Afternoon is the best time of a day to visit downtown Chicago.
Louisville is probably known for its historic buildings, art galleries & museums, as well as its music and bar scene. Depending on what you intend to do in Louisville, the best time of the day to head downtown is probably in the afternoons stretching into the evenings. On Main stree in downtown Louisville, there are various museums such as the Slugger Museum, Science Centre and Historial Arms Museum which are open to visitors.
However, since they tend to close early (except the Science Centre which closes 9pm on weekends), you will want to get in early to allow yourself ample time to see all the exhibits. If you are looking to visit some of the nightlight and the microbreweries in Louisville, then you might also want to get in during Happy Hour which usually lasts until 7pm or so.
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