Tours & experiences · Chicago, Illinois
Chicago
Chicago in Chicago, Illinois. Food, bourbon, history, and local experiences from independent operators.
20 pontoons · 1 jet skis · 1 kayaks · 68 tours · 88 adventures
20 operators
Free Wellness Events
Hosted by Big Marsh Park · Chicago, Illinois
Adventure
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The Art of a City, Downtown Chicago Guided Walking Tour (Semi-Private)
Hosted by Babylon Tours Chicago · Chicago, Illinois
Tour
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Art Institute of Chicago Tour with Skip-the-Line Tickets (Semi Private)
Hosted by Chicago Museum Tours LLC · Chicago, Illinois
Tour
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Spray Paint 'n' Sip- Chicago
Hosted by Native 312 Events · Chicago, Illinois
Adventure
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Lincoln Park Zoo & Nature Museum Private Tour
Hosted by Chicago Museum Tours LLC · Chicago, Illinois
Tour
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Chicago: Downtown Tour
Hosted by Underground Donut Tour · Chicago, Illinois
Tour
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4 Hour Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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Full Day Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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One Day Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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Two Day Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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Three Day Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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1 Hour Kids Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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2 Hour Kids Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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4 Hour Kids Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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1 Hour Dirt Jumper Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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2 Hour Dirt Jumper Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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4 Hour Dirt Jumper Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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Full Day Dirt Jumper Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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1 Hour BMX Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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2 Hour BMX Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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4 Hour BMX Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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Full day BMX Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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Beverly Tour
Hosted by Brick of Chicago · Chicago, Illinois
Tour
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Free Bike Events
Hosted by Big Marsh Park · Chicago, Illinois
Tour
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Art Institute of Chicago Skip-the-Line Tour (Semi-Private)
Hosted by Babylon Tours Chicago · Chicago, Illinois
Tour
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57ft. Power Catamaran
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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72ft. Classic Chris Craft
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Chicago: Fulton Market Tour
Hosted by Underground Donut Tour · Chicago, Illinois
Tour
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37ft. Sea Ray Sundancer
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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46ft. Sea Ray Express
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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48ft. Sea Ray Flybridge
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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50ft. Sea Ray Sundancer
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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56ft. Sea Ray Sundancer
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Private Luxury Yacht Rental (12 Person Max)
Hosted by Chicago Boat Rentals · Chicago, Illinois
Adventure
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Chicago Skyline Sail
Hosted by Tall Ship Windy · Chicago, Illinois
Tour
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Captain Dave Krell
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop
Hosted by Inside Chicago Walking Tours · Chicago, Illinois
Tour
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Captain Justin Pasciak
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Hosted by Inside Chicago Walking Tours · Chicago, Illinois
Tour
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Captain Tony Cartagena
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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McLaren 720S
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Phantom
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Porsche 911 Turbo S
Hosted by DS Luxury · Chicago, Illinois
Adventure
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The World Within (Part One): Dazzling Interiors™ of the Loop
Hosted by Inside Chicago Walking Tours · Chicago, Illinois
Tour
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Art Institute of Chicago Tour by Art Historian with Skip-the-Line Tickets (Priva
Hosted by Chicago Museum Tours LLC · Chicago, Illinois
Tour
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Ferrari SF90 Stradale
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Aventador SVJ
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Ghost
Hosted by DS Luxury · Chicago, Illinois
Tour
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Acura NSX
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Huracán
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Aston Martin DBX 707
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Spectre
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Revuelto
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Phantom EWB
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Cullinan
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Chicago Loop Architecture Private Walking Tour
Hosted by Chicago Museum Tours LLC · Chicago, Illinois
Tour
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The Art of a City, Downtown Chicago Guided Walking Tour (Private)
Hosted by Babylon Tours Chicago · Chicago, Illinois
Tour
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Lamborghini Huracán
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Urus
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Porsche Taycan
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz AMG G63
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz Sprinter
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz S-Class
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Captain Doug Scroggins
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Glow- A Neon Street Art Workshop
Hosted by Native 312 Events · Chicago, Illinois
Adventure
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78ft. Power Catamaran
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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52ft. Sea Ray Sundancer
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Cadillac Escalade V
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Land Rover Range Rover
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Cullinan
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Aston Martin DBS
Hosted by DS Luxury · Chicago, Illinois
Adventure
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2026 Air & Water Show - Special Event!
Hosted by Tall Ship Windy · Chicago, Illinois
Tour
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Independence Day Weekend Kick Off Sail
Hosted by Tall Ship Windy · Chicago, Illinois
Tour
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Captain Adrian Tejeda
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Lamborghini Urus SE
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Meet Me in Chicago: Solos & Singles Adventure Club
Hosted by Bobby's Bike Hike · Chicago, Illinois
Kayak2
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McLaren Artura Spider
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Private Charter
Hosted by Angler Charters · Chicago, Illinois
Tour
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Rolls-Royce Spectre Primavera Edition
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Cullinan
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari Purosangue 1 of 25 WB
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari Portofino
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rancho El Grande Transfer
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Captain Ronnie Roberts
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain Russell Bergeron
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain Alex Castillo
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Chicago Lake Shore Cruise Tour
Hosted by DS Luxury · Chicago, Illinois
Tour
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Contemporary Chicago Blues ~LIVE~ with Michael Charles!!
