Welcome to the NFL, Caleb Williams—You’d Score Big With These Chicago Homes, Fit for a Top Draft Pick

The NFL is no stranger to sliding doors. If the Carolina Panthers hadn’t swung a draft-day deal to acquire the top pick in the 2023 NFL Draft, this year’s top pick would have been headed to Charlotte, NC, instead of Chicago.

But the Chicago Bears‘ savvy decision to swap with the Panthers last year means they’ll select this year’s top prospect. For all their trading acumen, the Bears come with their own baggage of what-ifs—namely the prior two quarterbacks that they’ve selected in the draft’s first round. Neither was the long-hoped-for franchise savior.

Justin Fields lasted three seasons with the Bears before the team traded him to the Pittsburgh Steelers in March. Mitchell Trubisky was selected second overall in 2017 and made it through four up-and-down seasons in Chicago, before being dumped in favor of Fields.

That means Caleb Williams shouldn’t think about putting down deep roots in Chicago. Perhaps he will become the next Tom Brady and stick around the Windy City for a couple of decades. But given the capricious career arcs of most NFL players, Williams should also consider the city’s high-end rental market.

Dollars and sense

We have some ideas for Williams as he begins to navigate his pro football career. Namely, he should consider the real estate market in and around Lake Forest, IL, home of the Bears headquarters. Yes, it’s about 35 miles north of downtown and Soldier Field, but being away from the bright lights of the big city can minimize those pesky distractions NFL types sometimes favor.

Thanks to the league’s salary cap, we already know how much Williams will make.

This year’s top pick is slated to sign a four-year deal worth $38.5 million, which means they’ll be quite comfortable for years to come. But the real money will flow if he makes it to a second contract, a seemingly reachable goal that’s remained elusive for a number of once-prized prospects. Just ask Zach Wilson or Trey Lance.

In love with Lake Forest?

So signed to a fat contract—but on a relatively short leash—Williams shouldn’t splurge on Lake Forest’s most expensive listing.

A $13 million mansion landed on the market just two weeks ago and offers an array of baller-worthy details, including a sport court; a synthetic, indoor ice rink; and a luxurious, wood-paneled office with views of Lake Michigan. It’s a statement home without a doubt, but a rookie probably should shy away from this caliber of home.

The current median list price in Lake Forest is a robust $1.5 million, which is in line with what we’ve seen past top picks spend on a first home.

So in that vein, we’d suggest a brand-new, four-bedroom residence priced right at $1,514,900. Players love a new place because it means much less upkeep and hassle (distractions!) off the field.

Offering 3,700 square feet and allowing the buyer to pick a few custom finishes, this two-story home with a first-floor primary bedroom means a weary body won’t have to trudge up the stairs for much-needed rest.

High-end rentals are enticing

The town also offers an array of luxury rentals, should Williams opt to set home ownership aside for a few seasons. There’s a five-bedroom home available for $9,500 a month, a six-bedroom home on the market for $9,750 a month, and a grand brick residence at the highest end of the market at $15,000 a month.

But we’d also applaud him if he decides to save a few dollars and rent a basic, two-bedroom apartment in town for only $2,100 a month.

Going farther afield in search of a home

Williams might also consider a suburban town like Highland Park.

After all, it was a nice enough place for basketball legend Michael Jordan, who built a 32,683-square-foot mansion there. (Which, by the way, is still available for $14,855,000 after over a decade on the market.)

But if Williams sets his sights on more affordable real estate, there’s a brand-new modern farmhouse on the market for $2.2 million. Featuring four levels and six bedrooms, this place surely has space to carve out a sweet media room with an enormous television.

As for the city of Chicago itself, there’s plenty of allure. With over 10,000 active listings, it also offers an array of options.

A brand-new home priced at $2,050,000 in the city’s West Lakeview neighborhood might be interesting for an NFL rookie. With over 4,200 square feet of living space and six bedrooms, Williams could even easily take on a roommate and begin bonding with his new team.

Or to really live life to the fullest in Chicago, a 24th-floor pad at The Residences at 900 might be just the ticket. The three-bedroom, $2,750,000 unit serves up gorgeous views of the lake and surrounding skyscrapers. Close to high-end shopping and dining, the building offers a 24-hour doorman and valet parking for residents. Would the perks be enough to outweigh the commute? Welcome to the working world, Caleb Williams!

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