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