As we bid farewell to summer, our family embarked on a three-day journey to Chicago to celebrate my son's 8th birthday over the Labor Day weekend. Our itinerary was packed with exciting excursions, making memories that will last a lifetime. To streamline our adventures, I purchased a Chicago CityPASS®, which proved invaluable in organizing our activities.
Saturday, Sept. 2: Willis Tower, Navy Pier, and Harry Caray’s
Our adventure commenced with a swift flight from Nashville to O'Hare via Southwest Airlines. After a smooth journey, we hopped aboard the "L" Blue line. While the train ride was an enjoyable experience for our boys, managing two small children along with luggage proved to be a challenge. Despite this, we navigated our way to the Marriott Courtyard Chicago Downtown/River North, albeit with a bit more walking than anticipated, providing us with an impromptu city tour.
Eager to immerse ourselves in the city's allure, we wasted no time and headed straight to the iconic emblem of Chicago's skyline – the Willis Tower. Thanks to the CityPASS, scheduling our viewing time at the Skydeck was a breeze. Before ascending to the top, we indulged in a quick bite at the Shake Shack located at the tower’s base. Upon reaching the 103rd floor, over 1,300 feet above ground, the boys were captivated by the views of the city. Witnessing Chicago's vastness from such heights was a truly special experience for them.
Following our time at the Skydeck, we proceeded to Navy Pier for an architectural boat tour. Drifting down the Chicago River, we marveled at the architectural wonders that define the city's skyline. While I had enjoyed this tour over a decade ago, I was uncertain if it would capture the attention of my 5- and 8-year-old sons. However, to our delight, it became one of their favorite experiences of the trip. The leisurely pace of the tour provided us with a moment of respite after a day of travel, allowing us to soak in the sights.
After the tour, we explored Navy Pier, reveling in its vibrant atmosphere and iconic carnival rides. As evening descended, we indulged at Harry Caray’s for dinner, savoring classic American cuisine before concluding our day with a leisurely stroll back to our hotel. Now, if my kiddos would not have been completely gassed, we would have stayed for the fireworks, which I hear are incredible.
Sunday, Sept. 3: Adler Planetarium, Shedd Aquarium, Field Museum, and Giordano’s
Rising early on Sunday, we embarked on another day of adventure. We opted for an Uber to Millennium Park, unaware that the famous Bean sculpture was undergoing construction. Undeterred, we explored the park making our way to the Adler Planetarium. Unexpectedly, we encountered the annual Bike the Drive event, where cyclists of all ages bike Lake Shore Drive 30-mile loop. This encounter necessitated a detour to hail a separate Uber to reach the museum. Despite the delay, we embarked on an interactive journey through the cosmos at the Adler, igniting the curiosity of both my boys, who particularly enjoyed operating the rover robot.
After about 2 hours at Adler, we proceeded to the Shedd Aquarium, where we were entertained by a dolphin show and encountered a plethora of aquatic life, like sharks and belugas. Interactive exhibits allowed us to touch starfish, stingrays, and other marine creatures, making it a highlight for our boys.
After several hours at the aquarium, we ventured to the Field Museum, where we encountered the legendary Sue – the most complete Tyrannosaurus rex skeleton ever discovered. While I could have spent the entire day at the Field Museum with all the amazing exhibits, my boys' attention was fried after
exploring the dinosaur fossils and morning activities. Promising them a visit to the Lego store, we boarded a boat taxi to Navy Pier, enjoying the unique mode of transportation. After reaching the pier, we hailed an Uber to the Lego store, arriving just before closing time, allowing the boys to choose their sets.
After a day filled with exploration, hunger beckoned. Dropping off our Lego purchases at the hotel, we made our way to Giordano’s to indulge in deep-dish pizza, a quintessential Chicago experience. Each cheesy bite was savored as we recounted the day's highs and lows. Vaughan Reed's highlight was driving the rover at the planetarium, and Penn couldn’t decide between the dolphins and T-Rex Sue.
Monday, Sept. 4: Cubs Game and Farewell
On our final day in Chicago, we enjoyed a leisurely brunch at Crosby's Kitchen, walking distance to Wrigley Field, preparing for the day ahead. Armed with tickets, we made our way to the iconic home of the Chicago Cubs, Wrigley Field, for a memorable game. It was a bucket list experience for my husband to share this moment with our boys.
As the game concluded, we boarded the train back to the hotel to collect our luggage and bid farewell to the Windy City. Though our trip was packed with activity, the memories we created will be cherished forever. As we boarded our Southwest flight back to Nashville, my husband and I reflected on the magic of family travel and the joy of experiencing new adventures together, reaffirming the special place Chicago holds in our hearts.