Week 1: Cleveland – Chicago – Madison | Adventures in Travel Hacking

We left home pretty early on a Sunday and made it to Cleveland around 2pm. We first headed over to the Rock and Roll Hall of Fame on the waterfront. It was cool to see the artifacts from the artists, especially their costumes. It was really busy and one of our first experiences post-Covid in a space with a lot of people, so we all felt pretty anxious. After we left we headed down to the waterfront and almost got caught in a pop-up thunderstorm. We then checked into our hotel, Metropolitan at the 9, which we got for free with Marriott free night certificates. It was a nice big room with a sofa and wall fireplace. For dinner we walked down to Masthead brewery to meet my travel-hacking friend Jason. We tried some great wood fired pizza and local beers. After dinner my husband and I had an after dinner cocktail at the rooftop hotel bar and walked around a bit more.

The next morning my husband had some work calls so the boys and I drove out to the Tremont neighborhood and had breakfast at Grumpy’s. Afterwards we walked about 15 minutes to the Christmas Story House museum and bought tickets for the 10am tour. I should mention that it was crazy hot and humid! The tour was pretty interesting and gave a lot of information about the film, A Christmas Story. Only some scenes were filmed in that house and others were filmed in Canada, which was good because it didn’t snow in Cleveland for the whole time they filmed. They had to make do with foam and instant mashed potatoes! You are able to play around with all of the objects in the home as they are not the real artifacts, so the kids and I had fun recreating some of our favorite scenes.

Next we headed back to the hotel to pick up my husband and then we drove down to Cuyahoga Valley National Park, our first national park of the trip! We had read this national park is a little underwhelming as it is kind of woven throughout the suburbs of the Cuyahoga Valley between Cleveland and Akron. We went to the visitor’s center and talked to the ranger about some hikes we could do. It was super hot and extremely humid, so we weren’t sure how much hiking we had in us. We visited a little general store that is part of the park and tried some Ohio Buckeye candy. We drove first to Brandywine Falls, which was nice, but actually not as impressive as a lot of the waterfalls near where we live in Central NY. I suppose we are a little spoiled! We did a loop hike here and got pretty hot and cranky. Next we drove over to The Ledges, which is supposed to be a cool iconic hike through some rock gorges. It thunderstormed right as we got to the parking lot so we waited in the car until it stopped and then headed out. Thank goodness it rained and cut the heat and humidity a bit! The hike was pretty cool as the rock formations got pretty massive towards the end. The geology and landscape was actually very similar to where we live though, so it seemed like a fairly typical hike for us. Afterwards we headed back towards Cleveland and had an awesome German dinner at Das Schnitzel Haus!

Did I mention that my oldest son developed a cold on the first day of our trip? The kids have not been sick for 18 months between mask-wearing and social-distancing, and he got sick on day one. I was really worried he would give it to the rest of us, and of course, my other son caught it from him and was sick by day 3. So that morning he decided to rest in the hotel with my husband, and I took my oldest son, who was feeling better, back to the national park to ride bikes on the Ohio and Erie Canalway, which runs partly through the national park but also some state and local parks. On some days you can catch the railroad and do a bike and ride, but unfortunately the train wasn’t running that day. It was still incredibly hot and humid but did feel a little cooler in the shaded forest that we rode through on the canal towpath. We rode down to a cool beaver marsh and turned around. On the way back my son’s brakes locked up, throwing him off the bike. Luckily some strangers stopped to help us get the bike in good enough shape to ride back. We made it back and had lunch at a local chain, Winking Lizard.

We headed back to the city and all four of us walked through the city over to the Cleveland aquarium. It was cool to see some more of the city along the way. The aquarium was small but they have a really long tunnel with sharks! That evening we decided to get tacos from a place by the hotel, but unfortunately there was an Indians game and the place was packed! My husband and I waited at the bar and secured the food, which was really good. Then we packed up to head out in the morning.

The next day we started driving west to Indiana. It rained a lot along the way and we were really nervous our day trip to Indiana Dunes National Park would be rained out. By the time we got there the rain did stop and after a trip to the visitor center we headed over to Indiana Dunes state park which is kind of in the middle of the national park. We wanted to attempt the “3 Dune Challenge” hike. It was really cool to hike on sand dunes through the forest and peak at the top of the 3 dunes. You could see Lake Michigan. By the 3rd dune we started to feel some raindrops and it began to rain. We made it down to the campground and car and drove over to one of the beaches on Lake Michigan before heading to Chicago.

We arrived in Chicago around dinner time and just ordered food in. We stayed at the Residence Inn in the North River neighborhood on Marriott free night certificates. The kids were exhausted so once it got dark my husband and I went for an evening walk. We went down to the Chicago river and so many of the buildings were lit up in rainbow for Pride month. It was beautiful and I immediately fell in love with the city.

The next day we checked off many Chicago boxes: Millennium park and the cloud gate (bean) sculpture, the Field Museum, the Shedd aquarium, a water taxi to Navy Pier, and an architecture boat tour. Plus Chicago dogs for lunch and deep dish pizza for dinner! Everything was awesome! The Field Museum had an exhibit on one of my heroes, Jane Goodall. I read her biography last summer so it was really cool to see some personal artifacts. The aquarium was great, especially the beluga whales. I loved the architecture tour and would highly recommend this as a must-do for a first time visit to Chicago. I thought the Chicago dogs were surprisingly good and the deep dish pizza was ok, although I could only eat one slice. That night was watched Ferris Bueller’s Day Off, the classic Chicago-based 80’s film.

The next day I had some morning meetings and so the boys took a walk along the Riverwalk and found an awesome Cuban coffee shop. Once I was done I met them at the Willis (Sears) Tower so we could go up to the top. The line was a bit long but the view was amazing. Plus we got to stand where Ferris, Cameron, and Sloan did from Ferris Bueller’s Day Off. We waited in line to go to the plexiglass boxes that jut out from the building. I went on for about 10 seconds before I felt nauseous and got off, but the kids had fun playing around on them.

After we left the sky deck we walked over to the Art Institute of Chicago. Luckily for us they had the Obama Presidential portraits on exhibit! It was so exciting to see them in person! The AIC is huge but we wanted to see as much of it as we could, so we spent the rest of the afternoon there. By the time we left in the early evening, our feet were killing us, but we really wanted to leave the Loop and check out one of the outlying neighborhoods for dinner. We chose Andersonville which was historically Swedish but now is the LBGTQ neighborhood. We took the L there and it was a great choice. Nice, pleasant streets and a main drag with some cool shops and restaurants. We are dinner at am Irish pub, Lady Gregory’s, and got dessert at an Argentine gelato shop before heading back to the hotel.

The next morning we left early and started the 2 hour drive to Madison, Wisconsin. We got there just in time for the Saturday farmers market that is set up around the capital building. We grabbed some delicious iced coffees and then some lunch at a Venezuelan food truck (arepas), which was awesome. We walked around the market and state street and sampled and bought some Wisconsin cheese! Next we took a short drive over to the the free mustard museum in the neighboring town of Middleton. It was a cute place and we got to do a mustard tasting. Afterwards we headed back to Madison to check out the zoo, which is free! It was a great zoo with lots of exhibits. Finally we checked into the hotel, a Springhill Suites which was free on points, and enjoyed a swim in the pool. For dinner that evening we went to a local diner and then drove over to one of the parks on one of the lakes to watch the sunset. I really loved Madison! It was so pleasant and seemed like a great place to live! There were bike paths, lakes, and lots of free things to do and outdoor spaces. I would love to go back as we only spent one day there. That rounded out our first week of the trip!