Late spring · Weather & things to do
Chicago in May
The year's rain peaks now, with about 4.6 in (117 mm) falling in Chicago, alongside highs near 59°F (15°C) and lows of 47°F (9°C).
It scores 71/100 for comfort, 6th of 12, which makes it a solid shoulder-season month.
- Avg high
- 59°F (15°C)
- Avg low
- 47°F (9°C)
- Rain
- 4.6 in (117 mm)
- Humidity
- 83%
- Cloud cover
- 64%
- Daylight
- ~14 h 22 min
- Comfort score
- 71/100 · Good
What May feels like
Days are mild at around 59°F (15°C): comfortable for walking all day, with a layer for the evening.
After dark, temperatures fall to about 47°F (9°C).
Showers are part of the month, adding up to about 4.6 in (117 mm).
Plan around May
May is shoulder season: good weather, a step below the best months (July – September).
- Inside the wettest three-month stretch, April – June.
- Comfort improves from 59/100 in April to 71/100.
- Our Chicago & Great Lakes route recommends Jun – Sep, so May falls outside its suggested window.
- Our Chicago & Milwaukee route is planned for Late Nov – Dec 24, a window set by the holiday season rather than the weather — May falls outside it.
What to pack for May
- A warm layer for eveningsnights drop to 47°F
- Packable rain jacket or umbrellaabout 4.6 in of rain
- Comfortable walking shoesmost places below are best reached on foot or with short walks
What to do in Chicago in May
With conditions on your side, the picks below favor time outside.
Chicago Architecture Center River Cruise
90-minute docent-led boat tour of the skyscrapers along the Chicago River.
Why now Our curated notes say it's best May–Oct.
Chicago Riverwalk
1.25-mile path along the river's main branch with wine bars, kayak rentals and bridge views.
Why now May scores 71/100 for comfort, good conditions for being outside.
Magnificent Mile
Michigan Avenue's shopping stretch north of the river, with about a million lights strung through its trees in winter.
Why now Highs near 59°F and 4.6 in of monthly rain make this an easy outdoor pick.
Millennium Park
Cloud Gate, Crown Fountain and free summer concerts at Pritzker Pavilion.
Why now One to do outside while the weather is on your side.
The Walnut Room at Macy's
Marshall Field's 1907 dining room on State Street, where a Great Tree rises through the room each Christmas.
Lincoln Park Zoo
Free zoo set in a lakefront park, with conservatory and nature boardwalk nearby.
Nearby in May
- Indiana Dunes in May~34 mi · highs 69°F, 4.4 in rain · 5°C (10°F) warmer by day, about as wet
- Milwaukee in May~81 mi · highs 66°F, 4.3 in rain · 4°C (7°F) warmer by day, about as wet
- Holland in May~100 mi · highs 58°F, 4.1 in rain · similar daytime temperatures, about as wet
- Broad Ripple in May~159 mi · highs 73°F, 4.7 in rain · 8°C (14°F) warmer by day, about as wet
These averages also cover Lincoln Park and The Loop & Chicago River.
NASA POWER 2001–2025 monthly averages on a ~50 km grid. Comfort scores weigh temperature, rain, humidity and cloud: see how we score each month. Check a forecast before you go.
Chicago in May: quick answers
Is May a good time to visit Chicago?
It's a good shoulder-season choice, scoring 71/100 against a best of 85 in July – September. Expect highs of 59°F (15°C) and 4.6 in (117 mm) of rain. Our Chicago & Great Lakes route recommends Jun – Sep, so May is outside its suggested window.
How cold is Chicago in May?
Average highs are 59°F (15°C) and average lows 47°F (9°C), making it the 6th-warmest month by daytime highs.
Does it rain a lot in Chicago in May?
Some: about 4.6 in (117 mm) of rain falls across May on average, the wettest month of the year. The annual total is about 38.7 in (982 mm).
What should I pack for Chicago in May?
Bring a warm layer for evenings (nights drop to 47°F), packable rain jacket or umbrella (about 4.6 in of rain) and comfortable walking shoes (most places below are best reached on foot or with short walks).
Planning Chicago in May?
Bring the crew into one shared trip: vote on dates, build the day-by-day plan, split costs and share one packing list.