridge in February 2023. And because you are a super fan who has read all the way to the bottom of this bio, you can enjoy a secret cat album here!