New York City edges it in June. New York City averages 18–26°C with high crowds; Chicago 17–25°C with moderate-high crowds.
By Daan · Last reviewed October 2026
New York City and Chicago
The verdict for June
Warm, lively and increasingly busy
+Long days make June excellent for the city, rooftops, parks and outdoor activities.
–Higher demand and less favourable pricing than spring shoulder season.
Excellent if you want a lively summer NYC experience.
Summer arrives
+Long daylight, lakefront beaches open, Blues Fest energy.
–Peak-season pricing kicks in and hotels fill on festival weekends.
Long daylight, lakefront beaches open, Blues Fest energy.
Scores and crowd levels are my own judgement; temperatures are monthly averages. Higher scores are better: quieter, cheaper and more pleasant.
Another month