Chicago · Month comparison

May vs October

October ranks #1 overall vs May at #4. Chicago Marathon weekend (second Sun in Oct) — 50,000 runners through every neighbourhood.

Chicago Riverwalk patios in May

May

#4 of 12 months

Best match

Patio culture explodes — 20°C lakefront, Riverwalk wine bars reopen, Memorial Day starts summer.

  • ↑Chicago Architecture Foundation River Cruise at peak (best 90 min in the US)
  • ↑Patio season fully open — RPM, Bavette's, Avec all spilling outside
Chicago Marathon runners through downtown

October

#1 of 12 months

Best match

Chicago Marathon weekend (second Sun in Oct) — 50,000 runners through every neighbourhood.

  • ↑Chicago Marathon — World Marathon Majors event, the entire city stops to watch
  • ↑Lincoln Park and the lakefront in red-and-gold maple
FactorMayOctober
Weather score
8
9
Value score
6
7
Crowd score
6
7
Events score
8
9
Atmosphere
9
10
Avg high temp20°C17°C
Monthly rain100mm80mm
Daily sunshine9hrs7hrs

May trade-offs

  • ↓100mm rain in spring storms; tornado watches possible
  • ↓Memorial Day weekend hotel rates jump 40%+

October trade-offs

  • ↓Marathon weekend hotel rates double; Loop streets closed
  • ↓First frost and possible early snow late month
See all 12 months for Chicago →May in detail →October in detail →
Scores compare months within Chicago. Climate data: Open Meteo ERA5 30-year normals (1991–2020). Methodology →