If you’re considering a way to experience Chicago beyond its well-known deep-dish pizza and towering skyscrapers, the Chicago Architecture and True Crime History Tour offers a unique blend of visual splendor and shadowy stories. This tour, offered by Local Chicago Tours, promises roughly 1.5 hours of walking through some of the Windy City’s most iconic buildings and hidden crime stories, guided by passionate local experts. It’s a popular choice, with over 170 glowing reviews and a perfect 5-star rating, suggesting many travelers find it both entertaining and insightful.
What makes this experience particularly appealing? First, the expert guidance ensures you’ll get stories and details that go far beyond the usual sightseeing commentary. Second, the combination of architecture and true crime adds an unexpected edge, appealing to those who love layered histories and a bit of intrigue. However, a potential downside to keep in mind is that the tour is fast-paced, and some might find the walking distance stretches to around three miles. So, comfortable shoes are a must, and if you’re someone who prefers a more relaxed pace, this might feel a little brisk.
This tour seems best suited for those who want a deep dive into Chicago’s design and dark past without the hassle of long excursions or additional costs. Architecture enthusiasts, history lovers, and crime story aficionados will likely find it hits just the right notes.
Key Points

- Expert-guided storytelling brings Chicago’s architecture and crime tales vividly to life.
- The tour covers three major stops, each offering a unique glimpse into the city’s past.
- The value at $35 per person is justified by the engaging commentary and diverse highlights.
- Walking distance is approximately three miles, so comfortable shoes are essential.
- Tours are available most days, with flexible cancellation up to 24 hours ahead.
- The tour has received consistent praise for knowledgeable guides and engaging delivery.
The Chicago Architecture and True Crime History Tour strikes a fine balance between aesthetic appreciation and storytelling of the city’s darker side. This walking experience is carefully curated to show you some of the most beautiful buildings and hidden stories tucked away in downtown Chicago’s streets. Whether you’re a first-time visitor or a seasoned Chicagoan, this tour adds a fresh perspective that combines visual splendors with dark tales, making the city’s history come alive in a different way.
Starting Point and Logistics

The tour kicks off at 118 S Wabash Ave, a central spot easily accessible by public transport, which is a big plus for visitors relying on Chicago’s transit system. The meeting point is straightforward, and it’s only about a five-minute walk to the final stop at Chase Tower at 10 S Dearborn St. The tour lasts roughly 1 hour 30 minutes to nearly 2 hours, covering a walking distance of about three miles, so wear your most comfortable shoes—this is definitely a walking tour rather than a bus or trolley ride.
The mobile ticket system simplifies entry, and no additional admission costs are needed for the sites visited, making the overall experience quite affordable at $35 per person. Since gratuities are not included, tipping your guide is customary if you feel they’ve added value, which most reviews suggest is the case.
You can also read our reviews of more historical tours in Chicago
The Itinerary Breakdown
First Stop: Marshall Field and Company Building
The tour begins at the Marshall Field’s building, an iconic fixture on Chicago’s shopping landscape. Here, you’ll learn about not only the architecture but also the dark history of the Field family. The building is impressive with its historic façade, and as you stand there, your guide will share stories that bring the site’s past to vivid life. This stop only takes about 10 minutes, but it’s a great introductory point that sets the tone—showing how beauty and darkness often coexist in Chicago’s history.
One review notes, “Learnt fun (and some gruesome) facts behind buildings and old Chicago,” illustrating that the guide manages to blend fascinating facts with the city’s more sinister stories.
Second Stop: Downtown / The Loop
The core of the tour is a stroll through Chicago’s Loop, where you’ll see a variety of stunning architectural styles—from historic facades to modern skyscrapers. This part lasts over an hour and a tenth, during which your guide shares stories behind each structure, many of which hide darker histories. For example, some buildings have tales of crime, corruption, or scandal—stories that are often missed on typical sightseeing tours.
One reviewer highlights, “Very interesting and engaging! A nice mix of architecture and crime history,” confirming that this blend appeals to those wanting more than just pretty buildings.
Final Stop: Chase Tower
The tour concludes at Chase Tower, known for its fascinating illusion—a fitting end that ties into the theme of appearances versus reality. The stop is brief, about 10 minutes, but leaves you with a memorable visual experience.
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Guide Quality and Experience

