Chicago, IL kicks off Thursday, May 21 with mostly sunny skies and a high near 57°F — but the Windy City is absolutely living up to its nickname today. Northeast winds of 15 to 20 mph, with gusts up to 30 mph, will cut right through any light jacket, so layer up before you head out to the Lakefront Trail or Lincoln Park.
Today’s Setup
The National Weather Service says high pressure parked over the northern Great Lakes is funneling in a cool, dry air mass off Lake Michigan, and temperatures will actually drift back toward 55°F by afternoon — that morning sunshine is a bit misleading. Rain chances sit at just 2%, so it’s a dry but blustery Thursday from Evanston down through the South Loop. A windproof beanie wool will go a long way on any exposed stretch near the water.
For allergy sufferers, the strong northeast lake breeze does help scrub airborne pollen — but if you’re sensitive, running a Levoit air purifier large room indoors tonight makes a real difference as tree season rolls on across the metro.
Rain and Wind Risk This Weekend
Friday, May 22 starts mostly cloudy and dry, but the National Weather Service forecasts showers possible after 1 PM CT, with a 30% precipitation chance during the afternoon. Friday night is the bigger concern: rain showers are likely, with a 70% chance, hitting hardest across the south and southeast portions of the metro through the Calumet corridor and into the south suburbs. Saturday brings some improvement with highs near 63°F, but spotty showers are possible through the holiday weekend — expect plenty of dry hours in between.
Cubs at Wrigley: Plan Your Gameday
The Chicago Cubs host the Houston Astros at Wrigley Field on Friday (May 22), Saturday (May 23), and Sunday (May 24). Friday’s afternoon game could catch light showers late, so tuck a waterproof phone pouch in your bag and sport a Chicago Cubs fitted cap that doubles as rain cover. A Chicago Cubs jersey is always the right call no matter what the sky does. Grab your seats via Get tickets on SeatGeek or Find tickets on StubHub.
Friday Night Events
Friday night has serious live music energy despite the rain. The SLIDE AWAY 2026 concert at Aragon Ballroom is indoors — no weather worries. But The KidLAROI at The Salt Shed Outdoors is open air, and with rain likely after dark, waterproof layers are essential. Also on the radar: the Sueños Festival at Grant Park on May 24 — the forecast looks mixed but not a washout, with many dry hours expected through the holiday weekend.
Dinner Tonight
A cool, gusty Thursday evening calls for something warming — a big pot of pasta or a quick stir-fry hits the spot perfectly. Need ingredients? You can order groceries on Amazon and have everything for tonight’s dinner delivered to your door.
Next Few Days
- Friday: High 58°F, mostly cloudy; showers possible after 1 PM CT, rain likely Friday night (70%)
- Saturday: High near 63°F; spotty shower chances, holiday weekend stays unsettled
- Next week: Somewhat above-average temperatures return across the metro; lakefront neighborhoods stay a few degrees cooler
