top of page

First Family Solo Trip - Chicago

We wanted to get out of town a few days before school started, so we booked a short weekend getaway to Chicago, IL.


We were full blown tourists - did all the things, walked all the places and had so much fun.


We spent Thursday night at our dear friends, Tracey and Tommy's. It was the first time our kids could play together and it was wonderful.

After getting checked into the hotel, we walked to the beach and Navy Pier. We soared to heights of nearly 200 feet on the Farris Wheel over Navy Pier, with incredible 360-degree views of Chicago and Lake Michigan. Theo got a piece of pizza the size of his head and the kids enjoyed the Carousel.

After Navy Pier, we rode a quad bike to the beach. The kids LOVED sticking their feet in the water.

We headed back to the hotel. Even though it was cold, we still braved the pool. Tim was the BEST and got in both days. (It was COLD!)

We had the BEST Italian Dinner of our lives, tucked away in a beautiful little neighborhood. Bongiorno's Cucina Italiana & Pizzeria. This is a family run restaurant and they pride themselves in providing the best homemade italian meal in the city. They are not wrong. Tim and I fell in love and will definitely be back!

M was at that hard age, where she wants to be a big girl and walk, but it still small enough where her little legs can get tired. We did a lot of carrying - including our walk home from dinner when she fell asleep in Tim's arms.

The next day, we started our morning on a family-friendly architectural boat tour. Short enough for the kids, but great historical information for the adults. Great views - a must do if you're traveling to Chicago.

After our boat cruise, we walked to Michigan Avenue and made our way to Millennium Park to see The Bean and outdoor art exhibits, Maggie Daley Park (perfect for kids) and Buckingham Fountain in Grant Park.

Madeleine LOVED this fun interactive, water art show. We weren't sure what it meant, but she loved dancing in it! Meanwhile, Theo loved climbing up, up and away.

After exploring the bean, we discovered the BEST hidden park, perfect for young kids. An outdoor adventure park - perfect for exploring and discovering new things.

We made our way to Grant Park where we took in all the beauty of Buckingham Fountain. The best part was when the win shifted and we had to RUN our way out of a water, rainfall.



We took a bike back to Navy Pier (close to our hotel).


We made our way back to the beach, with swim suits this time. A big highlight for Tim and I were sitting back and watching the kids play together on the beach for hours. They LOVED every minute.