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1. • Windy City Sailing

     Boat Rental & Charter, Boat Tours · 278.07mi

     Closed · 60 on TripAdvisor

     400 W Belmont Harbor Drive, G Dock · (773) 868-0096
     
   • Chicago Sailboat Charters

     Boat Rental & Charter, Boat Tours · 278.21mi

     Closed · 16 on TripAdvisor

     400 W Belmint Harbor Drive · (773) 236-7245
     
   • Chicago Private Yacht Rentals

     Boat Rental & Charter, Boat Tours · 274.56mi

     Closed · 1 on Yelp

     1559 S Lake Shore Dr · (224) 601-0220
     
   • 3rd Coast Charters

     Boat Rental & Charter, Boat Tours

     20 on TripAdvisor

     111 N Lake Shore Dr, Monroe Harbor · (844) 724-5987
     
   • Adventure Sea Tours

     Boat Rental & Charter, Tour Operator · 274.33mi

     Closed · 15 on Yelp

     Burnham Harbor · (773) 788-9494
     
   • SunSea Yacht Charters

     Boat Rental & Charter

     59 on Yelp

     1559 S Lake Shore Dr · (630) 323-5884
     
   • Charter Boat Chicago

     Boat Rental & Charter

     1 on Yelp

     111 E Wacker Dr · (312) 213-2628
   • The Sophisticated Lady Yacht Charters

     Boat Rental & Charter · 274.3mi

     Closed · 12 on Yelp

     1559 S Lake Shore Dr · (312) 970-5727
     
   • Prestige Yacht Rentals

     Boat Rental & Charter, Boat Tours · 277.49mi

     Closed · 1 on TripAdvisor

     2601 N Cannon Drive, Diversey Harbor · (312) 775-2288
     
   • Free Spirit Yacht Cruises

     Boat Rental & Charter, Boat Tours · 274.33mi

     Closed

     567 East Waldron Drive · (708) 361-2220
     
   • Uber Yachts

     Boat Rental & Charter, Boat Tours · 277.91mi

     Closed

     3100 S Lake Shore Dr · (312) 725-6366
     
   • XIII Charters Yacht Rentals

     Boat Rental & Charter · 273.35mi

     Closed

     3155 S Lake Shore Dr · (855) 734-9900
     
   • Party on Boats

     Boat Rental & Charter, Boat Tours · 275.11mi

     Closed · 4 on Yelp

     400 E Monroe St · (708) 304-8585
     
   • North Shore Marine

     Boat Rental & Charter · 278.48mi

     Closed · 14 on Yelp

     1438 W Cortland St · (312) 618-3448
     
   • Chicago WaterCraft

     Boat Rental & Charter · 275.65mi

     Closed · 10 on Yelp

     800 S Wells St · (773) 791-7311