Paddle the Chicago River at twilight on a guided 90-minute kayak tour that highlights the city’s top landmarks in a peaceful setting with fewer crowds.
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Difficulty
easy
Duration
1.5 hours
Fitness Level
Suitable for all fitness levels; basic paddling ability recommended
Wildlife
History
The Chicago River’s course was dramatically altered in 1900 to reverse flow, a major feat in civil engineering.
Conservation
The tour provider supports river clean-up initiatives to maintain water quality and aquatic habitats.
Urban Kayaks
Paddle the Chicago River at twilight on a guided 90-minute kayak tour that highlights the city’s top landmarks in a peaceful setting with fewer crowds.
Urban Kayaks is a Chicago-based paddling company operating from Monroe Harbor that offers guided kayak tours, paddleboard classes, rentals, and instructor training. Specializing in urban waterways, the company runs a range of experiences on the Chicago River and Lake Michigan, including sunset and twilight paddles, fireworks tours from Navy Pier, and family-friendly rentals. Programs include beginner paddleboard lessons, youth kayak classes for ages 9–16, an after-school kayak class for ages 10–16, and a multi-day Level 2 kayak touring instructor certification workshop.
All activities are led by experienced instructors who prioritize safety, small group sizes, and hands-on learning. Equipment rentals include single and tandem kayaks and paddleboards suitable for beginners and confident paddlers. Seasonal lakefront rentals operate on weekends through mid‑September, while guided river and harbor tours run throughout the paddling season.
Urban Kayaks emphasizes education and progression with dedicated youth programs and formal instructor certification opportunities. The youth five-day kayak class and the five-day after-school format provide progressive skill development in a supervised environment. The Level 2 Essentials of Kayak Touring Instructor Certification is a four-day immersive workshop focused on teaching methods, group management, and risk management for aspiring instructors.
By combining guided exploration of Chicago’s architecture, waterfront history, and natural shoreline scenery with structured learning and equipment access, Urban Kayaks provides reliable, memorable paddling experiences for families, beginners, and prospective instructors. Booking is available online or in person at Monroe Harbor, with seasonal schedules and class details posted on the company's website. Safety briefings included before every activity.
Location
Chicago, IL
Paddles depart from Monroe Harbor
Age Range
Kids 9–16 • Adults 18+
Programs for youth and adults
Tours Offered
10 Experiences
From 1-hour rentals to 4-day courses
Instructor Training
Level 2 Course
4-day essentials of kayak touring
Reserve guided tours, youth classes, rentals, or Level 2 instructor training—check seasonal schedules and weekend rental availability through mid‑September.
Book Evening Slots Early
Sunset tours fill quickly due to limited availability and prime timing—reserve your spot ahead of time.
Wear Layers for Evening Chill
Temperatures can drop quickly on the river after sunset, so bring a light jacket or layers.
Secure Your Gear
Use waterproof dry bags or containers to protect phones and cameras from splashes.
Follow Guide Instructions
Stay close to the group and listen carefully to safety briefings for a relaxed, safe paddle.
Life Jacket
Safety first—your guide will provide a properly fitted PFD for the tour.
Waterproof Bag
Protect valuables and electronics from potential splashes on the river.
Warm Layers
Keep comfortable if temperatures drop during the evening paddle.
fall
Closed-Toe Water Shoes
Secure footing when entering and exiting the kayak along the riverbank.
summer