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

After our first day on the road from NYC to Cleveland we continued on towards Fargo with the next planned overnight stop in the Windy City, Chicago. This was the easiest stretch of our road trip because the drive was only five hours.

Road Trip Day II: Cleveland to Chicago

We were concerned that the people of Cleveland and the travelers passing through were not taking COVID-19 as seriously as is socially responsible (lax on mask wearing and social distancing), so we were determined to leave early and avoid any other guests. We were in the parking garage and back on the road as the sun was rising.

WHERE WE STOPPED ALONG THE WAY

Angola, Indiana

• Lynette and I were surprised by the natural beauty of the farmlands of Indiana. It was a peaceful morning and we were surrounded by lush green and golden fields with only a few farmhouses along the way. Needing a good cup of morning coffee, we stopped about three hours into our drive at Five Lakes Coffee in Angola. I was disappointed that there was not a good selection for breakfast on the go (a handful of pastries). Lynette reminded me we were eating Chicago style deep dish pizza for lunch and to wait awhile longer…. The baristas were very friendly and helpful. We ordered our typical summer coffee, cold brew with oat milk. They were really good. Worth every penny. We drove on sipping our way into Chi-Town.

Chicago, Illinois

• Pequod’s Pizza with Caramelized Crust: As we drove towards Chicago, we were growing hungry. Very cleverly I placed our lunch order while on the road so that it would be ready for pick up at our arrival. I even grew nervous when we hit traffic that we would be late for pick up. As we entered Illinois my cell clock automatically set back one hour. New time zone! I hadn’t accounted for that. I would have to wait an extra hour to eat even though I had planned so ‘carefully’ to avoid a wait. C’est la vie. We drove up to Pequod’s and eagerly awaited our order for two deep dish pizza’s with caramelized crust. By the time the to go boxes were on our laps and we were headed to the hotel, the smell was a delightful torture for my increasingly growing appetite. Once we checked into our room (more on the hotel below), we dug into our deep dish. It was worth the hype and really delicious. I had the traditional cheese and sauce and Lynette loaded up on veggies and of course, shared with me. We both loved the caramelized cheese crust, it was really the star. Now, a lot of New Yorkers are upset by Chicago deep dish pizza and say it’s not really pizza. My opinion. It’s Chicago style pizza. It tasted great and it’s not supposed to be a New York slice or Neapolitan. It’s Chicago style and it tastes great.

• Staypineapple Boutique Hotel Chicago: Located in the Loop historic district of Chicago and just up the street from Millennium Park, this hotel is housed in 1895 skyscraper and designated a National Historic Landmark. It was the first skyscraper to have large plate glass windows making up the majority of surface areas. The hotel is has a very cool old Chicago vibe to it, with ornate floor tiles and stairways. The bar and restaurant are light and airy but closed due to the pandemic. Our view was great and the staff were wonderful. After checking in and enjoying our lunch we hit the city to do a little birthday shopping for my wife. Everything was within walking distance another great feature of this hotel.

• Chicago by Bike: When we returned from shopping it was still light and early in the afternoon so we took advantage of the hotel’s complimentary bikes and decided to explore some more of the city. We biked the riverwalk to the Cloud Gate and ventured to the Navy Pier. Lake Michigan was dotted with sailboats and kayaks, while we passed parks and sculptures on the other side. Hot and sweaty from our excursion, we decided to continue and bike to Aba for some take out dinner to bring back to our hotel.

• aba Mediterranean cuisine: located in Fulton Market District, we choose to get our takeout from aba because we wanted a lighter and delicious meal. While Lynette ordered a curbside frozen cocktail of sauvignon blanc, grapefruit, passion fruit and lime while we waited for our food, I decided to bike a couple of blocks to…

• Bonci pizza: for a few Roman style slices. Sold by the pound, Bonci pizza offers a wide selection. From the traditional cheese (my preference), to less traditional like onion, salmon and bufala, the choices are great. The pizza was really tasty. Light and airy crust with a nice sauce.

Winding down. As we biked back to the hotel, the streets had cleared and we enjoyed the wide lanes and stunning architecture of Chicago. We passed Marc Chagall’s Four Seasons Mosaic and stopped to enjoy a closer look. We enjoyed dinner at the hotel and a late night walk seeing the city by night. We went to bed exhausted from biking and walking the city in the June heat, happily full from delicious Chicago eats, and ready to rest before heading from Chicago to Fargo.