Urban Kayak Tours: Chicago River & Lakefront Adventure

Explore Chicago like never before with Urban Kayaks as you paddle through iconic cityscapes and along the peaceful lakefront waters.

Last updated: Sep 2025

  • Historic & Sunset Tours: From $60 Twilight Paddle: From $50 Lakefront Rentals: From $25/hour

Description

Urban Kayaks offers a refreshing way to experience Chicago—from the water. Founded by two local brothers and their friend, the company invites guests to paddle through the heart of the Windy City, either on the Chicago River or along the Lake Michigan shoreline. With scenic views of Navy Pier, downtown skyscrapers, and Monroe Harbor, each route provides a unique perspective of the city.
At the Riverwalk location, guests can enjoy guided tours like the Historic Chicago Tour, Sunset Tour, and Twilight Paddle. All tours include training, life jackets, paddles, and knowledgeable guides who share stories about Chicago’s history and architecture. For those seeking more freedom, the Lakefront rental location at Monroe Harbor offers kayaks and paddleboards with hourly rentals for self-paced fun.

What's included

  • On-land training before kayaking
  • Use of kayak or paddleboard
  • Life jacket and paddle
  • Guided river tours with expert commentary (Riverwalk only)
  • Staff supervision during tours for safety
  • Access to Lakefront and Riverwalk locations
  • 10% discount at TacoRio Cantina for participants

Perfect for

For solo
For two
Outdoorsy

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Itinerary

  1. Arrive early to avoid traffic and locate the check-in point.
  2. Check-in and complete waiver (online or on-site).
  3. Receive training and safety instructions from staff.
  4. Gear up with life jacket and paddle.
  5. Begin tour or rental: Riverwalk: Join your guide and paddle past downtown landmarks. Lakefront: Launch solo from Monroe Harbor and explore the shoreline.
  6. Wrap up and return equipment.
  7. Optional: Head to TacoRio for food and drinks with a 10% discount.

Location

435 E, Chicago Riverwalk, Chicago, IL 60601

Show directions

Packing List

  • Comfortable water-friendly clothing
  • Quick-dry shoes or sandals
  • Sunscreen Sunglasses with a strap
  • Water bottle Waterproof phone pouch or dry bag
  • Change of clothes
  • Towel Light jacket (for evening tours)

FAQs

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