From the skyline of NYC to the prairie lands of Fargo, ND and back again, this is my road trip travel guide on driving half way across the United States.

We had discussed extending our road trip by one day and splitting the drive from Chicago to Manhattan into two days. After a great morning in Chicago, by the time we hit dinner in Cleveland we realized everyone was ready for a night at home in Manhattan before heading to our final stop, the summer house in Sag Harbor. Happy with their electronic devices and a spacious car ride, the kids agreed we should venture into the night to arrive in NYC around 4:00 a.m. Though the kids slept most of the way, they woke up as we approached home. Excitedly they pointed to the Manhattan skyline as we crossed the bridge. As much fun as exploring can be, there’s no feeling like coming home.

Road Trip Day V: Chicago to Manhattan

WHERE WE STOPPED ALONG THE WAY

We decided the boys had to see a bit of the Windy City before continuing our drive because it was their first time in Chicago. We headed out of our hotel suite around 8:00 a.m. thinking we would walk to the nearby Millenium Park and Cloud Gate. My youngest son spotted citi bikes and everyone was quickly on board to take the city, with its wide treelined city sidewalks, by bike. We biked past some of the famous and beautiful architecture of Chicago, stopping for pictures. We went to the Cloud Gate (the “bean”) and enjoyed the gardens. On the way back to the hotel we stopped for some refreshment.

• Fairgrounds Coffee and Tea this coffee house serves nitro and cold brews on tap so you can more precisely select the type of iced coffee you’re in the mood for. We ordered the spy house and vinyl cold brew with oat milk. They were both excellent and our best cup of coffee on the trip. For the littles we grabbed some Honest Kids refreshers to cool down.

We packed up the car and headed back out on the road again. We stopped halfway to Cleveland for a little coffee and fruit smoothie break at Amanda Lee Coffee.

• Amanda Lee Coffee Fremont, Indiana

  The drinks were a tasty treat (with extra whip cream for the boys) and reprieve from the hot sun. My sons enjoyed tacking Seattle on the visitors board. NYC, with it’s small landmass, was already covered in pins. The service was very friendly and it was located in an Outlet Mall should you find yourself wanting for anything while on the road. Satisfied with our beverages we continued on to Cleveland.

• LJ Shanghai Cleveland, Ohio

  By the time we arrived in Cleveland we all had big appetites and were looking forward to getting takeout from LJ Shanghai. Known for their soup dumplings I ordered 4 rounds along with garlic noodles, soups, grilled shrimp, and spicy cucumber salad. We took our meal to Edgewater Park to enjoy the view of the city and our meal.

After our meal we were determined to continue until we were home in Manhattan. With a stop in Pennsylvania for gas and more snacks (and surrounded by a mass of flying evening bugs) we carried on until we reached our happy home at 4:00 a.m. ! Technically our road trip continued the next day from Manhattan to Sag Harbor, but with only 2 hours on the road we felt satisfied. My sons made it from the Pacific seas in Seattle to the Atlantic ocean in Long Island. The unusual circumstances of the pandemic certainly made 2020 a summer to remember.