New York City edges it in November. New York City averages 6–12°C with moderate crowds; Chicago 2–8°C with low crowds.
By Daan · Last reviewed October 2026
New York City and Chicago
The verdict for November
Cooler, quieter and increasingly festive
+Autumn-to-holiday atmosphere with cooler, quieter streets.
–Thanksgiving and the start of the holiday season push demand up around specific dates.
Great for autumn-to-holiday atmosphere.
Quiet before winter
+Quiet and good value once Thanksgiving week passes — museums nearly empty.
–Cold sets in fast, and Thanksgiving week itself brings a short, sharp crowd spike.
Quiet and good value once Thanksgiving week passes — museums nearly empty.
Scores and crowd levels are my own judgement; temperatures are monthly averages. Higher scores are better: quieter, cheaper and more pleasant.
Another month