Here’s something incredible about Chicago.
My Friday venture takes me to the Sears Tower...
It's famously modeled after a pack of cigarettes. 🤯
What nobody told me before moving to Chicago.
- People say hi
- Weather is better
- Riverwalk is elite
- Architecture Tour
- Hot Dogs and Ketchup do not coexist
- There is a beach in the city
- Tavern Style > Deep Dish
- Highest ratio of best/most accessible restaurants in US
Discoveries that will make your next visit better. Ask me anything.
Brand new in Chicago.
Gibsons Tavern opens Nov 17th in Fulton Market as the prequel to Gibsons Steakhouse, set in 1918.
- Gibsons' Prime steaks and tableside Caesar
- Prohibition-inspired cocktails
- Cherries Jubilee flambéed at your table
Two rooms, two menus. Tavern Bar or Dining Room. Which is more of a vibe?
Opening a new spot in Chicago? DM me. I'll help make sure the city sees you.
More Chicago firsts weekly: investrly.substack.com
Six weeks ago we said "I do" here in Chicago.
The city has inspired us more than ever expected with so many top moments coming from your recommendations.
Chicagoans, what's the moment you knew this city was home?
Chicago restaurants are S-tier.
- La Scarola
- Gibson's Tavern
- Bavette's
- Gene & Georgetti
- Crying Tiger
- Spacca Napoli
- Girl & The Goat
My top 7 to still visit. Which one needs to be first?
How Chicago voted on 5 referendum questions:
84% Yes · Seek compensation for ICE operations
80% Yes · Millionaire tax to fund schools
74% Yes · Penalize vacant properties
72% Yes · Restart gunshot detection tech
67% Yes · Permanent festival and event space
All non-binding, but they could shape future legislation.
Which result surprised you most?
Nearly half a million of you read this. Chicago clearly wants the numbers behind the headlines.
I'm new to the city and have an open mind in sharing my exploration of it. Most importantly, I am focused on being a value add here to match the value you add to my journey.
If money, food, and investing early in the Chicago journey interests you, support Investrly. Let's work together to improve an all ready historic town.
Join free here 👇 DMs always open.
investrly.substack.com
I voted in Chicago for the first time today. It wasn't great.
- 1+ hour wait
- 8 machines, only 3 judges
- Zero updates while waiting
- Ballot scan at the end was great
Huge respect for the volunteers. But we should expect better. Here are three easy fixes:
- More judges. Open machines and a line that won't move is a staffing problem.
- Faster check-in. Scan the Voter ID instead of hand-filling a form.
- Real races. No one should run unopposed. Make every seat earn it.
Being new I'm paying attention to help fix it. What would you change?
You won’t believe this.
Another glorious fall day to enjoy the perfect 70º weather and incredible sights.
Chicago is an elite city.
Election Day in America.
My ballot had one issue on it: keeping the Bears in Chicago.
Sorry, Indiana. Not now, not ever. Who’s with me?
It's amazing being new to Chicago. Sharing my joys of exploring top experiences in this epic city just to see replies filled with nonsense, hate, and “wait for winter”.
Find a better reply. I’ve been through worse winters. Share a great rec and be happy for someone. GO BEARS.
I regret to inform you that once you've lived in Chicago, every other city's skyline looks like a rough draft.
The local Chicago coffee scene has been a great exploration for me. I’m still so new.
- Sawada
- Discourse
- Big Shoulders
- Metric
- Ipsento
- McDonalds
What am I missing and need to know?
My first October in Chicago is a wrap. Here are my highlights.
- Perfect Fall weather
- Epic Midwest foliage
- Lake Shore Path ride
- Green City Market
- Sears Tower lunch view
- Armitage Ale House Stick Date Cake
- Thin crust pizza: Pizz'amici and Zarella
- Italian sandwiches: JP Graziano, Nonna's, Tempesta Market
10/10 month. Where should I go first in November?
Here’s something incredible about Chicago.
The food is top tier offering every cuisine imaginable with new openings to old school classics.
The best restaurant I enjoyed this week was Armitage Alehouse.
Am I doing this right…
Perfect day to taste one of the best sandwich shops in Chicago.
Tempesta Market 🇮🇹
#13 The B. Franklin is a game-changer.







