A (Literal) Train Wreck in the Windy City

Fun Fact: A train hits a car every three hours. Our train was no exception.

Cindy’s Rooftop at the Chicago Athletic Association Hotel

A short trip to Chicago deserves a short blog post about the sights that were seen and the bars that were hopped, especially since the last time I visited the Windy City I was fairly young and only recall going to the American Girl Doll store. My aunt and uncle planned this trip as a surprise for my cousin Tony’s 21st birthday. Twelve of us woke up early Sunday morning (that 2:45am alarm was rough) and with our luggage, snacks, and some alcoholic beverages in tow, we were ready to embark on the train ride to Chicago.

After disembarking the train, gawking at how beautiful Chicago’s Union Station is (get it together St. Louis), checking in to the hotel, freshening up, and grabbing a quick bite at Jimmy Johns, we were ready to begin the birthday celebrations. Our first stop was Cindy’s Rooftop which is located at the Chicago Athletic Association Hotel. We took advantage of the unusual 50 degree December weather and sipped our drinks on the terrace which overlooked The Bean, Millennium Park, and Lake Michigan. After taking in the rooftop view and snapping a few pictures, we walked through Millennium Park and the Navy Pier until we stopped at the Billy Goat Tavern for a few beers.

When in Chicago, a deep dish pizza must be eaten. Heading back to the hotel to change, we decided to have dinner at Giordano’s. Each deep dish pizza at Giordano’s takes around 45 minutes to prepare. We placed our order in advance and stood around the bar until our table was ready. The restaurant was constantly bustling with people waiting for tables or trying to put orders in. The bar was not terribly packed and even though we were standing while drinking and chatting with each other, the wait for our table did not feel long. Though there were twelve of us, we were unable to finish off three delicious deep dish pizzas. My favorite was The Special stuffed with sausage, mushrooms, green peppers, and onions which paired nicely with a Bloody Mary. I also attempted a cheese pull, but I did not do it justice.

Apex Predator Farmhouse Ale at Dublin 4 Irish Pub and Cafe

With full bellies, we walked to Snickers Bar and Grill for some cheap beer. Since we all had woken up ridiculously early for the trip, the group broke up throughout the night to head back to the hotel to get some sleep. Tony, my sister and I stopped for a drink at the hotel restaurant, Michael Jordan’s Steakhouse. I had the El Train (recommended by the bartender since they no longer carried my first choice, Zombie Dust) which was a delicious IPA.

Not wanting to end the night early, Tony and I braved the rain and stopped at Dublin 4 Irish Pub and Cafe for a drink where I tried (and highly recommend) the Apex Predator Farmhouse Ale. The bartender overheard us discussing where to go next, and he suggested we hit up Mother Hubbard’s Sports Pub. He informed us that bars along W Hubbard Street were open till 2:00 a.m., while some even stay open till 4:00 a.m. Per the bartender’s advice, we took an Uber to Mother Hubbard’s and had a few drinks while Tony pulled up TouchTunes on his phone and proceeded to play Gloria for the bar to enjoy (Lets go Blues!). Down the street from Mother Hubbard’s was Howl at the Moon, showcasing live music and dueling pianos. The bar was packed with people dancing and singing along with the pianists. We ended our night there and jogged back in the rain to our hotel, a mere two hours earlier than the time we woke up to begin the journey to Chicago.

Starbucks Reserve Roastery

A somewhat hungover Monday morning wouldn’t be complete without a trip to the Starbucks Reserve Roastery, in which customers coast up four stories of escalators and stop off at their floor of choice to purchase their favorite coffee and breakfast items (even though there are a plethora of other Starbucks and independently owned coffee shops around the city that won’t leave you feeling claustrophobic). When we left, a line was forming outside that began to wrap around the building.

Monday was mainly spent shopping, which was ideal since the Windy City was taking full advantage of its nickname. A cold front had come in overnight bringing with it wind and some snow flurries. We strolled along the Magnificent Mile, stopping by stores that were two or more stories tall. At Bloomingdale’s, we stopped at Aster Hall on the 5th floor of the store which houses a unique food court. There are touch screens along the wall which are used to order the food you desire. There were many choices ranging from burgers, to sandwiches, to pizza, and even sushi. After changing my mind a million times, I chose to order chicken fried rice from Lost Lily’s. A receipt with my order number was printed out and I walked to find the Lost Lily’s area. Each restaurant in the food court had a screen which displayed order numbers that were in progress and order numbers that were ready to be picked up, making it easy for customers to find where their food was being made and when their meal be done. The portions were large, the fried rice was delicious, and I felt reinvigorated (and slightly less hungover).

The Signature Lounge was the next pit stop between our shopping excursion. The Signature Lounge is located on the 96th floor of the John Hancock building. We were able to snag one entire side of the bar and ordered drinks while taking in an immense view of the city. My aunt mentioned that one of the best views of Chicago can be found in the women’s restroom (sorry boys) and I did not pass up the opportunity to go in and take a few pictures. One Bloody Mary and a final glimpse of the city later and we were back to shopping, which gave me the opportunity to warm up as the temperature continued to drop outside. Before long, it was time to head back to the hotel to gather our belongings and begin the trip back to STL.

Rarely does a trip end without a bit of drama. About thirty minutes in to the train ride, some noises at the front of the train were heard and the emergency brakes were engaged. Over the intercom, the conductor notified the passengers that the train had hit a car and an investigation would have to be carried out before the trip could commence. After some time we were informed that there were no casualties and the car had been abandoned on the tracks. The mood on the train shifted and passengers became amicable, discussing what could have led to the accident. For the next few hours we were stuck on the train while the investigation was taking place and the engine was being assessed (I utilized the time by catching up on some true crime podcasts, of course).

Five hours of being stranded on the tracks and a few podcast episodes later, we were offered some good news: we would be making it to STL. However, the train had to go back to Chicago first. By the time our train was pulled back to Chicago, it was 1:00 a.m. If the trip had gone accordingly, we would have already been back in our beds passed out from the amount of walking we had done and drinks we had consumed. The five hour train ride had turned in to a thirteen hour debacle, finally arriving in STL around 8:45 a.m. Tuesday morning. While the train ride ended up being uncomfortable and unpredictable, it was interesting experiencing something that many people have only witnessed in movies or television. Thankfully no one was hurt, passengers were able to make it to their destinations, and I left Chicago and the train ride with a fascinating story to tell.

Until the next adventure ✈️