Chicago 2024

I noticed we had a free stay at any Hilton property on our account. Benson loves trains so it seemed like the perfect time to ride the train to Chicago and stay in the Waldorf for a night!

Our train left early Monday morning at 6:35 am.

It was a pretty painless 5 hour ride to Chicago. We tried packing really light so everything would fit in our stroller. Once we got off the train we walked 20 minutes (1 mile) to Magnolia Bakery. YUM!

It was a little over a mile to our hotel, and we decided to just walk instead of getting an Uber. Ben fell right asleep.

We relaxed at the hotel, checked out the pool, played in the tub and got some food to snack on.

For dinner we walked down to Gordon Ramsay Burger. It was great and this strawberry milk shake was really good!

Benson didn’t get more than a 15 minute nap and so by 7pm we were all dead tired. We all fell asleep and were woken up by the turn down service. We originally were going to spend the day looking around Chicago, but the heat and exhaustion made us change our tickets to the 9:50 train. :) 5 1/2 hours later, we were back in St. Louis!