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Chicago, IL Luxury Rental Cars

Chicago is known as the Second City because it has so much to offer, and a Chicago luxury rental car can get you everywhere. Imagine Lifestyles offer a versatile fleet of luxury car rentals to serve any purpose during your stay in Chicago.

Lake Michigan and the downtown skyline make the ideal backdrop and excuse to drop the top on a sports car rental like a BMW M6 Convertible, Aston Martin Vantage, or head-turning Mercedes S550 sedan! Get yours today and discover pure excitement!

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

Click here for our Chicago exotic rental cars.


Aston Martin Vanquish Chicago








Aston Martin Vantage Convertible Chicago








Bentley Flying Spur Chicago








BMW 650I Chicago








BMW 750 Li Chicago








BMW X5 M Chicago








BMW X6 Chicago








Cadillac Escalade Chicago








Cadillac Escalade ESV Rental Chicago








Maserati Granturismo Convertible Chicago








Maserati Quattroporte Chicago








Mercedes Benz G550 Chicago








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








Mercedes-Benz S550 Chicago








Mercedes-Benz SL55 AMG Roadster Chicago








Porsche 911 S Convertible Rental in Chicago

Porsche 911 S Convertible Chicago








Porsche Cayenne S Hybrid Chicago








Range Rover HSE Chicago








Range Rover Sport Chicago








Rolls Royce Ghost Chicago








Rolls Royce Phantom Chicago