Boater missing from Playpen • 2 dead in crash near Cook County Jail • Record-high temps possible in Chicago

MONDAY NEWS FLASH - Chicago will be hit by a heatwave this week.

Each day between now and Saturday will have highs in the 90s. Each day will have mostly to partly sunny skies. 

A thunderstorm could pop up almost any afternoon but it is far more likely that drought-like conditions develop over much of the Chicago area.

Today’s record high is 96 degrees. It will likely fall. Peak heat indexes will flirt with 100 degrees this week but at this time no heat advisory is in effect. 

Boater reported missing after falling into Chicago's 'Playpen'

A search has been launched for a boater who fell into Lake Michigan Saturday afternoon in an area known as Chicago's "Playpen."

The male, whose age is unknown, fell off a boat into the water around 4:20 p.m. in the 1000 block of North DuSable Lake Shore Drive, according to police.

2 killed, 2 seriously injured in crash near Cook County Jail

Two people were killed and two others were injured in a crash near the Cook County Jail on Chicago's West Side.

Chicago police said two vehicles collided in the 2600 block of South California Avenue around 5:08 a.m. 

Multiple injuries were reported. A passenger in one of the vehicles was taken to Mt. Sinai Hospital where they were pronounced dead. A second passenger was taken to Stroger Hospital where they were later pronounced dead. 

A Special Wish Foundation fulfills dream for Chicago teen at WWE SmackDown

You're probably familiar with the Make-A-Wish Foundation. There's another wish granting organization that doesn't get as much publicity but helps families across the Chicago area with older children that have life-threatening conditions.

Nicholas Reyes, 19, has wrestled with a life-threatening condition for most of his life, but that didn't stop him from heading to WWE SmackDown in Philadelphia this spring, courtesy of a little known Chicago foundation called A Special Wish.

Pair of Chicago mass shootings leave 11 wounded

Eleven people were wounded in two mass shootings that took place roughly an hour apart Monday morning in Chicago's Humboldt Park and West Englewood neighborhoods.

The first mass shooting happened around 12:45 a.m. in the 900 block of North Pulaski Road. Police said a suspect shot into a crowd of people and fled the scene on foot. 

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If you owe the IRS estimated taxes, Monday is the deadline

The IRS is reminding taxpayers whose income is not subject to withholding that an estimated tax payment deadline is fast approaching.

Monday, June 17 is the payment deadline for second quarter estimated taxes. 

Here’s what Americans should know in order to avoid potential penalties in April 2025.