Monday, April 13 | Millennium Park, Grant Park & the Gala
A perfect spring day along Michigan Avenue, and a glamorous evening to cap it all off.
With Alicia back in conference sessions, I headed out to spend the day exploring two of Chicago’s most iconic green spaces right along Michigan Avenue: Millennium Park and Grant Park. I couldn’t have asked for a better day for it — the spring weather was doing its thing, flowers were blooming, and the trees were just beginning to bud. Chicago in April can be unpredictable, but today it was showing off.
First stop, of course: Cloud Gate — the Bean. I know, I know — Alicia and I had already made the pilgrimage on Saturday morning. But honestly, it deserved a second visit. There’s something irresistible about that giant mirror-polished ellipse. I dare anyone to walk past it without stopping. The spring light hitting the skyline reflection was even more stunning than the first time.
From there I made my way over to Crown Fountain, one of those public art installations that’s hard to describe but impossible to ignore. Two 50-foot glass block towers flank a shallow reflecting pool, each displaying a rotating cast of Chicago residents’ faces. There’s something quietly captivating about watching the faces change — a reminder that this city is made of people, thousands of them, all with their own stories. I spent more time there than I expected.
The gardens throughout Millennium Park were absolutely beautiful — bursts of spring color everywhere, and the trees showing the first fresh green of the season. It’s the kind of scenery that makes you slow down and just take it in.
I then crossed over into Grant Park, which stretches right across Michigan Avenue from the Hilton Chicago — practically our front yard for the week. The flowers here were equally gorgeous. I wandered over to the John A. Logan Monument, a dramatic equestrian statue honoring the Union Civil War general and Illinois senator. It’s an impressive piece of sculpture, and it commands the park beautifully.
One of the unexpected highlights of the afternoon was simply paying attention to the architectural details of the park’s bridges. Chicago is famously a city of architecture, and even the park infrastructure reflects that — ornate stonework, decorative ironwork, and elegant design details that most people walk right past. I made a point not to.
And then — the evening. After a day on my feet, it was time to clean up and join Alicia for the Urgent Care Foundation Gala, held in the Hilton Chicago’s Grand Ballroom. I’ll be honest: I was not prepared for how spectacular that room is. Soaring ceilings, crystal chandeliers, ornate details at every turn — it’s the kind of ballroom that makes any event feel like a genuinely special occasion. The gala was a wonderful evening celebrating the work of the Urgent Care Foundation, and it was a perfect way to cap one of the best days of the trip.
Parks by day, Grand Ballroom by night. Not a bad Monday in Chicago. 🌷✨





Next up: Day 6 — More Chicago adventures ahead. Stay tuned!




