Chicago: Sunset Kayak Tour on the Chicago River

If you’re pondering a unique way to see Chicago’s iconic skyline, this Sunset Kayak Tour might just be what you’re looking for. Offered by Wateriders Kayak Tours & Rentals, it promises to float you past some of the city’s most famous landmarks during that magic hour when the sun dips low and the glassy skyscrapers reflect a fiery sky. While I haven’t personally paddled through this tour, the carefully curated experience and glowing reviews suggest it’s a memorable blend of scenic beauty and laid-back adventure.

What makes this tour appealing? First, the setting during golden hour offers a view that’s hard to match from the ground — the sky changing colors, the city lights beginning to twinkle, and the calm water providing a perfect mirror. Second, the knowledgeable guides help ensure both safety and a richer understanding of Chicago’s architecture and history.

One consideration is that the group size can sometimes be large, which might lead to a slightly crowded experience—an important factor if you prefer more space or a quieter tour. This activity is best suited for travelers who enjoy outdoor activities, don’t mind getting wet, and are comfortable with basic swimming skills. It’s a fantastic choice for those wanting a different perspective of Chicago’s interior skyline, especially as the city lights start to glow.

Key Points

• Breathtaking Views: See Chicago’s skyline, including the Willis Tower and Civic Opera Building, from a unique angle during sunset.
• Leisurely Pace: Perfectly suited for all skill levels, with a relaxed schedule ensuring you enjoy rather than rush.
• Expert Guides: Guides are praised for their knowledge and patience, making the experience both fun and informative.
• Short Duration: At 1.5 hours, it’s an ideal activity to fit into an evening without taking up your whole night.
• All-Inclusive: Kayaks, safety briefing, and a guided experience come with the price, so no hidden costs.
• Limited Groups: Small groups (max 6) mean more personalized attention, though some reviews mention larger groups can get crowded.

You can check availability for your dates here:

A Detailed Look at the Tour

The Chicago Sunset Kayak Tour begins at a centrally located meeting point, making it easy to incorporate into an evening of exploring downtown Chicago. You’ll meet your guides, who provide a safety briefing and help you gear up for your paddle. The tour lasts about an hour and a half, during which you’ll glide along the Chicago River, taking in the city’s architectural marvels as the sun begins to set.

What makes this experience stand out? We loved the way the changing sky reflects off the glassy skyscrapers like the Willis Tower and the Civic Opera Building, creating a painterly scene. As you paddle, the reflection of the sunset on the river enhances the beauty of the cityscape, making for excellent photo opportunities.

Throughout the tour, you’ll pass notable landmarks such as the Merchandise Mart and other iconic Chicago structures. The guides take care to point out interesting details about these buildings, helping you appreciate the architecture beyond just the visual spectacle.

The leisurely pace means that even beginners or those with limited kayaking experience can enjoy this activity. There’s no rush, and guides are attentive to ensuring everyone feels comfortable, as one reviewer mentioned: “All of the guides are great and take their time to make sure you are comfortable before the fun starts.”

Expect to get a little wet—not necessarily soaked, but splashes are common on a river tour. A water-resistant camera or phone case is recommended to capture the moments without worry.

The tour concludes at a convenient central location, which facilitates easy access afterward for dinner or further exploration. It’s a good activity for an early evening, especially if you want to combine it with other city sights or just enjoy a peaceful paddle as dusk falls.

What’s Included and What You Should Know

The tour price of $58 per person covers kayak rental, a guided tour, and a safety briefing. No hidden fees here, and the tour operates in most weather conditions, making it a reliable choice. However, you’ll need to bring along your own camera, sunscreen, water, and comfortable clothes.

Participants should have basic swimming skills—think able to float or tread water—since safety is paramount. The activity isn’t suitable for those with mobility impairments or non-swimmers, but if you’re comfortable in the water, this tour is accessible and safe.

Transportation to the meeting point isn’t included, so plan accordingly—most travelers find it easiest to arrive by public transit or taxi.

The group size is limited to six participants, giving a more intimate experience, though some reviews suggest larger groups can sometimes feel crowded, especially with multiple kayaks on the water.

Cancellation policy: You can cancel up to 24 hours in advance for a full refund, providing some flexibility if your plans change.

Authentic Experiences and Honest Feedback

When looking at reviews, a common theme emerges: knowledgeable guides and stunning views are the highlights. Joel from the US gave a perfect summary: “This was a fun activity that puts you right in the middle of Chicago! All of the guides are great and take their time to make sure you are comfortable before the fun starts. Highly recommend!”

However, not all feedback was perfect. One traveler from Switzerland described a somewhat chaotic organization, mentioning that some canoes needed repairs and that guide explanations were limited. While this particular review was about canoeing, it hints at the importance of good management for a smooth experience.

Another reviewer noted that group size could be improved: “Ours was way too large and everyone kept running into one another.” While the small group limit is a plus, this suggests that if you’re sensitive to crowded conditions, it’s worth mentioning.

Who Should Consider This Tour?

This sunset kayaking adventure is ideal for outdoor enthusiasts, architecture lovers, and those wanting a relaxed, scenic experience of Chicago from the water. It’s perfect for couples, small groups of friends, or solo travelers eager for a different perspective on the city.

It’s also best suited for those comfortable with water activities and who can handle basic swimming skills. If you’re looking for a quick, memorable way to see the city in a peaceful setting, this tour hits the right note.

More Great Tours Nearby

Final Thoughts

The Chicago Sunset Kayak Tour offers a refreshing, scenic way to experience downtown Chicago’s famed skyline. For $58, you get a guided paddle past historic buildings, with the added bonus of witnessing a sunset over one of America’s most vibrant cities. The guides are well-regarded for their knowledge and patience, making this an accessible activity for most.

Though there are minor concerns about group size and organization, the overall experience appears to deliver on its promise of stunning views and a peaceful paddle. It’s especially suited for travelers who want to combine outdoor fun with a touch of culture and architecture, all during that magical golden hour.

If you’re seeking a memorable, low-key adventure that offers a fresh perspective of Chicago, this sunset kayak tour is worth considering. It’s a genuine way to enjoy the city’s beauty from a different vantage point — floating serenely along the river as the city’s lights flicker on and the sky paints itself in shades of orange, pink, and purple.

FAQ

Is the tour suitable for beginners?
Yes, the tour is designed to be leisurely-paced and suitable for all skill levels, including beginners. Guides focus on safety and comfort before heading out.

What should I bring?
Bring a camera, sunscreen, water, and comfortable clothes. A waterproof case for your phone or camera is recommended since you might get a little splashed.

How long is the tour?
The tour lasts approximately 1.5 hours, making it a convenient activity for an evening out.

Are food and drinks included?
No, food and drinks are not included in the tour fee. You’ll need to bring your own if you wish to snack or hydrate during the paddle.

What is the maximum group size?
The tour is limited to 6 participants for a more personalized experience, though some reviews note that larger groups can feel crowded.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, offering flexibility if needed.

Is transportation to the meeting point included?
No, transportation is not included. Plan to arrive by public transit, taxi, or personal vehicle.

Are there any restrictions on who can participate?
Participants should have basic swimming skills, and the activity isn’t suitable for those with mobility impairments or non-swimmers.

In summary, the Chicago Sunset Kayak Tour is a lovely way to see the city from a different perspective, especially during that brief window of sunset. It offers a good balance of scenic beauty, expert guiding, and relaxed paddling, making it a worthwhile addition to your Chicago itinerary—so long as you’re comfortable on the water and eager for a peaceful, beautiful adventure.

You can check availability for your dates here: