For overall comfort, the top months for Chicago are usually September, June, August. These rankings use WanderingWeather’s proprietary monthly scoring built from long-term climate normals, so the score reflects how each month typically feels for travel.

Comfort is a relative score from 0–100 within Chicago. A month near 100 is one of the best weather months of the year for this destination; lower scores indicate more trade-offs such as higher rain disruption risk, more extreme heat or cold, or less predictable conditions.

Washout risk estimates how often a month tends to have weather that can disrupt outdoor plans (for example, heavier or prolonged rain days rather than brief showers). For example, washout risk can be around 4 days in September, versus about 7 days in April.

Volatility describes how changeable a month tends to be from day to day. Lower volatility generally means more predictable packing and planning; higher volatility means bigger swings in conditions, so layers and flexibility matter more.

Comfort favours broadly pleasant travel conditions, while Adventure leans more toward conditions that suit active outdoor plans. In Chicago, top Adventure months are often September, April, May, which can differ from comfort if the best hiking/outdoor conditions don’t perfectly match the most generally pleasant weather.

No. The rankings are weather-only. Peak tourist seasons and prices can be out of sync with the best weather months, so it’s worth balancing the weather score with flight/hotel pricing and major local events.

Often yes! It just means you should plan around the main trade-off shown in the table (for example, higher washout risk, more heat-risk days, or colder mornings/evenings). Use the Good/Mixed/Avoid guidance and packing tips to choose activities and clothing that fit the conditions.