Because you asked, Chicago
Tonight is the 22nd Thursday night game the Bears have hosted. They have won 11 of them. Let's make it 12.
Go Chicago. Go Bears. 🐻
I got married last month. Here are 4 takeaways.
- She's usually right
- Happy house, happy spouse
- Midwestern girls are elite
- Chicago St. Regis is forever in my heart
Life is a journey. Make sure to enjoy the experience and make the most of everyday. Take nothing for granted.
I moved to Chicago eight weeks ago. Recent highlights.
- Coffee: Big Shoulders
- Lunch: JP Graziano
- Dinner: Adalina Prime
- Pizza: Pizz'amici
- Walking: 606
- Visiting: Wendella Architecture Tour
- Weather: Elite
- Steering clear: Calling it Willis
It remains 10/10 on relocation. Ask me anything.
I'm rebuilding my career and network in Chicago.
Writing all about all of it, from the spots to the moves, in my free newsletter relaunching this fall.
Join me and invest early.
investrly.substack.com
Everyone who keeps saying Chicago winters are the worst can take solace in knowing Chicago fall has been the absolute best.
The weather remains perfect and I'm enjoying every day.
Chicago restaurants are S tier.
- Monteverde
- Armitage Ale House
- Bavette's
- Tre Dita
- Smyth
My top 5 list to still explore and enjoy. Huge thank you for the recommendations to date. What am I missing.
Moving to Chicago has been the best move of my life.
- Got married
- Kind people
- Perfect weather
- Clean City
- Great food
The most underrated city in America. Incredible life upgrade.
Chicago is a top tier city.
I've lived in Los Angeles, New York, London, and South Florida. Yet I didn't know this till I moved here.
Why isn't this well known?
As a brand new Chicagoan…it’s time to reweigh in on one thing I’m extremely confident about.
The Bears staying in town. The Indiana talk is simply that. Just talk. It's not happening.
The city and franchise are one of the icons of the NFL. It’s in everyone’s best interest to keep the team in Illinois. And they will.
Don’t get me wrong.
Exploring and eating at new restaurants is great.
Cooking dinner with your family and spending time enjoying it is unmatched.
The Chicago coffee scene is HOT. My favorites to date.
- Big Shoulders Redeye
- Sawada Tokyo Style
- Discourse
- Metric
What am I missing and need to know.
Here’s something incredible about Chicago.
The food continues to be top tier and I’ve gotten reservations with little stress.
The best restaurant I enjoyed last week was Carmines.
A great discovery in Chicago…
The exclusive Sip & Guzzle pop up suite at the Four Seasons. Enjoyed the debut weekend concept bringing unique drinks from the #1 bar in North America to the city through March 2027.
Mile High Cocktail Club was memorable.
You won’t believe this.
It was another picturesque and glorious fall day in Chicago.
Fortunately it looks like the week ahead is more of the same. Elite city!
Spectacular Sunday for my first Open House Chicago. Here are my highlights.
- Chicago Architecture Center
- Chicago Loop Synagogue
- Columbia Yacht Club
- Federal Reserve Bank of Chicago / Money Museun
So far it’s a 10/10 schedule. Ask me anything.
What a feeling waking up early on a Fall Saturday morning to see an iconic skyline downtown.
Perfect weather. Beautiful buildings. Crisp air.
Chicago has elite vibes.
Chicago, what if I told you...
The happy wife happy life program has two exciting reservations this weekend.
- NY pop up arrives with a view
- Lebanese gastronomy
What if you told me what restaurants they are. Can you do it. 👀






