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Chicago might not be the most welcoming winter destination (freezing temperatures, harsh winds, damp air that chills to the bone), but looking forward to the warmer months in North America Chicago is one of the greatest cities to visit by car rental in the Midwest
Chicago is a fun-filled city, famous for it's blues, jazz, comedy, airplanes, shopping, and more. You could call it the cradle of the skyscraper, and Chicago features one of the most lovely skylines of any United States City. Shopping and dining abounds here. If it's fine dining you're looking for the Loop and downtown Chicago have you covered; if world flavors are your thing you can practically taste your way across the globe without ever leaving Chicago. Find out more about great restaurants in Chicago at Metromix. Reserve a cheap car rental for your spring or summer holiday in Chicago.
I drove to Chicago once from Louisville, Kentucky by car rental, and let me tell you, you don't want to get lost in Illinois! This was long before the 3g network and iPhones, if GPS was around it was still a government secret 'cause there sure were no car rentals with GPS; this was possibly even before Google Maps. I got impressively lost, at night, in nowheresville Illinois and had to stop and ask for directions to Chicago. I imagine that would be virtually impossible today.
My experience aside, Chicago is relatively easy to reach by car rental in the Midwestern United States, or you can fly into one of it's two primary airports, Chicago O'Hare and Chicago Midway. Reserve a car rental at Chicago O'Hare Airport to await the arrival of your flight.