Hosted by Tall Ship Windy · Chicago, Illinois
Tour
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Sea Ray 450 Believe Chicago
Hosted by Believe Chicago · Chicago, Illinois
Tour
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Chicago Vibes 440 Carver
Hosted by Believe Chicago · Chicago, Illinois
Tour
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The Christmas Tree Crawl: The Magic of Chicago at the Holidays
Hosted by Inside Chicago Walking Tours · Chicago, Illinois
Tour
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West Town Guided Instagram Street Art Tour
Hosted by Native 312 Events · Chicago, Illinois
Tour
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All That Glam: Chicago’s Art Deco Masterpieces
Hosted by Inside Chicago Walking Tours · Chicago, Illinois
Tour
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Mercedes-Benz G63 AMG
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Flying Spur
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Captain Marty McConville
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Global Street Foods of Uptown
Hosted by Chicago Foodways Tours · Chicago, Illinois
Tour
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Ferrari 812 GTS
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Aventador S
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Audi R8 Spyder
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Captain Rich Wallace
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Lamborghini Urus WB
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Ghost
Hosted by DS Luxury · Chicago, Illinois
Tour
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Rolls-Royce Cullinan Black Badge
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari F8 Spider
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Aston Martin DB12 Volante
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Continental GTC
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz Maybach EQS
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes Maybach GLS 600
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz GLC 63S AMG
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz G550
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Fireworks Cruise!
Hosted by Tall Ship Windy · Chicago, Illinois
Tour
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Beautiful Interiors and The Bean
Hosted by Chicago by Dave · Chicago, Illinois
Adventure
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Donut in the Sky
Hosted by Chicago by Dave · Chicago, Illinois
Adventure
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Private Boat Tour
Hosted by Chicago by Dave · Chicago, Illinois
Tour
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Original Chicago Pizza Tour
Hosted by Chicago Pizza Tours · Chicago, Illinois
Tour
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Ferrari F8 Spider
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Urus
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Phantom
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz Maybach GLS 600
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz Maybach GLS 600
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz G63 AMG Ed.1
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Cadillac Escalade
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Dawn
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari 812 Superfast
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari 488 Spider
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Urus WB
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Continental GTC
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Urus S
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Bentayga
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Huracán Evo
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari Roma
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Aston Martin DB 11
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari Portofino
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz AMG G63
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Flying Spur Mulliner
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Range Rover Sport SVR
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Jaguar F Type SVR
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Mercedes-Benz S580
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Tesla Cyber Truck
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Audi R8
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Audi RS Q8
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Dodge Charger SRT Hellcat
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari 488 GTB
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Lamborghini Huracán Evo Spyder
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Rolls-Royce Wraith
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Captain Jonathan Zietlow
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain Lisa Dixon
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Indoor Range
Hosted by Smokin Gun Worx · Chicago, Illinois
Adventure
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Aston Martin Vantage
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Jet Ski Rental
Hosted by Skyline Jetski Rentals · Chicago, Illinois
Jet ski2180 HP
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Captain Ian Barbosa
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Taylor Breutzmann
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Lamborghini Huracán Evo Spyder
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Ferrari Portofino
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Private Yacht Charter for Up to 25 Guests
Hosted by Angela's Charters · Chicago, Illinois
Tour
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Private Event Yacht Charter (26–49 Guests)
Hosted by Angela's Charters · Chicago, Illinois
Tour
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1 Hour Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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2 Hour Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
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Historical and Architectural Lake & River Tour
Hosted by Chicago Fireboat Tours · Chicago, Illinois
Tour
from $29 / trip
Hunk-O-Mania Male Revue Show - Chicago
Hosted by New Age Productions - HOM · Chicago, Illinois
Adventure
from $40 / trip
Diva Royale - Drag Queen Show Chicago
Hosted by Diva Royale Show · Chicago, Illinois
Adventure
from $40 / trip
Exotic Car Photo Session
Hosted by DS Luxury · Chicago, Illinois
Adventure
from $60 / trip
Lamborghini Chicago City Cruise Tour
Hosted by DS Luxury · Chicago, Illinois
Tour
from $75 / trip
Bikes, Bites & Views: Chicago's Signature Dishes Bike Tour - Adults (Ages 16+)
Hosted by Bobby's Bike Hike · Chicago, Illinois
Tour
from $79 / trip
Art Institute of Chicago Skip-the-Line Tour (Private)
Hosted by Babylon Tours Chicago · Chicago, Illinois
Tour
from $95 / trip
Captain Brian Haas
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain Chase Curtis
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain David Groover
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Capt Michael Gabiga
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain Dan Leslie
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain Michael Totten
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $125 / trip
18 FT Private Pontoon Cruise
Hosted by Chicago Boat Rentals · Chicago, Illinois
24 ft12
from $150 / day
Rolls-Royce Ride Tour
Hosted by DS Luxury · Chicago, Illinois
Tour
from $175 / trip
Captain Nick Bieker
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $300 / trip
22 FT Private Pontoon Cruise (Up to 10 People)
Hosted by Chicago Boat Rentals · Chicago, Illinois
24 ft12
from $350 / day
Car Display
Hosted by DS Luxury · Chicago, Illinois
Adventure
from $1,000 / trip
Private Events- Request Form
Hosted by Bettie's Chicago · Chicago, Illinois
Adventure
from $2,000 / trip