Chicago · Month comparison

September vs October

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

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
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
FactorSeptemberOctober
Weather score
10
9
Value score
6
7
Crowd score
6
7
Events score
8
9
Atmosphere
10
10
Avg high temp24°C17°C
Monthly rain85mm80mm
Daily sunshine9hrs7hrs

September trade-offs

  • ↓Labor Day weekend hotel and flight prices still peak
  • ↓School-year kids back — but adult travellers still common Tue-Thu

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 →September in detail →October in detail →
Scores compare months within Chicago. Climate data: Open Meteo ERA5 30-year normals (1991–2020). Methodology →