Louisville/Chicago Roadtrip 2026
In middle of August, my two younger sisters and I headed down to Louisville, KY for a few days and then we made our way up to Chicago for another couple of days of adventuring because our end goal was a FanExpo on Saturday night in Chicago to see the four Hobbits in the Lord of the Rings talk. We drove about 1400 miles and about 20 hours in total this trip. There were lots of memories made and good times to be had. *You can check out the photos of my trip in the Louisville/Chicago Roadtrip 2026 in Photos post to explore, if you would prefer.
We left Tuesday afternoon and drove as far as we could. We made a stop in Macomb, Illinois. Macomb is famous for the birthplace of Elizabeth "Lizzie" Magie, who invented The Landlord's Game (the precursor to Monopoly). If you head to downtown, there you can play a giant game of monopoly. There are painted squares along the sidewalks, even a Go to Jail square. There are sculptures the depict the top hat, dice and of course, Lizzie herself.
Wednesday, we arrive in Louisville, Kentucky in the afternoon. We make our way to the Louisville Slugger Museum. We were able to schedule a tour of the factory and even receive a mini bat at the end. It’s amazing how fast they can cut the bats with their CNC machines. It was neat to see that some players even request certain styles of bats or type of wood used for their bats. We got to see their cubbies. The museum they had was set-up nicely and it was great ready about past legends in the baseball world.
From there, we made our way to the Muhammad Ali Center. I enjoyed getting to know more about Ali’s past and how he stood up for what he believed in. He fought for the people. On the wall there were some quotes the Ali has said that if more people lived by them, this world might be a better place to be. One of the quotes was “Think well of all, be patient with all, and try to find the good in all.” Another one was “Inside of a ring or out, ain’t nothing wrong with going down. It’s staying down that’s wrong.” It was neat seeing a boxing ring and on the floor of the boxing ring they were playing video footage from Ali’s life. There was another part of the museum that had these seats with TVs where you could watch his fights. At the end you could walk down a couple flights of stairs and see his car, and what a nice car it was.
We made our way to our hotel, Homewood Suites by Hilton Louisville Downtown. This was a nice hotel to stay at for a couple of days. We decided it was time to explore downtown and get some food, so we made our way to Down on One Bourbon Bar. The food was good and the place had a really nice atmosphere to it. With food enjoyed, we wondered around the downtown and the architecture of the building was very interesting and cool to see. We found the Louisville Knot, which is an interactive sculpture and street furniture that can be used as seating, tables, a bike rack, and an extra-large swing. Throughout Louisville there are painted horses and we were able to see a few of them, of course I had to get pictures of them.
Thursday was an early start to the day. We had a tour scheduled at the Kentucky Derby Museum at Churchill Downs. I would say that this is what I was most excited to see in Louisville. It was nice being one of the first ones for a tour because our group was small and we were able to enjoy the museum without the huge crowds. We were able to head out to the track and see horses working out on the track. It was such a surreal moment being at Churchill Downs instead of looking at it through a tv. On our way back to the museum, we stopped by this wall of Post Position Winners, it keeps track of which post has the most wins. I can’t believe there have been no wins from post 17. It’s crazy. The museum was neat to walk through, the layout flowed well. There was a display of Cherie Devaux outfit she won the Kentucky Derby in and Golden Tempo with his Jockey in the Winners Circle with Roses draped over him. On one of the floors there was an exhibit dedicated to Secretariat, and his racing career. He still holds the records for the Triple Crown.
From there, we made our way to the Louisville Zoo. We were able to do a walk through a Wallaby enclosure; they are so cute. We made our way into the gorilla building, and they were some characters. There were these two that were so focused looking through the gate they kept getting lower to the ground thinking that would help them see better. On the other side, we saw a baby gorilla, and adorable. My favorites would have to be the meerkats, of course and the warthog, because Pumba, need I say more? It was a fun zoo to explore, and we saw lots of animals. Time for some supper at a place I’ve never eaten at before, Cracker Barrel. The food was good. I could eat there again.
Friday came way to fast, time to get on the road and head for Chicago! We arrived and made our way to the Griffin Museum of Science + Industry. In one area of the museum, you can see the Wright Brothers plane, while if you look toward the ceiling, you can see multiple planes hanging. A cool sight to see. You can even walk through a 727 Jet Mainliner airplane and see how a plane looks from the inside with clear panels to look through to the inside of the plane. There was a special exhibit happening at the time we were there, and it was the Anne Frank The Exhibition. We couldn’t take pictures inside the exhibit, but pictures weren’t needed. We all know the horrors that happened during the Holocaust. We get to see life for Anne before her family and her were captured. There was a replica of the Annex that they hid in along with their family friends. It was such a moment, that it was hard to take in. Hard to imagine what she went through, or how anyone could go through that. This exhibit was narrated through a device you had to carry, and you had to scan these buttons and the story unfolded from beginning to end about Anne’s life.
