Lessons Learned: A Mommy-and-Me Trip to the City


I gifted my daughter a mommy-and-me trip to the American Girl store in Chicago for Christmas. She had been begging to go for years, and at the age of eight, I felt like she was finally old enough to remember and appreciate the experience. I spent weeks planning the trip, scheduling reservations for the doll salon and cafe, plotting out travel pit-stops and parking garages, and putting together a list of favorite Windy City attractions. American Girl was the main destination, but I wanted to add some extras to make it a full day of mother-daughter fun. 

The day’s events ended up being even more enjoyable than expected. American Girl brought all of the whimsy and sparked hours of entertainment for my daughter and her doll. (The store truly has the creative experience down to a science!) But it was our time outside of the mall that made the greatest impression. Here are five life lessons I learned from our trip to the city: 

Embrace Spontaneity

My daughter is quite the daredevil, so when it came time to plan out some additional activities, TILT at 360 Chicago was number one on my list. What could be more exciting than hanging over the top of the city at the John Hancock Center observation deck? Unfortunately, the weather put a dent in my plans. Thick cloud coverage is the ultimate enemy when it comes to spectacular skyscraper views. So I pivoted. We made the trek over to Navy Pier and jumped on the Centennial Wheel. Turns out, it was one of the best decisions of the day! My daughter couldn’t believe that I was letting her ride on a Ferris wheel in the middle of winter, and the strong winds + swinging gondolas still made for a thrilling experience.

Take Her Lead

I’m a sucker when it comes to urban planning and architecture. The Chicago drawbridges and Water Works buildings are some of my favorite landmarks in the Windy City, and I was excited to share them with my daughter. But, and this likely comes as no surprise, she wasn’t exactly keen about this plan. As we approached the Riverwalk, my eight-year-old looked me in the eyes and said, “Mom, I know this is what you want to do, but it’s not what I want to do.” She wasn’t rude or bossy. She was just honest. 

I had to stop myself for a minute and think about the purpose of this trip. It had been a gift for my daughter, and the excursions were meant to be child-centered. Expecting her to appreciate the historical significance of city landmarks wasn’t meant to be on this trip’s agenda, and she had used her voice to communicate her opinion respectfully. I took her lead, we turned around, and we made our way back up the Magnificent Mile. She found Michigan Avenue much more interesting! 

Welcome New Learning Opportunities

As a native suburbanite, my daughter has had very little experience navigating city streets. Chicago’s immense size made our girls’ trip the perfect opportunity to review street safety and awareness. In addition to some of these important tips, we also practiced using a map. My daughter thought it was hilarious that I kept having to check our location using the little blue dot on Google Maps. (I swear it feels different when you are walking instead of driving!) Needless to say, she stopped laughing when I handed her the phone, and she got to be the navigator. It certainly was a learning experience for both of us!

Talk About What You See

While exploring Chicago, my daughter was exposed to some of the harsher realities of city life. We came across several unsheltered neighbors on the streets, many asking for money or food. While a part of me wanted to shield my daughter from the hardships she was seeing, I could tell that she was curious. I used our walk as an opportunity for her to ask questions, creating space for important dialogue about homelessness. As future experiences arise, I hope that my words help my daughter avoid stereotypes and instead approach these situations with empathy and compassion.

You are Capable

Solo traveling is something I really enjoy. Traveling with a child, however, adds a whole new sense of responsibility. My excitement for this mommy-and-me trip was definitely coupled with anxiety. I wanted to make sure I did everything right to keep my baby safe and create a memorable experience. But, like any trip, there were times when things didn’t go according to plan. As much as I wanted to keep these struggles to myself, my little travel partner picked up on the irritation and watched me problem-solve. When we were exiting the parking garage at the end of the day, she lovingly exclaimed, “Mommy, you did it!” 

They say travel can boost your confidence, which proved true for me on this trip. I’m proud that my daughter got to witness my frustrations and successes. Hopefully, it will inspire her to do something just like it one day, to push out of her comfort zone and transform a simple girls’ trip into something truly special.