Meet Wendy


Wendy knows so much about Chicago and her love for the city shines through in this tour. We learned so much about the history of the city’s growth and the buildings as well as the colorful characters and incidents along the way.  ~Marcia, The Roaring 20s: Art Deco & Decadence Walking Tour

This is my second time on Wendy’s superlative tour. This time I brought along my sister from New York and thanks to Wendy she has fallen in love with Chicago (at least the Mag Mile!). This is a wonderful way to spend the morning with a knowledgeable, engaging and very funny Chicagoan and brilliant docent. ~Annie, Mag Mile in the Morning tour

Wendy’s tour is awesome. She combines a wealth of knowledge and energy with interactive gems from her iPad to make the tour REALLY come alive. She is remarkable!  ~Mag Mile tour guest

This was just a wonderful 2 hour tour, very in-depth with Wendy doing lots of research and showing pictures of by-gone days on her iPad as you walk. Very easy to walk and real quality time spent viewing buildings and the history behind one of Chicago’s most famous avenues. She really goes above and beyond and gives a very entertaining and yet historically detailed tour. You also go into some wonderful historic as well as modern buildings.  My husband and I truly enjoyed it.  ~Diane

Welcome!  I started WendyCity in 2014 in order to give top-quality, small group, personal tours of Chicago.  Those efforts have since developed into much more (podcast, Milwaukee tours).

Here’s a bit of my back story:

1) I’ve always liked cities.  Wauwatosa, a close suburb of Milwaukee, Wisconsin is my lovely hometown and on one of the few days I dared to skip out of high school, I took the bus to downtown Milwaukee.  For the city buzz.  And then there was always the ultimate thrill of going 90 miles south to Chicago!  I couldn’t wait for the first glimpse of that skyline.  I still feel that way.

Me (center) with my sisters – early 1970s

2) I’ve paid attention to buildings all my life but didn’t know anything about architecture.  As a child in 1960s Milwaukee, I remember being fascinated by (what I now know as) Modern architecture: the War Memorial at the lakefront, the County Zoo buildings, a few Catholic churches, the glassy Marine Bank downtown, Milwaukee’s Public Museum.   In the early 80s, I lived for a few years in Burlington, WI, a town filled with grand Victorian houses set on spacious, hilly lots.  I walked my baby son and dog right past those beauties, admiring, but not knowing a darn thing about them.


Eero Saarinen’s 1957 Milwaukee War Memorial Center

3) Architecture finally, seriously, got my attention in the 1990s.  I woke up to the fact that I really, really liked looking at and learning about great buildings.  And I simply liked being near them.

4) Two developments at my parish church, St. Sebastian’s in Milwaukee, gave me two great opportunities.  The person who gave a ‘behind the scenes’ tour of the church left and the person who handled the church archives could no longer handle them.  I volunteered to do both.  I began to give a historical-architecture tour of the richly designed 1920s church for adults and the school kids – while also explaining some of the mysteries involved.  I dug into the archives and created a history slide show-talk that I presented often to many different groups.


Giving St. Sebastian kids a tour of the church

5) Having gotten a taste of being a tour guide, I wanted more.  I completed training to be a Historic Milwaukee tour guide and eventually led three different downtown walking tours.  I had moved downtown, too, and was now a member of the Cathedral of St. John, which, happily, provided many regular tours of its sanctuary.  I was soon one of their busiest tour guides, especially once the cathedral opened after a major (and a little controversial) remodeling.

6) Up to this point, being a tour guide was a volunteer labor of love.  But I went on a choir tour to Europe (singing at the Vatican, in Venice, in Vienna…) and it rocked my world.  The musical experience was unforgettable, but crucially: I saw all of these European tour guides making a living.  I was determined: I was going to do the same.

Here's to you!

Here’s to you!

7) I completed my BA in Communication at Alverno College-Milwaukee and it was on to graduate school to pursue my goal: being a European tour guide for the PBS personality I so admired: Rick Steves.   I decided to study Art History (European, of course) and Italian – and to take a Rick Steves tour.  Things were going along fine: I was specializing in Bernini and studied in Italy for a semester.  I took that Rick Steves tour – of Florence and Siena – and the tour guide let me lead a little bit of it.  Toward the end of grad school, I was indeed hired by Rick Steves and worked one season in Europe as an assistant tour guide.

