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I have been to Vegas every month of the year. The best time for me (weatherwise) would be September/ late May-early June. The cheapest time- July, August, December between the ending of the rodeo and a few days before NYE. The most expensive time- no contest- NYE.
Labor Day in Vegas. Labor Day Weekend in Las Vegas is usually the last really big weekend of the summer and pool parties. The weather in Las Vegas is usually still warm enough to enjoy the pools through the end of September and sometimes even into the middle of October.