Chicago · Month comparison

October vs September

October ranks #1 overall vs September at #2. Chicago Marathon weekend (second Sun in Oct) — 50,000 runners through every neighbourhood.

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
September light on Chicago skyline from lakefront

September

#2 of 12 months

Best match

The best Chicago month — 24°C lake breeze, jazz festival, Bears season opens at Soldier Field.

  • ↑Chicago Jazz Festival (Labor Day weekend) — free, Millennium Park
  • ↑Bears NFL home opener — Soldier Field tailgate atmosphere
FactorOctoberSeptember
Weather score
9
10
Value score
7
6
Crowd score
7
6
Events score
9
8
Atmosphere
10
10
Avg high temp17°C24°C
Monthly rain80mm85mm
Daily sunshine7hrs9hrs

October trade-offs

  • ↓Marathon weekend hotel rates double; Loop streets closed
  • ↓First frost and possible early snow late month

September trade-offs

  • ↓Labor Day weekend hotel and flight prices still peak
  • ↓School-year kids back — but adult travellers still common Tue-Thu
See all 12 months for Chicago →October in detail →September in detail →
Scores compare months within Chicago. Climate data: Open Meteo ERA5 30-year normals (1991–2020). Methodology →