In Paris

8) But a couple of things changed my course.  I had been working at Ashland, The Henry Clay Estate in Lexington, KY and was absolutely devoted to it.   Further, as a teaching assistant in grad school, I happened to catch another professor begin her class after ours… and I stopped and listened, transfixed.    This phenomenal professor was Wallis Miller and the class was 20th Century Architecture.  I immediately made arrangements to get into her class.  I made sure that Architecture would still fit under the Art History program I was already deeply into.


At Ashland, The Henry Clay Estate

9) I left Bernini and European tour guiding behind and instead focused on the history of Ashland as a public-private place (and fascinating architectural hybrid), took on museum studies and architectural history courses.

10) Through my thesis about – and work at – Ashland, I discovered my life’s calling: interpreting history and architecture.  It’s what I love and it’s what I do.

11) In 2009 I brought my life’s work to Chicago and enjoyed interpreting the city’s history and architecture for thousands of people.  In 2019 I moved back to my hometown of Milwaukee to be near my family.   I’ve started a podcast of shared stories between Milwaukee and Chicago.  WendyCity should perhaps be ‘Cities.’

Leading a private group on my Art Deco tour

12)  Connect with me on Twitter or Instagram or via email:

THANKS for visiting WendyCity.

Leading an architecture tour on the Chicago River

Comments from WendyCity’s stellar tour guests:

Great tour guide– very informative and fun!!  ~Kathy, Mag Mile in the Morning tour

Extremely informative, more intimate, smaller tour with opportunity for lots of questions on many subjects. Wendy is personable and enthusiastic. Knows her subject matter well. Would highly recommend her to anyone visiting the city. ~Mag Mile in the Morning tour guest

Wendy is refreshingly down to earth; she is extremely knowledgeable about all things “Chicago.” The tour was lots of fun and incredibly interesting. Wendy enhanced the walking/talking parts by sharing images and even music (!) on her iPad. I highly recommend this informative and very enjoyable Mag Mile tour! ~Annie M., Mag Mile in the Morning

We had a wonderful experience. Wendy was an awesome tour guide. Very professional and informative. We were lucky to have a private tour with Wendy. Highly recommend this event.  ~Dudley, Mag Mile in the Morning

An enjoyable, educational, & fun tour. We went on a rainy morning, which didn’t slow any of us down. If anything, it got us closer to the design & decorations of the arches & overhangs of the interesting & iconic buildings of the Magnificent Mile. And the rain eventually stopped, so we still got plenty of exterior views & info. Wendy knows her stuff, very informative, and sociable & nice (all key traits for a great tour guide). We would definitely go again, and you should too. Thank You Wendy!  ~Laura, Mag Mile in the Morning

Wendy was so fun and engaging! I’m a huge fan of Art Deco and I learned a lot about the style and history with how it relates to Chicago’s culture, from fashion to architecture. Wendy picked interesting and varied locations around the loop that showcased various aspects of the style. Great use of technology by showing how various parts of the city used to look or videos that illustrated particular venues and events. Can’t wait to go on another tour!  ~Sam, Roaring 20s: Art Deco & Decadence

Wendy’s 1960’s Night Life tour is a fun and enjoyable way to learn more about Chicago’s fascinating past and present. Wendy brings the 1960’s to life as you walk and talk about Hugh Hefner and the “bunnies” or the “royal” Palmers and their mark on Chicago’s past and future. Wendy has a lot of interesting information to share and clearly loves Chicago and is excited to share it with her tour guests. We loved that her tour ended at the famous Pump Room with an opportunity to imbibe in some food and beverages. Great way to end a delightful tour. ~Cathy, 1960s Nightlife in the Gold Coast

Wendy was so informative and I felt that she really loves giving these tours. Very friendly, answered all questions and even gave us a wonderful tip for where to go eat afterwards!  ~Corissa, Mag Mile in The Morning tour

Our tour guide, Wendy was charming, knowledgeable and made the tour wonderful for both adults and older children.  Beautiful house, excellent guide, worth seeing.  ~Guest at Glessner House Museum

