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1. • Chicago Sailboat Charters

     Boat Rental & Charter, Boat Tours · 278.21mi

     Open · 16 on TripAdvisor

     400 W Belmint Harbor Drive · (773) 236-7245
     
   • Captain Al's Charter Boat Fleet

     Boat Rental & Charter, Fishing · 275.24mi

     Open · 7 on Yelp

     400 E Randolph St, Ste 3110 · (312) 565-0104
   • Chicago Boat Rentals

     Boat Rental & Charter · 275.12mi

     Open · 1 on Yelp

     111 N Lake Shore Dr · (773) 236-7242
     
   • Adventure Sea Tours

     Boat Rental & Charter, Tour Operator · 274.33mi

     Open · 15 on Yelp

     Burnham Harbor · (773) 788-9494
     
   • Chicago Summer Breeze Boat Charters

     Boat Rental & Charter · 275.48mi

     Open · 1 on Yelp

      · (312) 617-2928
     
   • Free Spirit Yacht Cruises

     Boat Rental & Charter, Boat Tours · 274.33mi

     Open

     567 East Waldron Drive · (708) 361-2220
     
   • Chi-Town Boat Charters

     Boat Rental & Charter, Boat Tours · 273.35mi

     Open

     3155 S Lake Shore Dr · (708) 606-7440
     
   • XIII Charters Yacht Rentals

     Boat Rental & Charter · 273.35mi

     Open

     3155 S Lake Shore Dr · (855) 734-9900
     
   • No Rainy Days Boat Rentals

     Boat Rental & Charter · 276.03mi

     Open

     1 E Erie St · (630) 418-8366
     
   • Chicago Electric Boat Company

     Boat Rental & Charter, Boat Tours · 275.91mi

     Open · 57 on TripAdvisor

     300 N State St, Marina Level – Unit EE · (312) 644-6411
     
   • Knot My Boat Charters

     Boat Rental & Charter, Boat Tours · 277.57mi

     Open · 18 on TripAdvisor

     3155 S Lake Shore Drive, 31st Street Harbor, J Dock · (312) 971-0971
     
   • Denison Yacht Sales

     Boat Rental & Charter, Boat Sale & Service · 278.48mi

     Open

     3550 S Lake Shore Dr · (312) 971-9684
     
   • Big Boat

     Boat Rental & Charter · 275.07mi

     Open

     111 N Lake Shore Dr · (773) 236-7245
     
   • Chiami Boat and Jetski Rental

     Boat Rental & Charter · 270.55mi

     Open · 1 on Yelp

     6401 S Stony Island Ave · (773) 562-6431
     
   • Chicago WaterCraft

     Boat Rental & Charter · 275.65mi

     Open · 8 on Yelp

     800 S Wells St · (773) 791-7311