New York City and Chicago are close in May. New York City averages 13–22°C with moderate crowds; Chicago 11–19°C with moderate crowds.
By Daan · Last reviewed October 2026
New York City and Chicago
The verdict for May
Best overall
+The strongest balance of pleasant weather, city atmosphere, manageable crowds and reasonable value.
–Not the cheapest month — winter still wins on price.
Our best overall pick for most travellers.
Chicago at its sweet spot
+Chicago’s best weather window — warm days, cool evenings, rooftops back in full swing.
–Rates and crowds start climbing fast as the season turns.
Chicago’s best weather window — warm days, cool evenings, rooftops back in full swing.
Scores and crowd levels are my own judgement; temperatures are monthly averages. Higher scores are better: quieter, cheaper and more pleasant.
Another month