Tandem Kayak Rentals in Chicago

  • Duration:1-2 Hours
  • Level: Easy
  • Length: At your leisure
  • Schedule: 11am - 6pm

Kayak Chicago’s Historic Lakefront as a Couple

Enjoy a quiet and romantic paddle along Chicago’s iconic coastline and take in the views of our world world-class city! Lake Michigan is clean, fresh, and an open turquoise body of water for pure enjoyment.

This fun, unique adventure is the perfect way to spend an active afternoon or evening exploring Chicago! Our experienced and enthusiastic staff will help you get started, giving you the confidence to get you out on the water paddling and feel in charge as you navigate the calm Lake Michigan waters off of Ohio Street Beach.

Our tandem kayak rentals are perfect for couples looking for a romantic thing to do in Chicago. Whether it’s a date, anniversary celebration, or to just break off from the city and have some downtime on the lake, you’ll find a kayak rental is a great way to pass the time with your significant other. Single and tandem kayaks are available for rent.

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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