3 Days in Chicago with My Kids

I wasn’t able to send out a new note last Sunday. The week before had been the kids’ spring break and I was the solo parent with them on 6 days of travel so there was just no time to write. We flew to Chicago for the first part of our trip and stayed there for 3 nights. I picked Chicago because it is the start (or the terminus depending on which way you’re going) of Amtrak’s California Zephyr train, which is what we took to get back home to California.

The train ride took 53.5 hours, and I will devote an entire post to this bucket list travel item soon but I wanted to share a rundown of our time in Chicago today.

Even though it rained every day and snowed on our last day, we had a great time exploring Chicago and could have easily stayed an entire week without running out of things to do. There were so many museums to pick from but I allowed us to choose just 1 destination each day so that we could also see friends, enjoy the comforts of our hotel, and just immerse ourselves in the surroundings and energy of a big city. 

I love traveling with my children because of how easily excited and occupied they are. I have learned there is no need to overpack the itinerary. Some of the highlights of their trip was counting the floors of all the tall buildings they saw, getting to pull the cord on the bus for our stop, getting to carry their own umbrella, or being allowed to ride the elevator in the hotel alone without me. I find their simple eagerness so delightful, and it makes me see a different purpose for travel.

On our first day, we took advantage of the only few dry hours we had over our entire trip to visit the play area in Maggie Daley Park, the northeast corner of Millenium Park that has a multitude of recreational offerings. I was hoping to take lots of photos at The Bean, which was on the way, but it was unfortunately fenced off for upgrades. Still, there was so much communal green space throughout the park, and I could easily imagine how glorious it would be to hang out there on a warm, sunny day. 

After seeing friends for lunch and then swimming with them at our hotel, we took the public bus to the Shedd Aquarium. Our timing was a bit off and we ended up there just 1 hour before closing. Even though we didn’t get to see as much as we would have liked, we also got a lot of the aquarium to ourselves as it emptied out. It was my first time seeing beluga whales, and it felt magical to be staring at these large swimmers gliding through their huge tank without other humans around. Unfortunately, my reverie was broken when I realized my kids had disappeared elsewhere and I spent 2 nervous minutes trying to find them.

We ended the evening with a bus ride to our dinner destination, a Japanese BBQ restaurant where the kids got to grill their food and make s’mores at the dinner table. It was then a rainy walk home where Charlie of course announced that she needed to pee 2 blocks from the hotel. We raced back under our umbrellas and luckily ended up accident-free back in our hotel room.

The only items on the agenda for the next day was The Field Museum, a natural history museum, and a trip to the Hyde Park neighborhood to visit our good friends. The Field Museum is best known for the skeleton of Sue the T-rex, which is the most complete Tyrannosaurus rex in the world. The kids all wanted to see a 3D movie about Sue, and while I thought Charlie was too young for it, I knew the older kids would get a lot out of it so we went. My suspicions were right – the kids had never seen anything in 3D, and the subject and the 3D dynamics of this 20 minute show was a lot for Charlie, who ended up scared and in my lap as Sue fought and maimed other dinosaurs like she was in the theater with us.

When we finally entered the hall with Sue’s skeleton, she burst into tears and asked to leave right away, disappointing the other kids. We ended up spending the rest of our Field Museum time in the much gentler Hall of Gems and Naturewalk, filled with displays of taxidermied animals and birds. This was the one moment in our trip where I really wish I had another adult with us. With an almost 4 year spread across the kids, they are all at different developmental stages for how they could and wanted to experience a museum and another adult guide would have made the visit more enjoyable for everyone.

After just 2 hours, there was still so much to see but hangriness set in. I may have (i.e., I definitely) yelled at my children in front of a classroom of kids on a field trip but hunger and impatience got the best of me. Luckily there was a homestyle Italian restaurant right by our hotel, where the kids dug into heaping portions of pasta and chicken parmesan after I apologized for my bad behavior, and I inhaled a delicious Italian beef sandwich (after watching and loving The Bear, I couldn’t leave Chicago without eating one). If you’re ever looking for a good, simple Italian meal in River North, I highly recommend finding Bongiorno’s Italian Deli & Pizzeria. It’s located in the lobby of a big building (405 N. Wabash) so it’s a bit hard to find but the food was really good. We didn’t have room to try the pizza so I guess I’ll need to plan another trip to Chicago.

We all felt much better with our bellies fortified and after a brief break back at the hotel, headed out to see our friends in Hyde Park. We went with them to pick up their 3YO from daycare, took advantage of their washer and dryer to do some laundry before our long train ride, and enjoyed a huge spread of takeout from a Chinatown restaurant. The kids happily played while the adults caught up with one another; life doesn’t get much better than an evening of good company and good food. 

Unfortunately, our evening ended with Bowie throwing up his chicken parmesan in the lobby of our fancy hotel. His tummy wasn’t feeling great at dinnertime, and it all came up as soon as we got out of our rideshare and stepped foot inside. I have never experienced such kindness from strangers. I understand that it was their job to be nice to us, but they went above and beyond with how sympathetic and helpful they were. Brandon the bellhop rubbed his back as he heaved out his lunch and told him to just get it all out and Eden, a member of the housekeeping staff, made sure we didn’t worry about the mess. I felt terrible and went back down to thank them again after I got Bowie settled into bed. Brandon told me, “I have 7 kids and 13 grandkids. I’ve been there.” Being a parent has so many difficult moments but at least you know that every parent is bonded through the shared experience of those difficult moments. 

Luckily Bowie woke up the next day feeling just fine. We visited the hotel pool one last time to make sure we got our bodies moving before boarding our train at 2. All of us were sad to leave Chicago but we were very excited for the next leg of our spring break journey!