Chicago – Travel Adventures With A Toddler

Do you ever want to go on vacation and wonder if your toddler will enjoy it? I always do. If you have not seen part 1 to How To Travel With A Toddler, click here to see it. My son is a 4-year-old, hyper, and extremely curious toddler is growing up to be a very in tune with what he does and does not like. When I take my son on vacation with me, I have to constantly think about what he can handle as a kid. I say this because, he does take naps and he also eats like a racehorse. Where ever I go, my son travels with me. Let me just say, he is like most toddlers that throw tantrums, need to go to the bathroom at the worst times, etc. But that does not have to ruin our fun because, as you know, we are on vacation. At times, you may just need to step aside and take a break to talk to your toddler. It seems like communicating with my son really seems to help him gather himself and focus again. Here is part one of our Chicago vacation!

The Good Times Together

So I have said it, and I will say it again, we go EVERYWHERE together. A lot of times it is just that we just do not have the support circle available to others and baby sitters, that an entire different topic. Either way, my schedule always revolves around activities and places we can go to together. We took a trip recently to Chicago, where we spent a lot of time doing things that I know he would like but that I could also enjoy. When you are traveling with a child, I think it is important to not only thing about yourself and how you will enjoy your vacation but how they

Chicago Transit

will enjoy it too. The planning of that trip took a bit more effort since we would not have car and transportation is a must. He was big enough to ride the Uber or Lyft with me and at times we took the train or bus. We always used this as learning experiences. For example, we would make things fun by asking him “What are we riding on?” Or “Do you see a red car?” It was always something to look at and that kept him entertained while traveling around the city. Chicago, is a vibrant place! So there is so much to engage with. It was so much fun exploring the city with him

Be Local

When we stayed in Chicago, we slept at my sisters apartment which is not far from the beach and the park. Luckily, my sister has been in Chicago long enough to make some pretty awesome friends that invited us to the beach with them! We all met up and while my son had an absolute amazing time playing in Lake Michigan and building sand castles, I could not have felt more welcomed by a solid game of beach volleyball. I think that when you are traveling, it is great to look at things that are happening locally and when you are trying to
Chicago hot dog festival
find something that is more your style, Google is always my resource. During our stay, I Google searched “Chicago happenings” andguess what?! The Chicago Hot Dog Festival was happening that day! That was so much fun because they had things for children to do and, also, kids typically enjoy hot dogs. The other thing was happening the same week was the public screening of the Disney movie Coco. That was happening at Millennium park at sundown and we had so much fun! There were so many people there and we packed some snacks to enjoy during the movie. That was a fun experience and to top it off, it was free! Don’t be afraid to try some of the local things, not just going to the museums and tourist spots.

Adventure Awaits!

There are times when we go on vacation and think that we absolutely need to have a schedule but let me tell you, just enjoy yourself. I had so much planned We were walking to designated standing area when we were asked if we would like to get on the last boat of the evening, which was also heading out to see the fireworks. That was totally not in our plan but my son had never been on a boat, so I figured, ‘what a wonderful opportunity!” So we jumped on the boat that took us out onto Lake Michigan and we watched the amazing firework show. It was an adventure that I know we will cherish forever, especially because it happened on the fly!

The Children’s Museum

We finally reached The Children’s Museum and I can not tell you that it has been one of the best children’s museum I have ever been to. I’m sure my son Kids having fun at Chicago children’s museum will second that because he did not want to leave, even after 3 hours! If we did not have a flight to catch, I’m sure we would have stayed longer. There is so much to do here that I know you, as the adult, will also enjoy it yourself! Even just watching my son have so much fun and interact with other toddlers was great. They can learn so much from each other that they forget they are even learning. When we were finished, they had so many places to eat on the main floor. Mind you we are Navy Pier, where we had spent the evening before riding the boat, so my son immediately recognized the boats. We sat outside to eat our lunch and watched the boats go by. Navy Pier itself, has some great things to just walk around and look at. Before we left, we had gotten some souvenirs at the local shops that were around. There was something for everyone.

With That Being Said

Regardless of where you go, a vacation should be fun for you and your family. It is a time to enjoy and not worry about things. That has really helped me to enjoy our vacations together considering not everything will go as planned. There are some things that are out of your control and those things you should not worry about. It is good to have some ideas of what you would like to do and you can figure out how to execute it as you see fit. With that being said, I hope you have all happy and safe travels on your next vacation! I would love to know how you travel and if you try to do kid-friendly activities too. Don’t forget to tag me @ViVacation #FunTravelStuff


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7 thoughts on “Chicago – Travel Adventures With A Toddler

  1. HI Nikom thanks for your post.  We try and travel a bit and have our 7 yer old in tow.  It is so great that you were able to find things that were enjoyable for him as well as yourselves.  we were worried when we started traveling with him as we thought we wouldn;t be able to do the things we used to do – restaraunts, bars, long walks etc but we have found that there are so many things that he loikes that are just as much fun for us.  In fact it has opened our eyes to things that we would not have seen otherwise.

    Like you we used to try and schedule but to be hinest, we have found our best days have been when we have said to him “you can go here, here or here… which one do you want to do first?’.  

    Thanks again, I enjoyed your post and glad you guys had a great trip


    1. Hey Paul!

      Traveling with a kid is turning out to be fun and asking them where they would like to go first is an awesome way to engage! Thank you for engaging!


  2. Hello Niko,

    Thanks for sharing your adventure experience in Chicago. Things never always go according to plan, and sometimes you just have to make the most of it. It looks like you and your son were able to do that and have a blast at the same time. I’m glad you were able to experience how great the city can really be, especially if you go at the right time.

    Sometimes you can just be lucky and in the right place at the right time. I would like to see more pics of your adventures and I’m curious now to see what this children’s museum looks like. I saw a museum in Dallas that was pretty incredible and has many amazing exhibits that kids love. It is called the Perot museum in Dallas. 

    It is very much an adventure in itself when going there, as there are different paths you can take, including one with a diagonal glass box escalator that goes all the way to the top. I would highly suggest this museum as a destination if you and your son are ever in the dallas area.

    It seems like you know his habits and tendencies very well by now. I’m glad to see that you are able to spend alot of time with him. I look forward to hearing about your future adventures!

    1. Hey Daniel!

      I would love to go to Dallas and check out the Museum there one day! That escalator is something my son would definitely love. I’m working on gathering up the photos now and I will definitely let you know when they are up on the website. Thank you for stopping by!


  3. You had a great great time, I am sure. Traveling with kids is sometimes difficult. I remember when my kids were kids, now in their 29, we went many places and because they were twins was really hard to deal with every thing. Once my son took a  bag full of holes and went fishing with another boy, I was so worry, he didn’t tell me nothing. After looking on the shore the boy’s mother told me everything. It was a bad moment for me, but he enjoyed a lot.

    1. Hi Maria!

      What a scary moment! I, too, have a curious child that loves to wander. I only have one on hands so I can not imagine two. Thank you for your story!


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