Best Time to Visit Chicago for a City Trip | Weather by Month

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City Trips Potential

92/100

Excellent

Based on optimal climate

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Seasonality

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Best Time

September, May, June

Avoid

Avoid (Extreme Weather)

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Weather

-4°C – 23°C

Avg Temp Range

Precipitation

Generally dry

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Good For

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Planning a city trip to Chicago?

The best time to visit Chicago for a city trip is September, May, June, when you’ll get the best balance of weather, atmosphere, and activities. If you're planning your visit during this period, it’s worth exploring the best areas to stay and things to do in advance.

→ Explore the best places to stay in Chicago

→ Discover top things to do in Chicago

Climate Heatmap

See at a glance which months offer the best city trips conditions — based on temperature, rainfall and climate scores.

Planning your city trip? Finding a central area to stay is key to exploring Chicago.

→ See where to stay in Chicago

City Trips conditions breakdown

Monthly weather & climate data for Chicago

Month	Climate Score	Predictability	Avg Temp	Max Temp	Rain (mm)	Rain Days	Humidity	Season
January	39Poor Cool temperatures. Some rain conditions.	Predictability 85Weather conditions are fairly consistent throughout the year.	-4°	0°	53	12.3	79%	shoulder
February	41Poor Cool temperatures. Mostly dry conditions.	Predictability 100Weather conditions are fairly consistent throughout the year.	-2°	2°	44	9.5	75%	dry
March	38Poor Cool temperatures. Some rain conditions.	Predictability 100Weather conditions are fairly consistent throughout the year.	4°	8°	62	11.7	69%	shoulder
April	58Suboptimal Cool temperatures. High rain conditions.	Predictability 85Weather conditions are fairly consistent throughout the year.	10°	15°	104	13.3	64%	shoulder
May	89Excellent Mild temperatures. High rain conditions.	Predictability 85Weather conditions are fairly consistent throughout the year.	16°	22°	103	13.2	67%	shoulder
June	83Excellent Mild temperatures. High rain conditions.	Predictability 100Weather conditions are fairly consistent throughout the year.	21°	27°	115	10.3	67%	shoulder
July	70Good Warm temperatures. Some rain conditions.	Predictability 100Weather conditions are fairly consistent throughout the year.	23°	29°	95	9.4	70%	shoulder
August	73Good Warm temperatures. High rain conditions.	Predictability 60Weather conditions vary somewhat by season.	23°	28°	105	10.8	72%	shoulder
September	92Excellent Mild temperatures. Some rain conditions.	Predictability 60Weather conditions vary somewhat by season.	19°	25°	88	9.3	68%	shoulder
October	77Good Cool temperatures. Some rain conditions.	Predictability 60Weather conditions vary somewhat by season.	12°	18°	82	10.5	69%	shoulder
November	39Poor Cool temperatures. Some rain conditions.	Predictability 100Weather conditions are fairly consistent throughout the year.	5°	9°	69	10.7	72%	shoulder
December	39Poor Cool temperatures. Some rain conditions.	Predictability 100Weather conditions are fairly consistent throughout the year.	-1°	3°	58	11.4	78%	shoulder