Glide beneath Chicago’s shimmering skyline on Urban Kayaks’ Twilight Paddle, a serene one-hour night ride through the city’s illuminated waterways. Discover urban beauty and quiet river moments after dark.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
1 hour
Fitness Level
Participants should have a basic level of fitness and comfort paddling in calm water conditions at night.
Wildlife
History
The Chicago River was famously reversed in 1900 to protect Lake Michigan's water quality, a remarkable engineering feat still affecting the river today.
Conservation
Urban Kayaks emphasizes Leave No Trace principles and partners with local groups to keep the river clean and vibrant for recreational use.
Urban Kayaks
Glide beneath Chicago’s shimmering skyline on Urban Kayaks’ Twilight Paddle, a serene one-hour night ride through the city’s illuminated waterways. Discover urban beauty and quiet river moments after dark.
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.
Bring a waterproof flashlight
A small waterproof light helps you navigate and signal others safely during the night paddle.
Dress in layers
Even summer nights can be chilly on the water—wear moisture-wicking and insulating layers for comfort.
Secure loose items
Night paddling means extra care to keep phones and cameras safe and dry in waterproof containers.
Arrive early for safety briefing
Prompt arrival ensures you receive important guidelines to navigate the river confidently after dark.
Personal flotation device (PFD)
Required for safety during all kayaking excursions.
Waterproof flashlight/headlamp
Illuminates your path and signals others on the water after dark.
Layered clothing
spring
Waterproof dry bag
Protects personal belongings from water exposure.