Carolyn Always Earley

Exploring Chicago in 3 days – October 2024

I recently traveled to Chicago for work and, although I’ve been there several times before, I’ve never actually toured the city. I decided to fly in a couple days early to visit family and see the sights.

Travel Day:

I flew into Chicago O’Hare Airport (ORD) on Saturday afternoon and took a taxi to my cousin’s place. He and his family took me to a great German restaurant called Himmel’s. We each had pretzel bread and beer (well, I had cider) while waiting for our meals. My cousin’s wife got the chicken schnitzel, which looked amazing but was huge, and I got the carbonara. (Not very German, I know, but I was really craving pasta!)

Day 1:

My cousin and his 4-year-old daughter took me into the city by train. I didn’t realize until I arrived that the Chicago Marathon was going on this particular Sunday and, unsurprisingly, the train was full to capacity as we reached downtown. We first wandered around the downtown area and checked out the Chicago Tribune Tower, which has very cool rocks from around the world embedded in it all around the bottom.

Our next stop was the pier at Michigan Avenue to take a River Architecture Tour. This particular cruise is my cousin’s favorite and, once I took a second tour the following day, I could see why. Thankfully, we had beautiful sunny weather and I was able to take a lot of great pictures while the tour guide told us about the history of architecture in Chicago and pointed out cool landmarks.

After the river tour, we walked to Robert’s for pizza (ironically, not deep dish). My cousin and I shared the caramelized onion pizza, which was SO GOOD. It was not what I was expecting but it was delicious! One of the great things around Robert’s is that they have a huge patio, so we were able to enjoy the weather and also watch a duck swimming around (I think that was his 4-year-old’s favorite part). Towards the end of lunch, it started raining even though there was no rain in the forecast – and then abruptly stopped after a few minutes. Apparently that’s normal there.

Day 2:

I took a Lyft over to my hotel, checked in and grabbed lunch with a friend at their NoMI restaurant. Their salted caramel espresso martini was great and so was the Caesar salad with salmon. We also had an incredible view of this building, which I initially thought was a church but later found out that is a historic water tower.

I took another river architecture tour, this time with my coworkers and on a boat called Chicago’s First Lady. This one was a bit longer (1.5 hours instead of 1 hour) and I liked it less than the other cruise for primarily 2 reasons (which were not the fault of the cruise itself): it was darker and colder, since we went at 5 PM. They did have great drinks on board, including hot drinks, so I was able to warm myself up while I took a few more pictures of the cool Chicago buildings.

After the tour, we walked to the iconic Giordano’s for dinner. This place was insanely busy and they have a unique process where you put your name in for a table and then get in line to pre-order your food. (We had a large party so we actually didn’t make it to the pre-order line, but I found that very interesting.) Their pizza is deep dish, pan or thin crust, so we tried a few different deep dish pizzas and one pan crust pizza (the margherita, which was so good).

Day 3:

On our walk from Giordano’s to the hotel, I learned about the Starbucks Reserve Roastery so I decided to check it out the following morning. Apparently, there are only a handful of these 4-story Starbucks around the world. The bottom floor was basically a gift shop; the second floor had a full, traditional menu; the third floor was labeled “experiential”; the fourth floor was a full bar (an actual bar with liquor and wine).

I went to the third floor (primarily because the line on the second floor was too long, but also because I was curious) and checked out their unique menu. I decided to try the Pumpkin Spice Whiskey Barrel-Aged Cold Brew and Prosciutto & Fontina On Cornetto. Both were delicious! I really wanted to try one of the affogatos (something I missed out on when I was in Europe) but that felt more like a dessert option.