Hey Chicago!
If you’ve been following along on our weekly blog, you know we cover a lot of topics related to Chicago: the beaches, pickleball courts, Michelin restaurants, school districts, and the bungalow belt are just a few of the more recent ones.
We try to put out something useful or interesting every week, but there’s something going on over on our social channels that we’ve never written about here, and it’s probably the most fun thing we do.
If you’ve come across Ben’s Instagram, TikTok, or YouTube Shorts, you may have already seen it. If not, keep reading!
In case we haven’t met yet, we’re the Ben Lalez Team, an award-winning real estate team in Chicago, helping people buy and sell homes across the city for over a decade. We rank in the top 0.01% of Chicago teams, with over $850 million in career sales and $200 million closed in 2025 alone.
Although we’re known for our real estate expertise, we try to bring value to Chicago residents beyond just transactions. That’s why every week, we publish these articles about living here. Subscribe to our newsletter if you want to see more of them directly in your inbox.
Now, let’s get into it.
How It Started
Sometime around October 2025, Ben started walking up to strangers on Chicago streets with cash in his hand and a simple offer: tour a nearby listing, guess the price, and walk away with money.
What started as an experiment has become one of our most popular segments. New episodes go up regularly across Instagram, TikTok, and YouTube Shorts, with each one set in a different Chicago neighborhood. The series has covered Wicker Park, Logan Square, River North, the West Loop, Old Town, and others, and Ben’s got a lot more ground to cover.
What Is “Guess The Price” And How It Works
The concept is simple: Ben walks up to a complete stranger on the street, cash visible in hand, and offers them $100 to tour a Chicago listing and guess its sale price. The stranger has never seen the property. They get a full walkthrough, make their guess, and depending on how close they get, they can walk away with money.
It’s part listing showcase, part personality video, part live game show.
If a stranger agrees to the challenge, Ben gives the full tour. Past listings have been stunning penthouses, a converted butcher shop turned loft space, and even a 20,000 square foot church with the original stained glass still in place.
At the end of the tour, the player guesses the price.
Of course, we’re not expecting anyone to guess the listing price to the dollar, so Ben will usually offer a range of prizes based on how close their guess is, and we’ve definitely met some market-savvy strangers who have made incredibly accurate predictions.
Some Of The Most Memorable Episodes
The Loop hasn’t been kind to Ben. There was a day when Ben approached someone on the street and launched into his pitch. The person completely ignored him and kept walking. Ben followed for a few steps, committing to the bit, shouting higher and higher cash amounts, $100, $200, $500, all the way up to $1,000, and the person never once slowed down or looked back. We all had a good laugh over that one.
In another Loop encounter, Ben barely got through his opening line before the person waved him off. When Ben clarified that it was free money, no catch, no strings, just guess a price and win, the person considered this for a moment and asked Ben to simply hand over the money directly. Ben did, and the person pocketed it and kept walking!
Outside of the Loop though, Ben’s had a bit more success. In the Logan Square episode, a couple played together, got close enough to win, and their reaction to splitting a $100 bill, screaming, grabbing each other, completely losing it over fifty dollars each, became one of our most popular clips.
You Don’t Have To Find Ben To Play
By the way, you don’t have to be standing on the right sidewalk at the right moment to participate. In every episode, you can drop your guess in the comments.
We’re pretty proud of the feedback we’ve had on our Guess The Price Segment. It’s gotten popular enough that other real estate agents around the country have started putting out their own versions of it.
Where To Watch
The series is on Instagram, TikTok, and YouTube Shorts. A few episodes to start with:
For the rest of the episodes, including several that never made it to YouTube:
- Instagram: @thebenlalezteam
- TikTok: @realestatechicago
- YouTube Shorts: @benlalezrealestate
Is Ben Still Out There?
Yup! New episodes go up frequently, which means Ben is regularly out on Chicago streets flagging down strangers. If you see a guy standing outside a building with cash in his hand, that might be your shot at a few hundred dollars.
If your ‘stranger danger’ signal is going off, don’t worry. We promise you’ll be safe, and you might even walk away with a bit of extra cash.
And if you can’t make it out there in person, drop your guess in the comments on any episode.
Final Thoughts
If there are any properties you see on our social media that you want to check out in person, make sure to let us know. We have access to many more listings that may not appear on every online portal.
If you ever find yourself in a neighborhood after watching one of these episodes and start wondering what it’s like to live there, give us a shout. That part we’re always happy to talk through.
And if you happen to walk by someone who fits Ben’s profile and he’s offering you a chance to win $100, slow down and hear what he has to say!
Until next week, Chicago!
