Elliot Small Group
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With 15+ years of experience, the Elliot Small Group of Compass is passionate about real estate!
09/18/2026
Fall is a pretty great time to eat your way through Chicago. 🍂
Here are 5 of my personal picks for a fall food bucket list, from Chicago classics to cozy neighborhood spots and a good coffee stop.
➖ Ada Street
➖ Longman & Eagle
➖ Mott Street
➖ Mirra
➖ Oiistar
Whether you’re looking for a casual dinner, a weekend breakfast, or somewhere to grab a coffee, these are all worth adding to the list.
Save this for your next Chicago fall food crawl!
Elliot Small Group │ Chicago Real Estate
📱 847-373-0990
📧 [email protected]
09/16/2026
Chicago Restaurant Spotlight: Beaumonts 🍽️
When I first graduated from college, Beaumonts was a late-night 4am bar.
In 2024, Beaumonts was acquired by Bull Moose Hospitality, and the building went through a complete gut renovation. It recently reopened in 2026, and it’s definitely come back all “grown up.”
Now it’s a high-end tavern-style American restaurant with great drinks, food, and ambiance. We loved every minute of it.
Definitely recommend checking it out if you’re looking for somewhere new to try in Chicago.
Elliot Small Group │ Chicago Real Estate
📱 847-373-0990
📧 [email protected]
09/10/2026
If I were buying an investment property in Chicago today, I wouldn’t start with the property itself.
I’d start with the bigger picture.
➖ Neighborhood: I’d look at rental demand, walkability, transit, new businesses, and what’s happening around the property.
➖ Building: The right building needs to make sense beyond the listing photos. Unit mix, operating costs, condition, and rental potential all matter.
➖ Future development: I’d want to know what’s coming next. New development and investment can have a meaningful impact on how a neighborhood evolves over time.
The best investment isn’t always the most obvious one. It’s the one where you understand the fundamentals and see the opportunity ahead.
Save this for your next Chicago investment search.
Elliot Small Group │ Chicago Real Estate
📱 847-373-0990
📧 [email protected]
09/08/2026
We had a great time at Jacob’s 2nd Cubs game with my dad! ⚾️
We had great seats and a perfect sunny day to watch the Cubs play the White Sox. We took the train downtown, which Jacob always loves, and he had his first Polish sausage, which was a huge hit. He also got a snow-cone and we got to see the 2016 World Series championship trophy.
Unfortunately, the Cubs lost, but we still had a great time!
If this is your vibe, then you’re in the right place. 🍴
If you know me, you know I’m always looking for a new restaurant to try, a new dish to order, or an excuse to go back to an old favorite.
Chicago and the North Shore have some of the best food around, and I’m always happy to share the spots that make it onto my list. And yes, I have an actual list. 😂
DM me and I’m happy to send it your way!
Follow along for more Chicago favorites, from restaurants and neighborhoods to everything else that makes this city such a great place to live.
Elliot Small Group | Chicago Real Estate
📱 847-373-0990
📧 [email protected]
08/31/2026
A little scouting trip for the next great Chicago investment 😂🔎🏡
There are always opportunities in the Chicago market, but knowing where to look makes all the difference.
Whether you’re looking for your first investment property or adding to your portfolio, I’m always happy to talk through what’s happening in the market and where I’m seeing potential.
Looking for your next Chicago investment? Let’s connect! ⤵️
Elliot Small Group | Chicago Real Estate
📱 847-373-0990
📧 [email protected]
08/28/2026
ASK AN AGENT: WHAT MAKES A HOME WORTH THE PRICE? 💻️
When you’re looking at a home, it’s easy to focus on the things you can see right away: the kitchen, the finishes, the square footage, or a view like this one. 🌆
But determining whether a home is actually a good value takes a little more digging.
For a Chicago condo, I’m looking at:
1️⃣ Location. What does this neighborhood offer, and how does the location compare to similar properties?
2️⃣ The building. Amenities, condition, maintenance, and the overall health of the building matter just as much as the unit itself.
3️⃣ The monthly costs. HOA assessments, property taxes, and other expenses can significantly impact the true cost of ownership.
4️⃣ Resale. Consider what features could narrow your buyer pool when it’s time to sell. Things like the view, amount of natural light, or proximity to a busy street can all impact resale.
5️⃣ Comparable sales. Ultimately, I want to know how this home compares to similar properties that have recently sold.
A beautiful home is great. But the right value is about understanding what you’re actually getting for the price.
SAVE this post for your next home search, and DM me with your real estate questions.
Elliot Small Group | Chicago Real Estate
📱 847-373-0990
📧 [email protected]
If you know me, you know I’m always down for a good pizza. 🍕
Chicago has no shortage of great options, but these are 3 of my favorites:
1️⃣ Pequod's Pizza in Lincoln Park. Known for that caramelized crust and deep dish that has become a Chicago staple.
2️⃣ Piece Chicago. A Chicago favorite known for its delicious New Haven-style pizza and laid-back atmosphere.
3️⃣ Burt’s Place in Morton Grove. If you’re looking for a deep dish with a crispy, caramelized edge, this one is worth the trip.
Three very different takes on Chicago pizza, and I’d happily order from any of them.
Now it’s your turn! What’s your favorite pizza spot in Chicago? I’m always looking for new favorites to try! 🍕
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1643 N Milwaukee Avenue
Chicago, IL
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