Chicago is home to the Bulls, Bears, Cubs, Sox and Hawks, legendary hot dogs, deep-dish pizza and Italian beef (the true local delicacy) plus an iconic skyline. If you’re looking for a great driving city, look no further than Lake Shore Drive, stretching between miles of Illinois’ Lake Michigan shoreline and hundreds of soaring high-rises. Head over to our Chicago Travel Guide to round out your adventure. Looking for a cool car to drive along the Mag Mile and State Street or a classic car to start a Route 66 road trip? Check out DriveShare’s most popular cars available for rent in Chicago, listed below.