Hillary, Founder & Main Guide

Hillary -- a member of the Chicago Tour Guide Professionals Association -- is an energetic, entertaining, and knowledgeable architecture tour guide who is not only passionate about architecture, but also passionate about Chicago and what it has to offer visitors.  Some of the things that make her an excellent tour guide include (click anywhere you see light green font to learn more!):

  •  A background in Comparative Literature and languages, and 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. 
  • Nine years of experience in professional editing and translation through her freelance business, The Finer Point. She is articulate, 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!
  • Eight years of experience as a tour guide in Chicago (both on architecture boat tours and food-tasting tours).  She is completely comfortable leading a group of people, maintaining the interest and pace of the group without losing sight of the individuals.
  • More than a decade of improv comedy training and performance experience, having performed with a team at the famous iO (formerly "ImprovOlympic").  She is quick-thinking, adaptable, funny, and great company for exploring Chicago!

When not showing people around this gorgeous city on her new architecture walking tours, Hillary is an avid swing dancer, and enjoys cooking for friends and family.  She is also the proud "mother" of two adorable cats, Beppe and Gimlet. (Because she is a proud cat lady, and because you've read this far, she'd like to share this secret photo album with you here.)


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Rebekah, Holiday Lights & Sights Guide

Rebekah is a Chicago transplant who had planned on spending a few weeks in Chicago one summer, and never left!  An avid jazz enthusiast and singer, she chose to remain in Chicago due to her love of the city and passion for its arts & music scene.  Born on an Air Force Base in Florida, and raised in small-town Missouri, she decided to move to Chicago after attending college in Fayette, MO, and completely fell in love with the historically rich music scene of Chicago.  When she's not showing people around the city or singing at places like the Green Mill, you can find her practicing yoga, waiting tables, and taking every chance she gets to meet and interact with incredible people from all around the world, people who've come from elsewhere and who fall in love with Chicago like she did.  "I love the progressive atmosphere of the city, the beauty in walking down the Lake Shore Trail, and the sound of the L in the night."