Chicago: Characters and Cons Guided Kayak Tour

Imagine paddling through the heart of Chicago’s bustling river while uncovering tales of deception, murder, and ambition from nearly a century ago. For $63 per person, you’ll spend about two hours exploring Chicago’s iconic waterways with a guide who’s passionate about storytelling. Led by a knowledgeable guide (whose name might vary, but one reviewer named “Sarah” as particularly engaging), this tour offers a perspective on the city that few other experiences can match. It’s a lively mix of history, scenery, and a splash of adventure.

What makes this kayak trip special? First, we love how it combines the physical activity of paddling with the storytelling of Chicago’s darker characters—like Leo Koretz, the 1920s con artist who duped high society with a fake trust. It’s a rare chance to see the city’s skyline from a different angle while hearing about real figures who shaped Chicago’s reputation for both wealth and scandal. Second, the tour’s focus on Jazz Age Chicago makes it more than a simple water excursion; it’s a journey into a time when fortunes were made and lost, and crime often went hand-in-hand with glamour.

However, a potential consideration is that this experience might not suit everyone. You need to be comfortable around water and have basic swimming skills. Also, since transportation isn’t included, getting to the starting point requires some planning. Nonetheless, for those craving an authentic, story-rich adventure with a small group atmosphere—limited to just six participants—this tour offers real value and a memorable perspective on Chicago’s history.

Key Points

• Unique perspective: Paddling through Chicago’s downtown offers unbeatable views of the skyline and river architecture.
• Engaging storytelling: Guides share captivating stories about figures like Leo Koretz and the Leopold and Loeb case, bringing Chicago’s past to life.
• Small group vibe: With only six participants, the experience feels intimate and personalized.
• Active adventure: Kayaking combines fun and exercise, making for a lively, memorable outing.
• Historical depth: The tour offers insights into Chicago’s Jazz Age and its darker side, enriching your understanding of the city.
• Weather considerations: The tour operates in most weather conditions, but be prepared for the elements with comfortable clothes and sunscreen.

You can check availability for your dates here:

Starting Off: Safety, Instructions, and First Paddles

Your adventure begins with a safety briefing and instructions on how to operate your kayak. Expect a friendly welcome from your guide, who will ensure everyone feels comfortable before hitting the water. If you’ve never kayaked before, don’t worry—the guide will cover techniques to keep you afloat and confident throughout.

For many, this initial step helps set the tone: fun, safe, and engaging. The small group size means personalized attention, and the guide’s enthusiasm makes the learning process smooth. As one reviewer praised, “Sarah’s knowledge and humor made the safety talk the most entertaining part.” This emphasis on safety assures you that the focus is on a relaxed, trouble-free experience.

Gliding Through Chicago’s Heart: The Scenic Route

Once on the water, you’ll paddle along the downtown section of Chicago’s river. Here, the architecture alone is worth the trip—gleaming skyscrapers, historic bridges, and vibrant city life all reflected in the water. But what truly elevates this tour is the storytelling. As you coast beneath bridges and past buildings, your guide narrates tales of Chicago’s characters—particularly Leo Koretz, a charismatic & notorious con man.

Koretz’s story is fascinating: he convinced wealthy Chicagoans to invest in a phantom oil trust, reaping millions before being exposed. Listening to these stories while watching the skyline is a rare combo that makes history come alive. One participant remarked, “We loved the way the guide wove in the stories of greed and deception, which added a thrill to the scenery.”

Uncovering the Dark Side: The Leopold and Loeb Case

As you paddle, your guide also reveals details of the Leopold and Loeb murder case—a notorious 1924 crime involving two wealthy university students who kidnapped and murdered a young boy. Interestingly, Koretz’s story is connected to the case, adding layers to Chicago’s reputation for criminal intrigue. It’s a compelling narrative that highlights the city’s complex past beyond its famous architecture.

These stories aren’t just dry facts; they’re delivered with flair, making you feel like you’re part of a local’s secret history. This storytelling approach turns a simple boat ride into a lively, engaging history lesson you’ll remember long after you land.

The Scenic End: Central Location for Further Exploration

The tour concludes at a central Chicago spot, perfect for continuing your adventure on foot. Whether you want to explore more of downtown, grab a bite, or visit a museum, you’ll find yourself conveniently located after this water-based history lesson.

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Practicality and Value

At $63 for two hours, this kayak tour offers a good balance of affordability and unique access to Chicago’s waterways. Comparing it to architecture cruises or lake cruises—often costing more—this experience provides a more active and intimate perspective of the city. Plus, the small group size enhances the feeling of exclusivity and personalized attention, making it a great choice for those who prefer a more relaxed, less crowded outing.

What the Reviews Say

Many past participants appreciated the combination of activity and storytelling. One reviewer said, “The stories were so engaging I forgot I was paddling,” highlighting how the guide’s narrative skills turn physical activity into a captivating experience. Others mentioned that the safety briefing was thorough but relaxed—an important factor for those new to kayaking.

While the experience is weather-dependent, wateriders typically operate in most conditions, so check the forecast and dress appropriately. Bringing a hat, sunscreen, water, and a camera will ensure you’re comfortable and ready to capture the scenery and stories.

Who Would Enjoy This Tour?

This tour suits history buffs, adventure lovers, and anyone craving a different view of Chicago. If you’re comfortable around water and enjoy stories about real figures who shaped the city’s reputation—both glamorous and infamous—you’ll find it rewarding. It’s especially ideal for those traveling in small groups or couples who want an active, engaging way to spend part of their day.

The Chicago Characters and Cons Guided Kayak Tour offers a distinct way to experience the city’s history from the water. It fuses physical activity with storytelling, giving you a layered understanding of Chicago’s past. Whether you’re fascinated by the daring con artist Leo Koretz or intrigued by the notorious Leopold and Loeb case, this tour delivers stories along with scenic views of Chicago’s iconic skyline.

While it’s not for everyone—those uncomfortable around water or with mobility issues might find it challenging—the experience rewards adventurous spirits with a memorable mix of history, scenery, and small-group charm. The price point is reasonable for the level of engagement and intimacy, making it a smart choice for those looking to explore Chicago in a different, more active way.

If you enjoy learning about the city’s less-glamorous past and want an authentic, hands-on experience, this kayak tour is well worth considering. It’s perfect for curious travelers who appreciate storytelling, scenic waterscapes, and a touch of adventure with their history.

Is this tour suitable for beginners?
Yes, the guide provides a safety briefing and kayaking instructions, making it accessible even for those new to paddling.

How long is the tour?
It lasts approximately 2 hours, giving you plenty of time to enjoy the scenery and stories without feeling rushed.

What should I bring?
Bring a hat, sunscreen, water, camera, and wear comfortable clothes. These items will help you stay comfortable and capture memories.

Are there any age restrictions?
The tour isn’t suitable for people with mobility impairments or non-swimmers, and basic swimming skills are recommended.

Can I cancel?
Yes, you can cancel up to 24 hours in advance for a full refund.

Does transportation to the start matter?
Transportation isn’t included, so you’ll need to plan to get to the starting point on your own.

What weather conditions does it operate in?
The tour runs in most weather conditions, but check the forecast and dress appropriately.

How many people are in a group?
The tour is limited to 6 participants, ensuring a small, personalized experience.

Is the tour offered in other languages?
This particular tour is offered in English only.

You can check availability for your dates here: