Sunset Kayak Rental on Lake Michigan

  • Duration:1-2 Hours
  • Level: Easy
  • Length: At your leisure
  • Schedule: 5.00pm

Kayak Chicago at Sunset on Lake Michigan

Paddle along Chicago’s iconic coastline at sunset and take in the electric views of our world-class city! Lake Michigan is clean, fresh, and an open turquoise body of water for our pure enjoyment.

This sunset kayak rental is the perfect way to spend a late afternoon exploring Chicago from the water! Our experienced and enthusiastic staff is ready and excited to get you on the water. A kayaking adventure is perfect for intermediate skill levels, couples looking for a romantic start to the evening, or anyone who wants to enjoy the calm of sunset on the lake.

The sunset kayak rental begins at Ohio Street Beach, a popular beach in the bustling downtown district of Streeterville. Here, you’ll get fitted with your life jacket, kayak and paddle. After an in-depth discussion of safety and lake etiquette, you will set sail!

Not far out from Ohio Street Beach, you’ll see unparalleled views of downtown Chicago that are sure to top your Instagram wall. You control the pace, whether to stay close to shore or paddle further out. The views continue to get better from different angles and as the sun gently slopes below the backs of the buildings, creating a gorgeous orange/yellowish glow behind the skyline.

Private booking opportunities also available for company team building and outings, youth groups, birthday parties, bachelor/bachelorette parties, or any large group looking to have a good time!

Rental Locations

Bobby’s Kayak Chicago World Headquarters
Ohio Street Beach, Downtown Chicago
600 North Lake Shore Drive, Chicago, Illinois 60611
Map to view our Meeting Location

Rentals Depart and Return to Ohio Street Beach in Downtown Chicago

Rental Details

  • Must be 18+ to rent kayaks and SUPs. Ages 13+ can paddle alone if adult (18+) guardian rents the equipment.
  • Tandem kayaks are suitable for Ages 4+ as long as with adult (18+) guardian.
  • Valid driver’s license or ID/Matching Credit Card required in order to rent.
  • Beginner kayakers are encouraged to paddle a tandem kayak with a more experienced partner.
  • Prior to departure, a safety talk and paddling tips will be provided.
  • Reservations online and advance payment required.
  • Rental hours may be interrupted due to inclement weather.
  • There is no guarantee we will be around after closing time. *Rentals must return by closing time or be issued a surcharge.
  • No reimbursements for under participation.

What’s Included

Price includes kayak/SUP and life jacket.

What To Bring

  • Dress for a variety of weather activities. Layers are always recommended because weather can shift quickly when on Lake Michigan. Wear clothing you don’t mind getting wet.
  • Bring a hat and sunscreen for sun protection.


  • Ohio Street Beach is a popular beach in Chicago’s downtown Streeterville neighborhood.
  • The Playboy Building is located on the lakefront in Streeterville,and has seen quite a show in its heyday.
  • Throughout WWI and WWII, Navy Pier was one of America’s largest pilot-training bases. Now a popular visitor destination, the pier is home to countless restaurants, boutiques, theaters, and amusement park rides.
  • Lake Michigan is part of the Great Lakes chain, which represents the largest surface of freshwater in the world, covering an area exceeding that of the United Kingdom.
  • The Wrigley Building is a skyscraper in downtown Chicago located on the Chicago River, modeled after a Spanish cathedral with French Renaissance details.
  • Lovingly nicknamed the “Corn Towers” for their distinct cob-like design, Marina City is a popular mixed-use parking and residential plaza located on the Chicago River.
  • The beautifully redesigned Chicago Lakefront trail is a stunning feat of recreational architecture, extending 20 miles with downtown Chicago as its central core.


Price: Daily
1 Hour Kayak Rental $35.99
2 Hour Kayak Rental $69.99



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