New York City and Chicago are close in October. New York City averages 11–18°C with moderate crowds; Chicago 9–16°C with moderate crowds.
By Daan · Last reviewed October 2026
New York City and Chicago
The verdict for October
Excellent autumn city weather
+Comfortable temperatures make October ideal for walking Manhattan and exploring neighbourhoods.
–A popular month, so rates stay firm.
One of the strongest months for a classic NYC city trip.
Crisp fall city days
+Crisp, clear walking weather and Chicago’s architecture at its best with fall color.
–The Chicago Marathon weekend (Oct 11) fills hotels and closes major roads.
Crisp, clear walking weather and Chicago’s architecture at its best with fall color.
Scores and crowd levels are my own judgement; temperatures are monthly averages. Higher scores are better: quieter, cheaper and more pleasant.
Another month