New York City edges it in December. New York City averages 1–7°C with very high crowds; Chicago -4–2°C with moderate crowds.
By Daan · Last reviewed October 2026
New York City and Chicago
The verdict for December
Cold, crowded and expensive — but magical
+Christmas lights, decorated streets, Rockefeller Center, holiday markets and department-store windows make this the most atmospheric month of the year.
–December is cold, and a high-demand, higher-price period — especially around Christmas and New Year's Eve.
Best overall isn't the same as most magical — New York at Christmas is one of the great travel experiences.
Chicago goes festive
+Christkindlmarket and Mag Mile lights make the city genuinely festive.
–Cold, and the week around Christmas/New Year’s pushes rates back up.
Christkindlmarket and Mag Mile lights make the city genuinely festive.
Scores and crowd levels are my own judgement; temperatures are monthly averages. Higher scores are better: quieter, cheaper and more pleasant.
Another month