Chicago With Kids

Going to Chicago has been on my list since as long as I can remember. The beginning of the year we were in a rut of where to go with the kids and finally decided to just go for it! Taking our kids to a city is something we hadn’t tackled yet. It felt a little overwhelming, but we were excited to try! We stayed five days and took on as much as our kids would let us.  

We started our trip by going to the Crown Fountain. Our first day in Chicago was HOT, this was the perfect place for this kids to run and get some energy out. All while Tim and I were able to sit on the side benches in the shade and watch them play. 

Millie is wearing: 

Hair Ties (COMING SOON!) // Swimsuit   

Moses is wearing: 

Swim Trunks   

After the Crown Fountain we were able to throw on some swim coverups and go to The Bean! They are right next to each other so it makes for a good stop to check off two “must see” places. For us and our kids, The Bean was hot and crowded. This is totally just my opinion, but I would make sure to have a couple of places near the Bean to check out and not just go for that. You definitely need to see it, but I wouldn’t schedule for more than say, 30 minutes of it on your schedule. 

Millie is wearing: 

 Sunglasses // Dress // Shoes  

Moses is wearing: 

 Romper // Shoes  

If you don’t pay attention to anything in this post, pay attention to this: stay somewhere with an amazing view. Take whatever you would have spent on dinners and outings, and instead put it towards a room with a view. We had Moses nap in the stroller during the day, but by 6:30 our kids were done. They were so wiped out from the day that we had them in bed early! Every night Tim and I would order food from local places, buy a bottle of wine, sit back, and enjoy the view. Our AirBnb had to most incredible views with a balcony. We were able to put our kids down and still enjoy the city. To me, this is a MUST when traveling with kiddos! 

Our next day we had planned an Architecture Boat Tour. This was the kids first time on a boat, so they were super excited! Before hopping on the boat we stopped for Donuts. The boat tour is a great time to let the kids sit back and relax while everyone gets to see the city!  

Millie is wearing: 

Clip // Tank // Shorts // Shoes   

Moses is wearing: 

Tank // Shorts // Shoes   

The one thing we knew when planning this trip is that we needed to go see a Cubs game! Let me tell ya, it was just as magical as you would imagine. Being in this old of a stadium with all of its history is just something you can’t explain. We ate hotdogs, Tim and I drank cold beer. Our kids got every snack and treat that walked by us. It was definitely a favorite and I honestly don’t really even love sports. If you go to Chicago, seeing the Cubs has to be on your list! 

I’m wearing: 

Backpack // Maxi  // Shoes   

Millie is wearing: 

Swing Dress // Shoes  

Moses is wearing: 

Jersey // Shorts // Socks // Shoes   

I haven’t talked much about the food because well, we were hauling around a double stroller and have a two year old that won’t sit still for any restaurant, no matter how great. This ended up being the part of our trip that just had to give. If we went back without kiddos, we would eat all the things. The one place that I made a priority, and thank goodness I did, was Little Goat Diner. This food. That cinnamon roll. Best meal, hands down. I will be dreaming of making it back to Chicago for this restaurant alone for all of my days. After you stuff yourself, don’t forget to walk the two blocks over to Jeni’s Ice Cream! You have to make room for that. Trust me. 

Millie is wearing: 

 Tank Dress   

Moses is wearing: 


On the last day of our trip we decided to treat Millie, because she is such a trooper when it comes to being a big sister. The amount of times that she stopped Moses from crying or gave him her toy, are too numerous to count. Tim took Moses to a park nearby and I took Millie to the American Girl store! We kept asking the kids what their favorite part of the trip was and before this she would say “I like it all”. While walking around the store she grabbed my hand and said “Mama, now I know what my favorite thing is.” This store was pure magic for her. And Moses was able to get out his energy before our flight home! All around it was a win win.  

Millie is wearing: 

 Headband // Swing Dress (COMING SOON) // Shoes  

Moses is wearing: 

 Tee (COMING SOON!) // Shorts  

This trip to Chicago came with its moments. Trying to find the elevators to take the double stroller down to the subway, finding kid friendly restaurants, Moses screaming through a good part of the trip. But, it was worth every second. Traveling with kids can be hard! But allowing Millie and Moses to see the world is one of our top priorities. If you’re debating on taking your kids on a vacation, do it! It is worth every bit of memories they will make. Chicago was such a beautiful city for us! We can’t wait to make it back! 

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