Travel Organization: Chicago with Kids


Chicago has held a special place in my heart ever since one of my best friends in high school moved away here. Taking the train by myself when I was 15 to go visit her ignited fond memories of the city which only grew with many trips back in the 20 years since. It was fun to take my kids here for the first time. We spent 3.5 days and 3 nights in Chicago with our 6 and 3 year olds and here is our experience.

what we did

Sadly The Bean was under construction so we could not get close, but it was fun for the kids to run around Crown Fountain even without the water on. And we’ve had requests to go back to the “faces” since.

A highlight for our kids. This park is HUGE and it’s easy to lose sight of your kids but a blast nonetheless.

Any place with a lot of options that is not a sit-down restaurant with kids receives 5 stars in my book. Plus it was delicious food. 

A highlight for the whole family. We spent 3 hours at the aquarium and ended up having an easy lunch there. We saw so many different types of sea creatures, touched starfish and watched a dolphin show. 10/10

  • Maggie Daley Park (again)

The kids’ request.

Before Maggie Daley park visit #2, we placed an online order for pizza to swing by and pick up after the park. This was a great call given it was PACKED. We ate pizza in our PJs at the hotel while watching Nickelodeon. Something we do not do at home!

I loved this and wish we could have taken our time in the immersive walk-through at the beginning. Unfortunately, our kids were tired and grumpy which made the experience less than pleasurable. If we brought our wagon I think it could have gone a little smoother but I was worried about checking it (it would not have been a problem).

Another favorite for the kids — and my hubby and I gave ourselves “best parent awards” for taking them and handling the chaos.

Thankfully there were a lot of easy food options post children’s museum in the same building at Navy Pier. It was dinner time and busy but did not take long to get our food or snag a table. We enjoyed chicken sandwiches and hot dogs.

where we stayed

We opted for a suite downtown at the Residence Inn over a hotel with a pool and I am glad we did because downtime at the hotel was needed. The only problem with this hotel is that there was not a door between the bedroom and living room/kitchen but luckily it wasn’t an issue with the kids being so tired. We were about a half-mile walk from the train station in one direction and a half mile to Millenium Park in the other direction.

how we traveled

We took Amtrak from Ann Arbor and I 10/10 recommend. We lucked out with seating for 4 with the tables between us both there and back and it was easy for the kids to stay entertained and move around as needed, and the bathroom wasn’t bad at all! We would take the train again.

Around town, we had our Babytrend Stroller Wagon and we would not have survived this trip without it. We could pile our luggage in it, or the kids. Both kids fell asleep on our walk home from the aquarium! They were content hanging out in it and could color or entertain themselves, look around, or eat snacks. This prevented them from getting overtired. All the places we went were wagon-friendly. I added clips, and a floor mat for ease of use. And would also consider netting on the sides for sweatshirts and a blanket. I wish we bought this when my son was born instead of a double stroller (it comes with a car seat adapter). This thing is much easier to navigate and is great!

other recommendations

Activities we’d check out if we went again or had more time:

Packing tips

Share this post

Picture of Ashley Tauscher

Ashley Tauscher

A goal in my life is to leave people and places better than when I found them. I provide personalized one-on-one services to simplify homes to help life run smoother, and photos to enjoy the memories made along the way.

Scroll to Top