See how we spent a holiday weekend in Chicago with our toddler 

We spent a weekend in Chicago with our toddler during the holidays, and let me tell you…sometimes a quick weekend trip with a three-year-old is the best and easiest kind!

Read on to hear about what we did, where we stayed, where we ate – and why Chicago is a great destination for traveling with little kids.

All aboard! Train ride = ultimate toddler adventure

Quite frankly, the main reason we decided to go on this trip was not to experience the magic of Christmas in Chicago with our toddler. Rather it was because he absolutely loves trains and we could take a short Amtrak ride into the city. Let me tell you, it did not disappoint, aside from the conductor not saying “all aboard!”, as my son was hoping. My toddler was mesmerized the entire ride, and we got to skip the worst part of the trip, gridlocked traffic into the city. So I’d say the train ride was a win-win for the whole family.

Where we stayed in Chicago: Why the Westin Chicago River North is great for families

If there’s one thing about me, it’s that I love everything about hotels. I love researching them, picking our room, exploring the property when we arrive, and I have pretty high standards. This was our first time staying at the Westin Chicago River North, and we loved it! 

I thought it was a very family-friendly and accommodating option for families traveling to Chicago with young kids. I emailed a day ahead of time to ask for a crib in our room. Our son still sleeps in one, and I’m knocking on wood as I type this, but he’s never tried to get out.

The hotel responded to my request quickly, AND said they’d do anything possible to get us an early check in since we were traveling with a small child. It’s that extra level of service that goes such a long way and I wish more hotels offered. 

We arrived at the hotel really early, so I definitely did not think there would be a room ready for us. But to my surprise, there was! We were able to check in, drop off our bags and relax for a few minutes before heading out to explore Chicago. As if this all wasn’t great enough, they gave us two bags of Garrett’s Popcorn as a welcome gift. As you can imagine, they were consumed almost immediately.

What we did in Chicago: The Field Museum is great for dinosaur-loving toddlers

Dinosaurs might just be the only thing that can compete with trains for our toddler’s interest. So, we were very excited to take him to the Field Museum. 

If you haven’t been, it’s a huge museum with three floors of natural history. We didn’t even make it halfway through (before someone needed a nap), so we’ll need to go back! 

We spent a lot of time in the nature exhibits on the main floor. Many of which have buttons you can press to either learn more or hear the sound of the animal. If you have a toddler, you know the allure of a button and I’m sure can understand why so much time was spent in this area.

We wanted to make sure we saw the dinosaurs. The most famous one is named SUE and is the largest and most complete T. rex skeleton. 

Walking up to the second floor where most of the dinosaurs are located, we could sense nap time was nearing. So, we tried to move through this section of the museum quickly, but ended up cutting our visit with SUE short due to a toddler meltdown.

What we ate in Chicago: Pizzeria Portofino (thanks to DoorDash) 

I made a late lunch/early dinner reservation at Pizzeria Portofino a week in advance. I was so excited. Between the pizza, pasta, Aperol spritzes and cute aesthetic, I had possibly found a new favorite restaurant. We even had a reservation on their heated patio. If you live in the Midwest like us, you’ll take any opportunity to be even somewhat outdoors in the winter.

Our son is currently in between the nap/no nap phase of life. If he has a jam packed day, he’ll need one. If we have a chill day, he doesn’t. Despite the three years of parenthood under my belt, I didn’t plan well and should have known that a day of trains and dinosaurs would put us squarely in the nap camp. Needless to say, we opted to skip our reservation and keep everyone’s sanity. But luckily for us, Pizzeria Portofino was on DoorDash (I could even order the Aperol spritz!). Lounging in the hotel room with our food actually ended up being the perfect way to spend the afternoon.

Overall, it was such a great trip to Chicago and was a good reminder that we should visit more frequently! If not just to make it the rest of the way through the museum and actually enjoy that Aperol spritz on the patio.

This post contains affiliate links, which means I make a small commission if you purchase using them. This commission helps me run my blog. I only ever recommend hotels and attractions that we have experienced and truly loved.