Indiana Dunes and Chicago (Days 1-2)


Hi! My name is Charles, and I visited every contiguous U.S. state in the same trip. Learn more about me and my travels in "Road Trip w/ Charlie!"

Today, we're exploring the Indiana Dunes and Chicago!

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To provide some necessary background before we get into things, this marathon road trip that we’ll be diving into started out as just an idea I had while I was living in Michigan.

As such, the road trip technically started in Michigan — during a visit with my friends in the area, who graciously let me stay with them for a few days — but my numbering convention for the days only began once I left Michigan for Indiana.

Google Maps Directions From Ypsilanti to Grand Haven to Indiana Dunes

Interested in finding out more about how this road trip began? Feel free to explore more of our available articles from “Road Trip w/ Charlie” (listed in chronological order).

 
Indiana Dunes National Park Beach Seen From Hill

On the first day of the road trip, it hadn’t quite hit me yet. It’s one thing to come up with the idea to see every U.S. state in the same trip, but it’s another thing entirely to actually do it. I had tried to anticipate some of the challenges I might face beforehand, but as with most things in life, there are always things that pop up that you didn’t account for.

At this point in my life, I had never experienced sleeping in my car (out of circumstance or out of necessity, for which I recognize my privilege and make known). The evening of this first day served as the first true assessment of whether I was going to be able to make this dream trip a reality, and some quick adjustments were necessary (more on this later).

But, before the first night of the trip, I had less awareness of what lied ahead of me, and it was largely business as usual.

I began driving, and as I neared my destination, I encountered a train crossing in the middle of my intended path. If I was a superstitious person, I may have seen this as a sign of the long road ahead.

As I stepped outside of my car, I felt free and was extremely excited to begin this journey, with the first official stop on the trip being the Indiana Dunes!

Indiana Dunes Walkway Isometric With Dunes in Background

As with a number of the other stops on my trip, I chose the Indiana Dunes as a destination because they were located in-between some of the places on my list that I most wanted to see, making them a convenient stop in a state that I had less awareness of. Additionally, the Indiana Dunes contain a rich history as a National Park within the United States, and I was greatly interested in visiting as many National Parks as I could see during the trip as possible.

I never particularly considered myself to be “outdoorsy” before embarking on this trip, but as I began my hike through the designated walkways at the Indiana Dunes, I felt as though that aspect of myself might change.

I had chosen to start my trip at the beginning of April, and I was rewarded with a fresh, satisfying breeze at a base temperature in the mid 60’s that even Goldilocks would be proud of; not too hot and not too cold, but just right.

The sights along the path were beautiful, and the path took around an hour to reach the end at my leisurely pace. At the end of the path, I reached a sandy hill, which eventually led to a beach area, where I saw several people enjoying the nice weather.

Indiana Dunes National Park, Hill Overlook with Trees and Sand

From this beach area, the crystal-clear water reflected the sun’s gentle rays, making for a breath-taking sight to commemorate the beginning of this incredible journey. The clear horizons even allowed me to get a sneak peek of my next destination on the road trip: Chicago!

Indiana Dunes View of Chicago From Beach

Though the Indiana Dunes might rank fairly low on a list of my favorite National and State Parks that I saw on my trip, it is still definitely worth a visit if you ever have the opportunity, and it served as a great choice for the first stop on the trip!


Day 1 (Evening)

The evenings on my trip were largely uneventful when compared to the mornings/afternoons, consisting mainly of extended periods of driving and then scrambling to find the nearest Planet Fitness so that I could sleep in the parking lot and shower the next day.

But, for this first night, I figured it might be interesting to include a brief summary of how things fared early on, and I will likely write more articles on different tips/advice I was able to gather from these nightly experiences in my Travel & Destinations category on Couch Tripping.

As mentioned previously, the first night of the road trip served as the first real test for whether I was going to be able to stick with it through the long haul. When I left the Indiana Dunes, I knew that I needed to find a place outside Chicago where I could lay low and prepare for the evening. I found a Walmart parking lot about 15-20 miles from the city, and identified the nearest Planet Fitness where I could brush my teeth, wash my face, and change my clothes.

Google Maps Directions From Indiana Dunes to Chicago Illinois

Now, if you have ever been in a Planet Fitness men’s locker room, there is always that person that is scrubbing their face or shaving their beard or doing something else slightly out of the ordinary that gives others pause while they largely just change their clothes and go home.