The reviews consistently praise the guides, with many mentioning Joseph and Kris as particularly knowledgeable and engaging. Comments like “Joseph was super knowledgeable, quite entertaining and engaging,” and “Kris was very friendly, funny, and always ready to answer questions” indicate that guides are passionate about their material and skilled storytellers. Several reviewers also note that guides often tailor their commentary, making each experience feel personalized and fresh.
What Travelers Say
Many reviews mention how well the guides balance “interesting facts” with storytelling flair. One says, “He included interesting true crime stories that applied throughout the area,” emphasizing that the stories are contextually linked to the buildings and streets. Others appreciate the humor and enthusiasm guides bring, making what could be a dry history lesson into an engaging walk.
Considerations
While most find the pace suitable, some noted that it’s fast-paced, with a lot of ground covered. One reviewer mentions, “Very fast paced,” but also points out that it’s “an easy walk,” confirming that if you’re prepared for a brisk pace, you’ll do fine. Also, the group size, with a maximum of 999, is quite accommodating, ensuring you’re likely in a manageable group, making it easier for the guide to interact.
Value for Money

At $35, this tour is quite accessible, especially considering the depth of stories shared and the scenic sights. Since parking and admission are not extra, the price is mainly for the guide’s expertise and storytelling. Reviews consistently highlight the excellent value, with many stating they learned a lot, and some even discovering new facets of Chicago’s architecture and history after multiple visits to the city.
Authentic Local Flavor

What sets this tour apart is the local guide’s passion. Many reviews praise the guides for their knowledge, humor, and ability to connect history with the present-day cityscape. Learning about Chicago’s dark past—including crime stories and scandals—adds a compelling layer, making the experience both educational and slightly thrilling. This tour isn’t just about admiring buildings; it’s about understanding the stories behind them.
This experience is best suited for history enthusiasts, architecture lovers, and crime story fans who want a well-rounded, engaging walk through Chicago’s streets. It caters well to those who prefer a guided experience that’s informative and lively, rather than self-guided wandering. If you’re short on time but still want a rundown of Chicago’s highlights and hidden tales, this tour offers excellent value.
Because it involves a fair amount of walking, it’s ideal for those in good shoes and comfortable with a brisk pace. Families, couples, or solo travelers who enjoy stories as much as sights will find this blend appealing. And with the ability to cancel free of charge up to 24 hours in advance, it’s a flexible option that can adapt to your plans.
The Chicago Architecture and True Crime History Tour offers more than just a sightseeing stroll. It provides an immersive experience filled with stunning architecture, fascinating stories, and a glimpse into the darker aspects of Chicago’s past. The knowledgeable guides and engaging narration make this a memorable way to see the city, especially if you’re interested in understanding how history, design, and crime intertwine in Chicago’s story.
For travelers craving a short but meaningful exploration that combines visual beauty with storytelling depth, this tour hits the mark. It’s especially suited for those who value authentic local insights and don’t mind walking a bit to uncover hidden gems and secrets.
If you love stories of scandal, crime, and clever architecture, this tour will keep you entertained while providing a fresh perspective on the city’s iconic skyline.
Is this tour suitable for all ages?
Yes, most travelers can participate, but keep in mind the pace and walking distance. It’s best for those comfortable with a brisk walk and standing for periods.
How long does the tour last?
The tour lasts approximately 1 hour 30 minutes to 1 hour 45 minutes, depending on pace and group discussion.
What is the starting point?
It begins at 118 S Wabash Ave in downtown Chicago, a location accessible by public transportation.
Are there any additional costs?
No, there are no extra admission fees during the tour, but gratuities for guides are not included.
Can I cancel the tour?
Yes, cancellations are free if made at least 24 hours before the scheduled start. Refunds are not available for late cancellations.
What should I wear?
Comfortable walking shoes are a must, as the tour involves about three miles of walking.
Is there a limit on group size?
The maximum group size is 999, ensuring a manageable and engaging experience.
Can service animals join the tour?
Yes, service animals are allowed.
Will I receive a ticket or confirmation upon booking?
Yes, the ticket is mobile, and you’ll get confirmation immediately after booking.
Is there a guide available for questions during the tour?
Absolutely—guides are known for their friendliness and willingness to answer questions, making the experience interactive and informative.
This tour provides a well-rounded, lively way to experience Chicago’s architecture and its shadowy past, perfect for travelers seeking both beauty and stories, all at a reasonable price.
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