Above all, the rule for Shanghai is to lay low during (or altogether avoid) the Chinese New Year; the city grinds to a halt and public transport is flooded. The rest of winter offers good hotel discounts and few tourists.
Summer is peak season and gets a bit muggy, while from September to November the temperate weather brings out several interesting arts festivals and fairs. These are probably the best months to visit, but trade fairs and conventions do little to bring the prices down from peak season.
Shanghai starts the year shivering in midwinter, when temperatures can drop below freezing and the vistas are grey and misty. Spring brings warmth; April to mid-May is probably one of the best times to visit weather-wise, along with autumn (late September to mid-November). In summer the hot and humid weather makes conditions outside uncomfortable, with temperatures sometimes as high as 40°C (104°F) in July and August. In short, you'll need silk long johns and down jackets for winter, an ice block for each armpit in summer and an umbrella wouldn't go astray in either of these seasons.
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