Wendy who gives this tour is very personable, very knowledgeable and very passionate about the topic, i.e., the Chicago theater and nightlife scene of the 1950s. She gives a comprehensive history and explains the architecture of the theaters, nightclubs and performers that were popular and shows photos to provide visuals along with the narrative. We ended the tour having drinks and snacks at the historic Palmer House while Wendy gave us an in-depth background of the Palmer family that had such a profound influence on the city, which continues to this day. I would recommend this tour to anyone who has an affection for that Sinatra-Monroe-Presley period in U.S. history, even if you weren’t born yet. An unusual and pleasant way to spend an evening.  ~Roberta, 1950s Nightlife in the Loop

Thank you for a great tour. The group was so happy with you.  ~Private group from the UK, custom tour

Very fun and interesting tour. Great way to learn more about Chicago’s fascinating past. ~Cathy, 1960s Nightlife in the Gold Coast

Thank you for such an amazing tour. Actually, it didn’t feel like an excursion, it was like being out with friends…You have an extraordinary history of Chicago and such an engaging spirit.  ~Jayne, 1950s Nightlife in the Loop

Awesome Tour! We took the Magnificent Mile Tour…..amazing! Wendy provided so much information we never would have known about. Wendy was well prepared, professional, and definitely well informed. Highly recommend the tour!  ~Toby, Mag Mile in the Morning

If you’re a history buff or even if you just like good food and drinks, do yourself a favor and book a tour with Wendy!  My coworker had done a tour with her before and I’m so glad she suggested it.  Wendy changed her schedule around to do a private tour with us of the 1950’s Chicago.  She is a wealth of knowledge with a clear love of the subject matter and I thoroughly enjoyed every minute of it.  The pictures and videos on her iPad were the perfect way to help us travel back in time.  Wendy’s warm, friendly personality drew me right in and I felt like I was having a night out with a good friend.  Everything we ate and drank at the Berghoff and Palmer House Bar restaurants was outstanding, and it was clear that Wendy makes friends wherever she goes.  I hear she gives great restaurant suggestions aside from tour stops, too.  Thanks again, Wendy!  You and the tour were an absolute delight. ~Ann, 1950s Nightlife in the Loop

Very thorough and up-to-date information on the Mag Mile and Chicago as a whole. Good pace of talking and walking, balancing the historical with the anecdotal.  ~Karen, Mag Mile in the Morning

My husband and I as well as a friend had the pleasure to take Wendy’s 1950s Nightlife in the Loop tour this past week. Despite the rain Wendy maintains a sunny disposition and seems to have a genuine interest in learning about her guests. She is also open about her journey to how she started this tour company. Her knowledge and enthusiasm is maintained throughout the entire tour. The two stops during this tour were fascinating. My fav part is how she ends her tour.. A fun game if you will.  Two things strictly coming from our recommendations and not at all from Wendy herself. First, offer to buy her a drink she may or may not accept but with all the talking and hosting a cocktail is well earned though I know she wouldn’t be offended if you didn’t . Also if you’ve never been on a city tour.. It’s always customary to tip the guide at the end of a tour. She is worth every penny and more. So much so that this is the only tour (in addition to the river tours) you’ll need to take bc we learned so much and much of the same info was repeated on other tours, yet this is the most affordable.  ~Sally, 1950s Nightlife in the Loop

We took the Mag Mile tour and after reading reviews and Wendy’s resume, we expected good things. WOW!  Best tour ever. Wendy’s knowledge of and love for Chicago comes out in a tour that is entertaining and detailed, including historical photos and even an historic recording loaded onto her iPad. A great tour with a personal touch.  ~Barbara, Mag Mile in the Morning

Wendy was great!  ~Diane, Explore Marshall Field’s

Wendy guided us on a fun & offbeat journey through the the colorful history of famed Chicago retail emporium, Marshall Field’s. She highlighted the holiday traditions that generations of Chicagoans have come to love, and shared fascinating stories about the men and women who started a retail revolution that swept the globe! Add the tasty Frango mints, the architectural gems ‘hiding in plain sight” and Wendy’s thoughtful selection of vintage media and we had a tremendously satisfying experience! I recommend the tour for visitors and locals alike!  ~Jennifer, Explore Marshall Field’s

Never had a better tour.  Wendy knows so much about Chicago and her love for the city shines through in this tour. We learned so much about the history of the city’s growth and the buildings as well as the colorful characters and incidents along the way.  ~Marcia, Mag Mile in the Morning

