That morning, we left for Chicago, about a 1-hour drive from Indiana Dunes State Park. We had time-sensitive tickets to another Frank Lloyd Wright wonder, the Robie House (See also our Falling Water Fiasco here.) This time we left 3 times as much time to get there as we thought we needed in order to be on time, and were still only about 20 minutes early…gotta love van travel and city parking. It was warm that day, so it gave me hope that we weren’t heading into an early winter after all and we would have more time in the Northern states than I thought. We have both been to Chicago a few times before and decided not to spend a lot of time there since we wanted to get to the places we’ve never seen before, much to the dismay of many friends and family that live in the area and wanted us to stop for a visit. Sorry guys!

If you need recs on some great Chicago places, take a stroll through Millennium Park, selfies at Cloud Gate, or more commonly known as the giant metallic “bean”, rent a bike and/or walk along the riverfront on Wacker Drive, explore Navy Pier and ride the Centennial Wheel for views over the city. Walk across the DuSable Bridge, and take a boat tour. We loved the architectural tour by the Chicago Architecture Center. If you need an indoor activity, visit the Willis Tower Skydeck, the tallest building in the Western hemisphere. On the 103rd floor, you’ll have amazing views of the city and beyond. Always end the day with a deep dish…more on our absolute favorite deep dish pizza later.

We took our tour at the Robie house and then had a few hours of coordinating my prescriptions and waiting for my New Jersey doctor to send my prescriptions to a CVS in Chicago. I won’t hijack this post, because I know the real reason you’re here is to hear ALLLLL about the mouth-wateringly delicious deep dish, but I could (and will) write an entire post (or many) about the woes of being a nomadic vanlife traveler with terrible insurance that only covers us 2 states….yes you read that correctly, 2 STATES!

Once my prescriptions were secured and we were free to roam the country for another month before having to coordinate refills, we rewarded ourselves with a famous Chicago deep-dish pizza, from our absolute favorite place, drumroll please……..Lou Malnati’s! If I had my way, I would have bought enough to fill every crevasse of the Travato fridge, but Humz said that would be excessive. So I only got one meat lovers for us to share. I have also heard of Giordanos, Unos, and Ginos being in the mix of crowd faves, and although we have only eaten Unos, once I bit into a Malnati’s meat-lovers, I knew the search was over. I seek them out every time I come to Chicago, and you can even have them shipped to anywhere in the country. (Don’t think I haven’t thought about this on numerous occasions. $116 for 6 pizzas is A STEAL!)

After the glorious pizza gluttony, some Lucy-care was necessary, and we needed to walk off our newly acquired pizza-weight, so we hit up Ohio Place Dog Park, and the more scenic Larrabee Dog Park, with views of the Chicago River. Humz’s favorite part of the night was when he spotted John Cusack and Bradley Whitford riding mopeds together as we left the dog park. How adorable!

Our 6(ish) hours in Chicago was coming to an end, as we started to make our way to Wisconsin, but not before one last sunset at Fullerton Beach and a roll-in-the-grass (for Lucy) with the city skyline as our view. Driving deeper into the Midwest, and more into the unknown, we weren’t sure when we’d see another major city skyline again.

Chicago, IL - Robie House by Frank Lloyd Wright

No trip to Chicago is complete without a Lout Malnati’s deep dish pizza!

View from Larrabee Dog Park: A sunset boat tour cruising along the Chicago River

Humz said this was 100% Bradley Whitford and John Cusack riding mopeds through Chicago. He also said John was on his way to pet Lucy if I hadn’t scared him away with my paparazzi cam.

View of Sears Tower/downtown Chicago from Fullerton Beach

Comet is gassed up and ready to take on Wisconsin! Goodbye Chicago!