We had a week to get to NYC, so timing was everything on this road trip. We left our Airbnb in New Prague shortly before 7am. The sun had been up for a while already, although you wouldn’t have guessed it from the gray, sleepy light. The empty, flat road stretched ahead—an early sign of what awaited us in Minnesota.
good morning from the road @New Prague
Our first travel day was set to be our longest stretch on the road. At least, that was the plan. Since we hadn’t found much to do in Minnesota, we were eager to cross the Mississippi into Wisconsin, grab something to eat along the way, and then push on all the way to Chicago. About 90 minutes into the drive, we crossed the Mississippi River at La Crosse, rolling over an old, industrial-looking bridge painted in blue.
Mississippi Crossing @La Crosse
After breakfast at The Root Note, we headed to Grandad Bluff, which offered an extensive view of La Crosse and the Mississippi River Valley. I had expected more from the view, but I was happy to stretch my legs and get out of the car for a bit. Grandad Bluff was used as a place of worship by missionaries starting around 1850, but Indigenous peoples had long settled in the area around La Crosse.
Before any European missionaries arrived, the area around La Crosse—including Grandad Bluff—was home to the Ho-Chunk Nation amongst others. The bluff and surrounding river valley were part of their ancestral lands, providing vital resources and serving as a place of gathering and cultural significance. When missionaries began using Grandad Bluff as a place of worship in the 1850s, it marked a period of cultural disruption for local tribes, as settlers moved in and traditional ways of life were increasingly threatened. Today, Grandad Bluff is recognized not only for its panoramic views but also as a reminder of the region’s layered history.
part of La Crosse and the Mississippi River Valley @Grandad Bluff
Next up we found Ripley‘s Believe it or not! in Wisconsin Dells as being along our route. This supposedly classic quirky roadside attraction turned out to be completely uninteresting. However, we did take a walk along the Wisconsin River, which looked impressively grand despite being tamed these days by 25 hydroelectric dams. With more time on hand, I think a river cruise might actually be worthwhile. Overall, though, Wisconsin Dells felt rather bland; even our coffee stop ended up being just a quick bathroom break. The place simply wasn’t as inviting as we’d hoped.
all ready for a river cruise @Wisconsin Dells
a mighty fine river @Wisconsin Dells
We bypassed Madison, the capital of Wisconsin, and drove straight to Chicago. It was still about three hours away, but we figured we’d arrive in the early evening and have time to see at least “The Bean.” Officially called Cloud Gate, it stands in Millennium Park and is a massive public art installation made of polished stainless steel. Its mirrored surface reflects the surrounding skyscrapers and visitors, creating a fascinating and ever-changing outdoor sculpture to explore.
here we come @Chicago
We parked right underneath Millennium Park and its Cloud Gate for the astonishing sum of $39 for the first three hours—a real bargain, if you ask me. On the bright side, we were literally steps away from “The Bean,” and since it was the only thing we planned to explore in Chicago, we figured we might as well pay a premium for a prime parking spot. Sometimes convenience really is worth the price.
The Bean @Chicago
the inner workings @The Bean
Since we had already paid for the parking there was no reason to leave Chicago in a hurry. Instead we checked what rooftop bar was available with a view on The Bean and eventually headed to Cindy’s Rooftop.
Since we’d already paid for three hours of parking, there was no reason to rush out of Chicago. We checked which rooftop bars offered a view of The Bean and eventually made our way to Cindy’s Rooftop. The spot turned out to be the perfect place to unwind, with sweeping views of Millennium Park and the downtown skyline. Sipping a drink while watching the city lights come on felt like the ideal way to end our brief but memorable visit to Chicago.
sunset mood @Cindy’s Rooftop
The view from the bar was definitely worth the price, and we were even allowed to bring the teenagers along. That’s not always a given in the U.S. We’d have quite a different experience with that as our trip went on.
Cloud Gate and Millennium Park @Chicago
We left Chicago after dark, the skyscrapers glowing in rainbow colors as if sending us off with a farewell show. There’s definitely more to explore in this city, but I was glad we had managed to see at least this one iconic spot. Leaving Illinois behind, we crossed into Indiana. A state we would come to know all too well over the coming days. But for now we were only looking forward to reaching Indiana Dunes. Yours, Pollybert
Millennium Park at night @Chicago