My husband and I took two of Wendy’s tours and we feel so fortunate to have found her touring company.  We were taking our first visit to Chicago and were concerned about being overwhelmed with the city and all of its History.  I wanted to make the most of our time and see as much as possible.   We found Wendy on tripadvisor and  we took two tours with her first her Retro night tour which started us off at Argo Tea Cafe which had some history of its own where we were given  a special treat from days gone by.   Wendy showed us pictures and video and took us on a nostalgia night out in Chicago, We ended up at the Beautiful Palmer Hotel and learned the history of not only of the Hotel but of the Palmer Family.   The next day we took her two hour walking architectural tour of the Magnificent Mile, WOW, Wendy has so much knowledge of Chicago architecture and so excited to share it with us. again showed pictures of what it was like in the early days which enhanced tour Chicago  experience, the Chicago Tribune Building is amazing to say nothing of the beautiful church that is serene and spectacular right in the heart of the mile.    We ended our tour at the famous Drake Hotel which was worth our time all on its own.  It was like walking with a very knowledgeable friend thru the streets of Chicago, Wendy  really made Chicago come alive for us.  If we visit again we will defiantly take additional tours with Wendy.  ~Sandi, 1950s Nightlife in the Loop, Mag Mile in the Morning

Wendy is an excellent tour guide. I highly recommend her to anyone looking for a fun and informative insight into Chicago history and architecture. ~Michelle, Mag Mile in the Morning

Wendy was great! She obviously is passionate about the city and sharing it’s history.  ~Ann, Mag Mile in the Morning

Wendy did a great job explaining the history and architectural buildings in Chicago. She was very professional, yet very personal. She gave us time to look around and explained things we would have never noticed, as well as tidbits of insider scoop! She communicated via text message to remind us of tour, location to meet, update her arrival time due to an emergency on her train. We always knew the status of our tour. We felt very cared for! She gave us great recommendations of places to go after we finished the tour. I would definitely recommend WendyCity tours to anyone visiting Chicago. I wish we would’ve had time to do more of the tours that she offered.  ~Laura, Mag Mile in the Morning

Wendy was very friendly and informative. Learned a lot about my favorite store and it brought back many good memories. I would recommend this to anyone who has a love of Chicago and a love for the “old” Marshall Fields.  ~Lenore, Explore Marshall Field’s

I have lived in Chicago my entire life (36 years) and I learned so many new things and saw amazing, beautiful places I never knew existed! When you live somewhere you don’t always take advantage of all it has to offer and you go about your daily activities missing all the beauty around you. Wendy is so knowledgeable and passionate and showed me all there is I am missing. I can’t wait for the next tour with Wendy City Chicago!  ~Sarah, 1950s Nightlife in the Loop

Wendy was very knowledgeable and presented the tour in a very friendly and fun manner.  ~Patricia, Explore Marshall Field’s

Wendy did her homework on the Fields Christmas tour. She put a lot into showing us so many details with pictures ,dialogue and a video. Wendy took us through the different buildings of Marshall Fields. She pointed out historic fixtures, ceilings and notable shoppers from long ago to the present. Very interesting and most enjoyable tour. Thank you Wendy.  ~Mary, Explore Marshall Field’s

My husband and I toured with Wendy one cold Saturday morning in January and it was a perfect tour in every way. Wendy is one of the most knowledgeable guides and she makes history come alive with her iPad. She was easy to listen to and she had great stories about the history of many buildings that we locals have walked past a thousand times. I was so thankful to have given this tour to my husband as a Christmas gift. We both loved it! It is perfect for locals and out of towners alike. Enjoy! ~Barb, Mag Mile tour

Top Shelf.  Wendy really knows her tour information. And she has a lot of fun doing it. I enjoyed spending the morning learning more about Chicago and all the cool buildings. Thanks so much.  ~Andy, Mag Mile in the Morning

Great tour guide– very informative and fun!!   ~Mag Mile in the Morning tour guest

Wendy was so informative and I felt that she really loves giving these tours. Very friendly, answered all questions and even gave us a wonderful tip for where to go eat afterwards!  – Mag Mile in the Morning tour guest

