Best time to visit Chicago for good weather
When is the best weather in Chicago? Monthly breakdown of temperature, rainfall, and sunshine hours — ranked by what actually matters for your trip.
Best month
September
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
↑Hotel rates dropping back to spring levels by mid-month
All months ranked — Good weather
Best match
The best Chicago month — 24°C lake breeze, jazz festival, Bears season opens at Soldier Field.
#1 for good weather
Best match
Chicago Marathon weekend (second Sun in Oct) — 50,000 runners through every neighbourhood.
#2 for good weather
Best match
Festival summer begins — Blues Fest (Jun), Pride Parade, beach culture at Oak Street and North Avenue.
#3 for good weather
Strong option
Patio culture explodes — 20°C lakefront, Riverwalk wine bars reopen, Memorial Day starts summer.
#4 for good weather
Strong option
Air & Water Show fills the lakefront sky — Blue Angels rip past Navy Pier at 500mph.
#5 for good weather
Strong option
Cubs season opens at Wrigley — first rooftop game and 14°C lakefront jogs.
#6 for good weather
Strong option
Lollapalooza, Taste of Chicago, 4 July fireworks at Navy Pier — the city at maximum volume.
#7 for good weather
Strong option
Magnificent Mile Lights Festival (Sat before Thanksgiving) — Mickey Mouse pushes the button, holidays begin.
#8 for good weather
Strong option
St Patrick's Day weekend — Chicago River dyed green, every Irish bar in Bridgeport packed.
#9 for good weather
Worth considering
Christkindlmarket fills Daley Plaza, Macy's windows on State Street, ice rink at Maggie Daley Park.
#10 for good weather
Avoid
The Hawk arrives — lake-effect wind chill hits -25°C, but Restaurant Week and museums are at their cheapest.
#11 for good weather
Avoid
Coldest month statistically — Chicago River dyed green begins planning, museum culture peaks.
#12 for good weather