30 Day Road Trip: Chicago, Day 10

Chicago has a lot of family friendly fun to offer! How we spent a day, plus some advice for parking, toll roads, and low cost accommodations.


So here’s what’s going on: I am on a 30 day road trip with my kids, and we have had a number of stops along the way. Find our whole itinerary here. Our first stop was Fort Collins, CO. Our second stop was Nebraska. Our third Nauvoo, IL. And our fourth Chicago, IL, which I am sharing today.

In these posts I am sharing our travels, some tips and tricks I have learned while traveling with my four munchkins, and a whole lot of fun! So check it out because I am letting you know where we visit, what we eat, and where we stay. And how we do it all on a budget.

Navy Pier is a fun stop on our 30 day road trip across the country!

Navy Pier, Chicago, IL


It is one of my favorite cities, but I haven’t visited it in nearly 13 years. And this was the first time I have brought my children. I had BIG plans for this city. But made a silly mistake. Instead of taking the train into the city from where we stayed as I originally planned, I decided to drive. No big deal if you are willing to pay for parking, which I was. I have little ones, and that usually means needing “stuff” so I didn’t want to get stuck without something, so we drove.


I had my cargo carrier on top of my car, which made it too tall for pretty much every parking garage in Chicago. Which meant our plans changed quickly. I was able to valet park at Navy Pier, and that allowed us to have a lot of fun. But we had to leave before the valet did, so we had limited time. Everywhere else we planned to see ended up getting tossed when we couldn’t find suitable parking. Eventually we gave up, went and got yummy food, and went back to where we were staying. So my first tip is when visiting Chicago, park on the outskirts, or leave your car at the hotel, and take public transit in. It will save you a bundle in parking fees, and allow for a lot of flexibility and more fun.


But don’t worry about us, we still had an amazing time. Navy Pier has so much to offer, and we took full advantage.

We started with an amazing lunch at Riva’s. It is a fish house, and I ordered a lobster roll. My son got snow crab. My sister, a steak sandwich. Uh??? What??? Haha but that is what she wanted. It was all very yummy. And we got to validate our parking pass there, so instead of $33 for valet parking, it was $15. Which was nice.

Then we walked around on the Pier. There are boat rides out onto the lake, there is a ferris wheel, carousel, and other rides. Lots of places to eat. Great views. And a fun atmosphere.


My kids loved watching all the different boats go by, including the fire department. And they loved posing for a gazillion pics on all the cool stuff on the Pier.

At one point Derrick dropped his flip flop off the edge. Whooops. I was not happy. But luckily there was a little ledge thing (hard to explain) so Dillan gallantly hopped over the rail to retrieve the flip flop so it wouldn’t be lost to Lake Michigan.

dillan-chicagoAt that point I thought it would be safer to try something else. So we went to the Chicago Children’s Museum.

I have to say, I LOVE Children’s Museums, and can’t wait to share my post about the one we visited in Indianapolis, which is the world’s largest. But I have a special place in my heart for the Chicago one. It is the first I ever visited. 13 years ago. When I was a nanny. And it was all that I remembered and more.

My kids had so much fun, and were sorely disappointed when it closed. It closes at 5 pm, most nights, so go early so you have enough time to enjoy all it has to offer. If you are there on a Thursday, they have FREE family nights from 5-8 (of course this might change, so check their website)!

There was something for each of them, from a little town where the kids can put gas in their car and change tires, grocery shop, etc. to a fire station, water works, and more!

children-museum-chicagoOne of their favorite parts was the art projects. They got to attend a little class in a studio and make stuffed animals and pillows. It was fun to see how different each kid’s creation turned out.

They also got to mold clay, play in boats, and just have fun! Honestly, I wish we would have gone sooner.

children-museumWhen the museum closed, we decided it was time to get some food! Of course, we had to head to West Town Bakery for Doussants (Croissant, Doughnut cross). It is located at 15 East Ohio Chicago, IL and it is right by the ACME hotel. It is tiny, so you might overlook it, so just know it is there!

And try these delicious things. They had smores filled, birthday cake, and almond blueberry when we went and we got all 3 kinds!

west-town-bakeryThen we had to get Chicago dogs, and the place to do that for us was Portillos. It is on 100 W Ontario St. in downtown Chicago. I wolfed my hot dog down so fast I have no photo. But just know, that pickle, tomato, onion, and relish makes those hot dogs something amazing!

You guys, we had deep dish too. Which I could eat daily I like it so much, but my kids, who have only ever had “regular” pizza were thrown off by the cheese being under the toppings! Haha. They ate it and enjoyed it. But they were ready to try something else. Now, I wouldn’t dream of telling you where to go for your deep dish as everyone has a favorite and they are all the “best”, so I just say, make sure you try it!

PicMonkey Collage

We tried to visit Millenium Park where there is the “Bean” and the Fountains, and so many other fun, free, and cool things to do and see. But parking really was an issue for us.  But just know, Chicago has a lot of free options for family fun, as well as paid. Two such options are:

Maggie Daley Park.:  337 East Randolph Street, Chicago
Lincoln Park Zoo.  2001 North Clark Street, Chicago, IL 60614

Both are well worth visiting. And free. Plus very entertaining. I hope you can get to Chicago and enjoy some of the fun, food, and city life it has to offer. We only spent one day there, but we had a blast!

navy-pier2Because Chicago hotels are so expensive we opted to get an AirBnB for our stay in Chicago. The host was really nice. And it was really comfortable. Totally saved us a bundle, as we paid less than $100 a night rather than well over $200 for a hotel. It did mean being a little further out of the city. If you are going to use AirBnB check the location well, read the reviews left by others, and know what you are getting. We had a great experience with it in Chicago!

Another thing to keep in mind is that driving near Chicago means toll roads. So have cash so you can pay the tolls. My kids were blown away by this. Apparently because we live in a state that literally has no toll roads I know of, they had no idea they even existed, and every time I stopped to pay a toll they were like, “What? Why do you have to pay?” it was cute the first 10 times. Haha

Anyway, check back tomorrow for our next stop: Indianapolis! We did so much in Indy I had to break it up into several posts! But trust me, they are fun!







About Rachael

I am Rachael, I have a passion for all things travel. I have an incurable wanderlust, and a need to see and do. I have four littles that call me "mom" and I am currently wading through the ever changing tides of parenting. I am figuring out what works, and what doesn't. And, I have a passion for food. In fact, I have an entire website dedicated to food www.eazypeazymealz.com. I love to eat, cook, and try new things.

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