I toured the Mag Mile with Wendy … Wendy was FANTASTIC!  She is friendly, engaging, informative and clearly loves Architecture. I gained new knowledge, which I have been sharing, and completely the enjoyed the tour.  Take this tour, or any tour Wendy offers, as she is perfect for this profession! ~Jayne, Mag Mile in the Morning

Wendy was really interesting and had all kinds of interesting stories…   ~Bernadette, 1950s Nightlife in the Loop

She is a wonderful host, full of knowledge and very personable. She made everyone in our group feel comfortable.  ~Lisa, 1950s Nightlife in the Loop

Wendy was an excellent guide–enthusiastic and well-informed. She struck just the right balance, making the evening seem like a fun outing with an extremely knowledgeable and sociable friend, rather than a standard tour. She had also gathered a collection of relevant historic images that she shared with us on her I-Pad–a very good way to enrich the visit. ~Ginny, 1950s Nightlife in the Loop

Wendy is a wonderful storyteller, making history come alive. ~Carol, 1950s Nightlife in the Loop

Walking with Wendy is WONDERFUL !! I just took my second tour with Wendy and have booked a private tour for my family next month. Wendy makes the city come alive with her knowledge and her shear love for the city. Her engaging presentations and enthusiastic attitude make her a stand-out guide. Her tours are well paced and full of interesting information about Chicago’s history, architecture, and important characters that made this city great. If you are looking for an experience that is both entertaining and educational – take a tour with Wendy City !! ~Michelle, Mag Mile in the Morning

If you want to get to know Chicago better, Wendy is your girl! What a great way to bring the city you love to live with great stories and visuals of the places and people that made Chicago what it is today! Wendy had us engaged throughout the tour with her knowledge and enthusiasm about the city.  Next time you are in the city take a Wendy City tour, you’ll love the experience. – A.T., Mag Mile in the Morning

Once again had a wonderful time, I loved the pictures making it much easier to really visualize the past. I also love being able to stop in venues along the way to get a chance to taste and drink the best the city has to offer. Wendy’s groups always have interesting guests too. ~Bernadette, 1950s Nightlife in the Loop

Wendy is awesome! She held a personal tour with us! Wendy knows so much and she is so much fun to be around! She has more insight on Chicago than most other tour guides. Don’t miss out! ~Lynn, Mag Mile in the Morning

Had a fantastic time on this tour last weekend. I went with my partner and was a little worried about a 7:30 am walking tour but it turned out to be amazing. We learned so much from Wendy and she made the whole thing very enjoyable. I would recommend this to anyone currently living in Chicago, or any out of town guests who are looking for a fun morning adventure. Great way to start your day and so much fun information. ~Andrew, Mag Mile in the Morning

Wendy was FABULOUS! My fiance and I got to enjoy a pleasant walk through the city while learning about Chicago Nightlife in the ’40s and ’50s. Wendy was very energetic and informative. You can tell she has a passion for history and she doesn’t just tell “stories”. She makes sure she has the facts. It was very interactive with an open dialogue for questions. I loved that we got to have something to drink at Berghoff’s and then dessert at the Palmer house – so fun! I would recommend this tour in a heartbeat.  ~Samantha, 1950s Nightlife in the Loop

Wendy is passionate about Chicago and Chicago’s legendary architecture, and her tours bring you right into that passion. The Loop is an exciting place to be and every block is festooned with great art and architecture. Walk these streets with Wendy and she will take you into the heart and soul of the great monumental buildings of Sullivan, Mies, Burnham and Root and many others. Her post-lunch hour tour gives you a quick and easy introduction to some of the great public art and landmark buildings (including The Rookery!) that everyone should see when they’re in this great city. The meet up with Wendy on Wednesday, Thursday or Friday evening for a ‘Midcentury Nightlife on the Loop Tour’ that takes your group on an architecture walk that starts in the theater district and includes stop-offs for delicious apps at the legendary Berghoff and finishing up later with even more yummy food in the swanky lobby of the Palmer House Hotel. When we return, we’re definitely going to pick up where we left off with Wendy to find out more about this delightful city. A definite must-do! (Note: I’m talking about a couple of tours here, so the noon hour tour takes around an hour, allow a few hours for the evening tour.)  ~John P, Private Loop tour, 1950s Nightlife in the Loop

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