Chicago 2024: Part One

We went on our first city vacation as a family this year, and we managed to get Connor sold on the idea of city vacations being a thing in the future.

For Connor’s first foray into the world of freeform roll-your-own city vacationing, we spent three nights in Chicago. Aaron and I hadn’t been to Chicago since our first visit some 14 years ago, and that was a couple years before Connor came on the scene. This time around, our only real agenda items were 1.) taking a hop-on, hop-off bus tour, 2.) eating at Ann Sather’s again, and 3.) trying Italian beef, all of which we successfully crossed off the list.

The gallery above features highlights from our arrival on Sunday, including deep dish Chicago pizza at Giordano’s; and our initial explorations on Monday, including our Big Bus Tour, a trip up the Willis (Sears) Tower, lunch at Luke’s Italian Beef, a brief (cold and windy) stop at Navy Pier, an afternoon shopping excursion, warming up inside the Apple Store, dinner at Shang Noodle, and dessert at Ghirardelli.

Footprints in the Snow

I had just flashed my usual I Love You 🤟🏻 to Connor as the school bus pulled away. When I turned to walk back up the driveway, our matching sets of footprints stood out to me in the morning snow. We wear the same size shoe now: his men’s size 8 tread-marks are on the left, and my women’s size 10 slide-prints are on the right.

This school year is the first that Connor has taken the bus in the mornings since Kindergarten, since the elementary bus pickup conflicted with my work schedule. During those elementary years, I drove him to school — either for Extended Time in the mornings before school, or directly to school on days when I worked from home. Those short drives to school were some of the best one-on-one times I’ve had with Connor, and I had mixed feelings about losing that time with him.

Luckily for me, he still likes having me wait with him for the bus — and not just because I have the iPhone app that shows where the bus is on her route.