Perched 1,353 feet above the glittering streets of downtown Chicago, a red and white checkered table awaits just steps away from the glass enclosed ledges that jut four feet out from the Willis Tower. It’s so quiet in the normally bustling office building that you can hear a pin drop. It’s after hours when the approximately 25,000 daily visitors to the Willis Tower have left. Our VIP Pie in the Sky dinner at Skydeck Chicago was definitely in our top 5 of the most unique places we’ve ever had a date night.ĭeep dish Chicago-style pizza and the ultimate view of Chicago Pie in the Sky VIP Dinner on the 103rd Floor Back up on the 103rd floor of the Willis Tower Skydeck, we enjoyed a deep dish pizza after hours at a table steps away from the glass-floored ledges that jut out of the Willis Tower. And we’re not debating which Chicago pizza joint has the best deep dish that’s a futile argument. This time, though, we couldn’t resist a Chicago deep dish pizza at one of the best seats in town.

We’ve been back to Chicago together a few times since, but we mainly skipped being tourists in his hometown. Aside from family time, we did all the touristy things one does in the Windy City: we ate all the things at Taste of Chicago, we met Sue at the Field Museum, we got splashed by the marine mammals at Shedd Aquarium and we took the elevator up to the 103rd floor of the (then Sears Tower) Willis Tower. Home just happened to be Chicago, and I’d never been there before. It was pretty much immediately love and a month or so later, he brought me home to meet the family. Tim and I met 17 years ago while we were both living in Las Vegas.

Book pie in the sky