The highest-scoring months in Chicago are May, Jun, Aug and Sep.
Best months
May, Jun, Aug and Sep
Peak season
May, Jun, Jul, Aug and Sep
Off season
Jan, Mar and Dec
Temperature, rainfall and sunshine are measured. The visit score below is derived from those three (design spec §5.3)estimate.
Temp: -6.2°C – 0.1°C
Rain: 78mm
Sunshine: 4.9h/day
Visit score: 3.3/10
Temp: -4.1°C – 4.4°C
Rain: 44mm
Sunshine: 7.8h/day
Visit score: 4/10
Temp: 0.6°C – 9.1°C
Rain: 99mm
Sunshine: 8.2h/day
Visit score: 3.2/10
Temp: 5.3°C – 14.6°C
Rain: 82mm
Sunshine: 9h/day
Visit score: 4.7/10
Temp: 10.1°C – 19.2°C
Rain: 72mm
Sunshine: 10.9h/day
Visit score: 7.6/10
Temp: 16.9°C – 26.2°C
Rain: 86mm
Sunshine: 11.9h/day
Visit score: 8.2/10
Temp: 19.4°C – 27.3°C
Rain: 194mm
Sunshine: 11.6h/day
Visit score: 7.3/10
Temp: 18.8°C – 26.4°C
Rain: 75mm
Sunshine: 11.8h/day
Visit score: 9.1/10
Temp: 16.1°C – 23.9°C
Rain: 92mm
Sunshine: 9.9h/day
Visit score: 8.2/10
Temp: 10°C – 17.9°C
Rain: 79mm
Sunshine: 8.4h/day
Visit score: 5.6/10
Temp: 3.1°C – 9.8°C
Rain: 68mm
Sunshine: 6h/day
Visit score: 3.5/10
Temp: -3°C – 3.3°C
Rain: 68mm
Sunshine: 4.2h/day
Visit score: 3.1/10
The strongest months to visit are May, June, August, and September, when visit scores peak alongside warmer weather. June brings highs of 26.2C and nearly 12 hours of sunshine a day, while August offers highs of 26.4C with the highest visit score of the year at 9.1, supported by strong sunshine and moderate rainfall of 75mm.
The trade-off is that these strong months sit within the wider peak season of May through September, when the city is at its busiest. July stands out as the wettest month, with 194mm of rain despite still being part of the peak season, so travelers seeking sunshine without the heaviest rain may prefer June or August over July.
March – May
Mild temperatures and blooming gardens. A great time for sightseeing with fewer crowds than summer.
Packing tips
June – August
Warmest months with the longest days. Peak tourist season in most destinations.
Packing tips
September – November
Cooling temperatures and autumn foliage. Shoulder season with good deals on accommodations.
Packing tips
December – February
Coldest months with shorter days. Holiday markets and winter activities in many cities.
Packing tips
AI-written interpretation reviewed against the data above — claude-sonnet-5, generated September 21, 2026. Every number on this page comes from a dataset named here; the formulas are public.