Our Route 66 Adventure: Day 1 – Jeeping Through Chicago and Chowing Down on Chicken

Our Route 66 adventure officially kicks off today, and we’re ready to roll! We were checked out of the hotel by 9am and heading straight to the car rental at the airport to pick up our wheels for the next two weeks.

Atlas Stationers – A Pen Lover's Dream

Our first stop in the city was Atlas Stationers, a pen shop I’ve had on my bucket list for ages. It was thrilling to finally get the chance to pick up a few new pens and inks—though the reveal will have to wait until I get home. Spoiler: there’s some serious pen envy coming your way.

The Bean – More Than Just a Mirror

Next, we headed a few blocks down to visit the famous "Bean" (aka Cloud Gate) in Millennium Park (link: Millennium Park). I’ve been wanting to check it out for ages, and we found some street parking just a block away, right under the iconic "Beginning of Route 66" sign. Perfect spot for a quick photo op!

As we strolled through the park, we stumbled upon an amazing water fountain, and to our surprise, the bricks behind it were actually LED screens that change images—how cool is that, especially under the blazing sun?

The Bean itself? Well, it’s even more impressive up close. I reckon Wellington needs one of these! It’s a beautiful, interactive piece of art, and I could’ve spent hours just watching people and admiring the reflections. Definitely one of my favourite art sculptures I’ve ever seen.

A Local Feast

By this point, we’d worked up an appetite, so we checked out a food truck gathering nearby. Supporting local? Check. We found a lovely spot under some trees in the sun, watching people (and birds) while enjoying a great lunch. It’s the little things that make travel special, isn’t it?

A Stroll Down Memory Lane

From there, we drove through the old neighbourhoods of Chicago where my uncle grew up in the late ‘30s before heading to New Zealand. While we couldn’t get photos of the family homes (thanks, freeway construction!), the neighbourhood still has some of its old charm. It was a surreal experience, getting a sense of the past in a city that’s changed so much over the years.

Historic Pullman – A Slice of History

Next up was Pullman, a beautifully preserved historic district built by George Pullman in the 1880s (link: Pullman Historic District). Originally built as workers' housing for his railroad company, Pullman is now a national historic landmark, offering a glimpse into 19th-century industrial America. Lia went into the visitors' centre for more details while I took a quick 30-minute nap to recharge—jet lag is real, folks.

A Surprising Road Trip Find

After our nap, we made a quick stop at a local Walmart to stock up on road trip snacks, drinks, and tissues (because you never know). To my surprise, they sell even bigger cans of Red Bull here—591ml! I thought I was looking at a can of soup at first.

Route 66 Landmarks: First Stops

Our journey southward started with a couple of classic Route 66 landmarks:

• Castle Car Wash (link: Castle Car Wash) – Built in 1925 and designed as a castle, this spot was also rumored to be a hideout for none other than Al Capone. Yup, he used this place to lay low during his bootlegging days. Fun fact: he allegedly lobbied to have Route 66 paved to speed up the transport of his contraband liquor. So, if you see a castle-shaped car wash on Route 66, you’re definitely in the right place.

• Henry's Drive-In (link: Henry's Drive-In) – A Route 66 classic, Henry's has been serving up Chicago-style hot dogs since 1950. It’s a nostalgic stop, famous for its neon sign and hot dogs topped with fries. (Yes, it's a meal in itself.)

Dinner at Dell Rhea’s Chicken Basket

As the day wound down, we headed further south to Dell Rhea’s Chicken Basket in Willowbrook, Illinois (link: Dell Rhea’s Chicken Basket). Established in the 1930s, it’s a Route 66 staple known for its legendary fried chicken. After a long day of sightseeing, there’s nothing like biting into crispy fried chicken while soaking in the retro vibe of this iconic spot.

Wrapping Up Day 1

By the time we found our hotel at 5pm, we were ready to unload the Jeep, rest up a bit, and recharge for tomorrow. We grabbed dinner around 7pm, then returned to the hotel to update our journals and blog. Day 1 was a success—stay tuned for more adventures!Now we start to get into some of the Route 66 main stops as we start to head south out of Chicago