Another special exhibit happening we visited was Crafting Character: The Costumes of Paul Tazewell. This exhibit was set up so cool because he narrated while the walls played video and photos. So, every room you stepped into, he talked about his thoughts behind the creation of the costumes and how they came to be. My favorite costumes would have to be Hamilton. It was awesome seeing the costumes in person right in front of you. Seeing King’s costume was the cherry on top. In another room we got to see the Wicked costumes and the was cool as well, even though I have yet to see the movies. This museum was filled with many wonderful exhibits and science experiments.
We made our way to Millennium Park because you must see the Bean. I forgot how busy the park gets, holy people everywhere. We made our way to a new sculpture on display for a time, Reclining Liberty (3rd Edition), 2026; Flame of Liberty, 2026 by Zaq Landsberg. According to the plaque, “Lansberg’s work asks what happens when national ideals such as freedom, democracy and inclusivity are made physically accessible. By showing Liberty in a reclining pose, the sculpture suggests a moment of rest, change, or reflection. It invites viewers to think about what Liberty means today, and whether the ideals she represents remain upright and strong, are in jeopardy, or need to transform into something new altogether.” After taking in all the other artworks, we made our way to the Chicago Riverwalk long the Chicago River. Beautiful day for a walk, but so many people which is to be expected. We left the busy walk and headed for Michigan Avenue, which again so many people. We stopped by the Nike store, then made our way to the Harry Potter store where I got a tote bag of Doby, one of my favorite characters besides Sirius Black. My sisters asked me if I wanted to get sorted into a house and I said no need, I already know which house I’m in. Where’s my Hufflepuffs at? From there we stopped at the Starbucks Roastery. This place had a curved escalator that went up to the second floor, amazing. This place had 5 stories, insane. The pastries were good and I got myself a hot chocolate since I don’t drink coffee. After a day of driving and walking we finally decide to head to the hotel, Hyatt Regency O'Hare. Nothing like checking in at almost 10 o’clock at night.
Way to early on Saturday we made our way to the Shedd Aquarium, which we forgot that there was a Bears game, so naturally parking was a nightmare, and it just so happened to be pouring rain, what’s a 15-minute walk in the pouring rain? The Shedd was just like I remembered. The belugas were fun to watch with their trainers. We got to see some trainers take a couple of penguins for a walk and they were too cute. Thankfully the rain stopped for our walk to the Field Museum. Of course we had to go see the Ancient Egypt exhibit. Still on my bucket list of places to go see. It will happen one day. I got the see the Lion of Tsavo. On one of my favorite tv shows, Expedition Unknown, one on the episodes talks out the Man-eaters of Tsavo and how they impacted the building of a bridge in Kenya. They have the actual skulls of these lions. You can’t visit the Field without seeing Sue. So of course, I got a selfie of Sue and us.
We decided to stop by the Lincoln Park Zoo, many of the animals weren’t out for us to see because at the time there was an Air and Water show going on with jets, and the loud sounds scared the animals. But the animals we did get to see, was cool to see. We got to see a baby Zebra, which was adorable with the brown stripes. The lynx was neat to see when it decided to come out of its den. Even though we didn’t get to see many of the animals it was still a fun time with the sisters.
Fan Expo Time! I was so excited to see Elijah Woods, Sean Astin, Dominic Monaghan and Billy Boyd all together on stage. This is Cloey and my first time ever experiencing a Fan Expo and let me tell you I was not ready. Wow. The amount of people and the people dressed up as their favorite characters was lot to see. I am a huge fan of The Lord of the Rings and it's celebrating its 25th year this year. Seeing these four on stage talking and laughing and just having a great time was awesome to see. You can tell the friendships they made 25 years ago are stronger then ever today. They had to blind taste three different Chicago Dogs from three different restaurants and say which place was better. I am not a fan of the Chicago Dog, no thank you. They had the audience laughing with a skit they had to perform as Star Wars characters. Thankfully our hotel was a five-minute walk after we figured out how to get of the craziness of all the people.
Sunday comes and we make our way back home. This was a fun trip and I’m glad of all the memories that were made with my sisters. Another place checked off my bucket list, many more to go. I can’t wait to see where we head too next. Once again I took too many photos, so if you would like to look at many of the photos I took of our trip, head on over to Louisville/Chicago Roadtrip 2026 in Photos post to explore.
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