Take into account high traffic times, especially near more metropolitan areas. The drive to and from the airport should be about 1h 28min, depending on traffic. There are 29.5 mi between Chicago Midway and Hollywood Casino Joliet. How far is Hollywood Casino Joliet from Chicago Midway?.You can usually find a nightly rate of $80 when staying at Hollywood Casino Joliet. Hollywood Casino Joliet is $50 cheaper than the average 3 star hotel in Joliet. How does Hollywood Casino Joliet compare to other 3 star hotels in Joliet?.