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Luxury & Exotic Car Rentals In Chicago, IL

Chicago is known as the Second City, however when it comes to luxury, it’s First Class all the way. Whether your needs call for a Ranger Rover Supercharged, Porsche 911 Turbo or anything in between, Imagine Lifestyles can surpass all of your expectations. If you want to coast down Lake Shore Drive on a summer day to experience the beauty of our Lake Front, rent a Bentley Continental GTC Mulliner Edition, or one of our other exotic luxury convertible rental cars, and feel the wind in your hair. Or maybe a Lamborghini Gallardo luxury car rental is more your taste because you want to see and be seen on Rush Street. What ever your destination or event may be, Imagine Lifestyles Luxury Rentals will help you feel First Class in the City.

Daily, weekly and monthly rates offered. Chauffeur service available.

Click here for our Chicago exotic rental cars.

Click here for our Chicago luxury rental cars.


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1956 Porsche 550 Spyder Rental in Chicago








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1965 Shelby Cobra 427 Rental in Chicago








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Aston Martin Vanquish Chicago








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Aston Martin Vantage Convertible Chicago








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Audi R8 Convertible Chicago








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Audi R8 Coupe Chicago








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Bentley Flying Spur Chicago








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Bentley GTC Convertible Chicago








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BMW 650I Chicago








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BMW 750 Li Chicago








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BMW X5 M Chicago








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BMW X6 Chicago








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Cadillac Escalade Chicago








Cadillac Escalade ESV Rental in Chicago

Cadillac Escalade ESV Chicago








Ferrari 458 Italia Chicago Rental Car

Ferrari 458 Italia Chicago








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Ferrari California Chicago








Ferrari F430 Coupe Rental

Ferrari F430 Coupe Chicago








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Ferrari F430 Spider Chicago








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Lamborghini Gallardo LP-560 Coupe Chicago








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Lamborghini LP560 Spyder Convertible Chicago








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Lamborghini LP700-4 Aventador Coupe Chicago








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Lamborghini Murcielago LP640 Chicago








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Lamborghini Murcielago LP640 Roadster Chicago








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Maserati Granturismo Convertible Chicago








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Maserati Quattroporte Chicago








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Mercedes Benz G550 Chicago








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Mercedes ML550 Chicago








Mercedes-Benz E550 Convertible Rental in Chicago

Mercedes-Benz E550 Cabriolet Convertible Rental Chicago








Mercedes GL450 Rental in Chicago

Mercedes-Benz GL450 Chicago








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Mercedes-Benz S550 Chicago








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Mercedes-Benz SL55 AMG Roadster Chicago








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Mercedes-Benz SLS AMG Coupe Chicago








Porsche 911 S Convertible Rental in Chicago

Porsche 911 S Convertible Chicago








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Porsche Cayenne S Hyrbid Chicago








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Porsche Panamera 4 Rental Chicago








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Range Rover HSE Supercharged Chicago








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Range Rover Sport Chicago








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Rolls Royce “Drophead” Convertible Chicago








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Rolls Royce Ghost Chicago








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Rolls Royce Phantom Chicago