For about two-and-a-half months, and across 40+ Planet Fitness locations, I was that guy. Sorry…

It was a bit of an adjustment to become less embarrassed by my need to do my personal care and showering in a public space, but over time I got more and more used to it. I think the hardest part about the evenings was finding a quiet place to sleep, and my initial sleeping setup was immediately found to be inadequate.

My first night was spent in a Walmart parking lot, which I had researched beforehand to discover was a place that road trippers frequently stayed at, as Walmart allows overnight parking at most locations. (Emphasis on “most.” Stay tuned for my Idaho update.)

Over time, I would find that simply staying in the Planet Fitness parking lots was an easy and acceptable solution as well. But, as the day started wane, and the sky grew dark, I noticed that the streetlights of the city were still quite bright. I made my way into the Walmart to find a sleeping mask that would help with this, but the only one I was able to find was meant for children and was about two to three sizes too small (which I did buy before realizing, and the discomfort wasn’t worth the minimal benefits).

I also quickly realized that the space in the backseat I had allotted for myself to sleep across was not large enough and I would have to sleep in the driver’s seat, leaning my chair back only slightly so that I did not crush the belongings I had placed behind it. With some windshield shades and magnetic blackout curtains on each window, I zipped up my sleeping bag in the driver’s seat and slowly made my way to sleep.

It took probably a few hours for me to finally drift off, but, thankfully, the April air was cool, which made getting to sleep a little easier. The next day, I woke, headed to Planet Fitness to shower, and then made my way to the next destination…

 
Chicago Skyline Seen From the Willis Tower Skydeck, Puma White Castle Shoes on Floor

Chicago! A city that likely requires no explanation of why I wanted to visit, I was excited to finally explore some of the things that I had always wanted to, such as Millennium Park or the Willis Tower Skydeck.

I parked my car in an underground garage and then spent the next couple hours just walking around the city, visiting shops, seeing the scattered sculptures/art, and getting a general feel for the city. The parking garage was near Millennium Park, so I also made sure to take my obligatory picture of The Bean.

Chicago Bean in Millennium Park, People Around, Man Blocking Shot

Once the Chicago Institute of Art opened for the day, I walked over that way to pay it a visit, taking in all of the incredible paintings and displays.

Mosaic Tile Arch in Chicago Institute of Art

Previous to my visit to the Institute of Art, my favorite artist was probably Vincent van Gogh. I am proud to say that after seeing some of his paintings in person, I think it is now Claude Monet.

Water Lily Pond by Claude Monet

Water Lily Pond by Claude Monet

After completing my tour of the museum, I looked for a local restaurant to stop at for lunch. I ended up eating at a seafood place named Brown Bag, which I cannot recommend enough. The delicious fish, paired with an assortment of vegetables and a drink they coined as Gingerade (a lemonade and ginger-based beverage), is a meal I think about very often and hope to eat again someday.

Brown Bag Seafood Meal With Fish, Coleslaw, and a Beverage

To round out my visit to Chicago, I stopped by Willis Tower’s Skydeck to see the city from up high. I was not disappointed.

Top Down View of Chicago Skyline Seen From the Willis Tower Skydeck, Puma White Castle Shoes on Floor

Being so high up in the air and walking out over the clear glass until you can see directly beneath you is such a surreal feeling. The cost of entry makes it prohibitive to do more than once, but it is definitely worth doing during your first visit to the city at least.

I had a lot of fun visiting Chicago (so much so that I ended up relocating to a suburb nearby after the trip), and these first couple days of the trip really helped set the tone for how the rest of it would end up going.

At this moment in time, I had yet to experience the road trip’s highest highs or its lowest lows, but I felt relieved in knowing that this goal might actually be achievable. With a head full of hope, I began my travels to Maquoketa Caves State Park in Iowa, which we will cover in the next installment of Road Trip w/ Charlie!

Google Maps Directions From Chicago Illinois to Maquoketa Caves
 

And that about wraps it up for this edition! For more information on each step of my journey, and to discover all of the places that I saw, feel free to explore the rest of my articles in “Road Trip w/ Charlie.”

Until next time, travelers!

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Charles Rarey

Charles is the founder of CouchTripping.com and is an accomplished writer with over 6+ years of professional experience. He enjoys teaching people about new topics, cooking, traveling, finances, and more.

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