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Chesapeake can host a great trip at any time of the year, depending on what you are looking for. Chesapeake has a temperate climate, which it shares with the rest of the mid-Atlantic - meaning that the city enjoys four distinct seasons.
Summers are hot and humid, July and August being the warmest months, when the average high approaches 90 degrees and nighttime lows are typically above 70 degrees. The temperature has been known to break 100, so be prepared! Summer is the most popular time to visit Chesapeake, due to the city's proximity to the Virginia Beach Oceanfront, as well as the Outer Banks, Busch Gardens and Water Country USA.
Winters are cool, with average highs in the upper 40's to mid 50's, and lows in the mid 30's - though often the nights dip below freezing. Snowfall is only occasional but does happen once in a while. Spring and Fall are typically mild and pleasant, though Springtime pollen may cause some trouble for allergy sufferers. Still, Chesapeake's biggest festivals happen mostly in the Spring and Fall, drawing their fair share of visitors.
Rainfall is pretty consistent throughout the year; the difference between the monthly precipitation totals from the wettest month (July) to the driest (December or January) is only about 2 inches.