Family Bliss On The Go to Chicago
If you are near the East Coast or Mid-Atlantic States, I would strongly suggest a weekend trip to Chicago some time. You can do this in a very inexpensive way, and my kids really enjoyed the city. They liked that it was a big city but with more "chill vibes" than NYC. Read below for our itinerary, what we would do the same or different, and some other ideas of things to do if you go to Chicago with kids. We took our kids in August 2026 (8yo and 11yo boys).
We stayed at the Congress Plaza Hotel. This was a less expensive option, and was great for location. Many of the sights we saw were within walking distance to this hotel. It was clean and just what we needed, but it is a no frills option, so keep that in mind if you prefer a nicer hotel. They do not offer free breakfast, but you can buy breakfast at the hotel's restaurant OR you can opt for what we did and walk a block to a nearby Dunkin Donuts.
We woke up and went to see the Buckingham Fountain first. It is basically right across the street from the hotel, and it holds a special place in our hearts because it is where Jon proposed to Beth.
We then walked along the water a bit, teaching the kids about the Great Lakes while they saw Lake Michigan, and headed to "the bean" in Millennium Park. It's funny because when we described where we were going to our kids, they were less than excited, but this topped both of their lists as their favorite thing in Chicago. If you don't know, it's essentially a giant silver/metal statue that is in the shape of a bean. What is cool about it for kids is that you can find your reflection in it, see yourself getting closer to it, and then stand underneath of it and see multiple of yourself (we counted 8 at one point). Our kids could have spent a very long time here, giving themselves high fives and making faces at their reflections!
Right near the bean, there are other artworks to see, including fountains that are giant faces on screens (if you bring spare clothes or at least crocs/spare shoes, you can splash in the giant puddles between the fountains) and just recently an additional statue of liberty laying down.
We then got into our car and drove to the Lincoln Park Zoo. This was about a 15 minute drive. If you have the time, you could do this on a separate day and stop at the beach or Navy Pier on your way to the zoo. Our kids were kind of sad driving past those and not stopping! The Lincoln Park Zoo has been FREE to the public since it first opened. You would think it's a very small or substandard zoo then, but it's really not. We enjoyed walking around this zoo a lot, and they have several different educational programs each day (check the schedule on their website to see what you can catch during your visit- we watched a program on ape cognition at the chimpanzee exhibit).
After the Lincoln Park Zoo, we drove to the Obama Presidential Center, which just opened this summer. We were lucky enough to secure timed tickets, but you need to definitely reserve these in advance if you want to go into the actual museum/center. However, there are many things you can visit for free on the grounds if you cannot get a ticket- check out the website for all the details. The museum/center has a lot of educational displays for kids, not just about Obama's presidency himself but a lot more about the history of our country and democracy. We were also fortunate to find free parking on a side street just a block or two walk from the center!
We drove back to the hotel to relax for a bit in our room before heading to a concert, which was the reason we were in Chicago in the first place. That evening, we returned to the Buckingham Fountain because my son wanted to see it lit up at night. Heads up, it stops running/closes at 11pm so be sure to get there before then. The kids LOVED the lights on the fountain at night....it topped my older son's list of favorites. Also, if you're visiting the fountain, it goes very high on the hour every hour for the first 20 minutes....but it also does so for the last full hour at night.
Other things we would have done if we had more time: Ghiradelli on the Miracle Mile for ice cream, the Navy Pier and/or beach, the Anne Frank Museum, and the Field Museum which was advertising a Pokemon Fossils exhibit right now. Jon and I previously have gone up to the top of the John Hancock building for dinner, but you can also make reservations/buy tickets just to go up the top for the look out with kids if you choose.
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