72 Hours in Chicago :: A Family-Friendly Adventure

72 Hours in Chicago :: A Family-Friendly Adventure

Recently, I had the opportunity to travel to a technology conference in Chicago and decided to let my almost 12-year-old son tag along, in hopes that he’d benefit from the chance to see the latest and greatest from the world of tech. He flies free with me on Southwest anyway, thanks to the companion pass, and I’ve always found Chicago to be such a fun place for big city adventure, with a little slower pace.

While I was quite busy with work during the day, the mild fall weather and endless list of activities gave us a chance to explore together each evening. We enjoyed a mixture of culture, history, and, of course, delicious food, and we managed to hit most of the must-visit spots.

Day 1: Sweets and Treats

The Museum of Ice Cream is a place that exists! And the ice cream tasting is unlimited! We started our adventure with this super sweet, delightful museum. It is a dreamland of colorful exhibits and interactive displays, like putt-putt and carnival games. Probably more appropriate for younger kids, but we still enjoyed exploring the rooms filled with giant gummy bears and a huge sprinkle pool. We also discovered that our ice cream limit is about two scoops.

At the Museum of Ice Cream, tasting is unlimited!

After satisfying our sweet tooth, we headed over to Lou Manali’s for our first taste of Chicago-style pizza. No trip to Chicago would be complete without trying this legendary food. The deep-dish pizza was delicious, and we debated whether it was better than New York. My son loved it, but I’m sorry to report that I still prefer that New York slice.

Chicago Deep Dish pizza
Chicago Deep Dish Pizza

Day 2: History, Landmarks, and Sports, Oh My!

After spending the bulk of my day walking the conference floor and catching up on work calls, we got to spend the afternoon exploring the wonders of the natural world at the Field Museum of Natural History. This museum is home to an incredible collection of fossils, artifacts, and interactive exhibits. He even took a picture with a dinosaur! 

The Field Museum of Natural History, picture with a dinosaur.

On our way back to the hotel, we were able walk-through Grant Park, where former President Obama gave his first acceptance speech, and where we found iconic landmarks like Buckingham Fountain and the famous “Bean” sculpture, officially known as Cloud Gate. The Bean was closed for maintenance, so we’ll have to get a picture the next time around. 

That night, the Saints were on Monday Night Football, so we had to find a place to post up to watch. What better location than the Harry Carey’s 7th Inning Stretch restaurant, adjacent to the Chicago Sports Museum. It’s a perfect stop where you can learn about Chicago’s sports history and even try your hand at some interactive exhibits. It was so fun to test our skills against famous athletes and I was horrified to discover that my son’s wingspan was longer than mine! (And approaching that of Scottie Pippen.) 

Fun at the Chicago Sports Museum
Fun at the Chicago Sports Museum

Day 3: Architectural Marvels 

The last day kept me out of the hotel for most of the day, which was fine, since he had some schoolwork to catch up on. So, we made plans for the evening Architectural Boat Tour. This iconic Chicago experience showcases the stunning skyline and discusses interesting aspects the city’s history and culture, including how city officials reversed the flow of the river. The most famous structure, Willis Tower (formerly Sears Tower), was once the tallest building in the world, but neither of us were brave enough to venture to its Skydeck, which includes a glass-floored observation room called “The Ledge.” No thank you!

We also saw the John Hancock Center, The Rookery Building, whose interior was redesigned by Frank Lloyd Wright, Aqua Tower, Chicago Water Tower, which survived the Great Chicago Fire of 1871, the Chicago Tribune Building and so many more iconic landmarks. It was a definite #momwin when my son announced that he was planning to build the Chicago skyline in Minecraft when we returned home. 

Our 72 hours in Chicago was filled with adventure, culture, history, and delicious food — and it’s only a two-hour flight from New Orleans. Even though he missed a couple of days of school, my son will cherish this experience, and all that he learned in the three days we had together. For me, I returned from the conference with not only some professional accomplishments, but also with a personal one: A treasure trove of family memories.

Stephanie Davi-McNeely
Stephanie Davi McNeely has been in and around the nonprofit fundraising space for nearly twenty years. She oversees development and strategic partnerships, for the ACE Mentor Program of America, a national nonprofit mentoring program based in Philadelphia. There she is responsible for corporate and individual fundraising initiatives, as well as the growth and development of national partnerships with design and construction firms. In her spare time, she plays mom’s league softball, watches her son play soccer, takes French class through the Alliance, and serves as the First Lady of the University of Holy Cross in Algiers. She resides in New Orleans, Louisiana with her husband and 11-year-old son.


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