CHRISTMAS IN CHICAGO
- Samantha
- Dec 30, 2024
- 4 min read
Updated: Apr 5
Dinosaurs, delivery for two (thanks, naptime!) and living the luxe life with a toddler in tow

Earlier this month, we spent the weekend in Chicago, and let me tell you -- sometimes a quick weekend trip with a toddler is the best and easiest kind!
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, but rather because my son absolutely loves trains and we could take a short Amtrak ride into the city. And let me tell you, it did not disappoint -- aside from the conductor not saying "all aboard!" when we boarded, as my son was hoping. He 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 this was a win-win for the whole family.
Westin Chicago River North: Toddler approved comfort, parent approved luxury
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 it did not disappoint! 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, so I'm not pushing a toddler bed. IYKYK. The hotel responded to my request so quickly, and even said they'd do anything possible to get us an early check in since we were traveling with a small child.
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 on the town. As if this all wasn't great enough, they gave us two bags of Garrett's Popcorn as a welcome gift which were consumed almost immediately.
Dinosaurs and fossils: The Field Museum was a must-stop for our little paleontologist
Dinosaurs might just be the only thing that can compete with trains for our son'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. I'd say we didn't even make it halfway through, 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 too have a three-year-old, you know the allure of a good button and I'm sure can understand why so much of our time was spent in this area.
We wanted to make sure we saw the dinosaurs -- the most famous of which 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 naptime was nearing, so moved quicker than a velociraptor on the prowl, but still ended up cutting our visit with SUE short due to a toddler meltdown.
When an afternoon date turns into delivery: Making the best of a tired toddler
I made a late lunch/early dinner reservation at Pizzeria Portofino about 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, and 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 very 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 GrubHub (I could even order the Aperol spritz!), and 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.
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