Mother-Daughter Trip

Chicago Landmarks, Bridgerton Ball, SpeakEasy Tour, and Great Food

Chicago, Illinois

April 27-April 29

Dear Friends,

I hope the week is treating you well. In my last post, we traveled to St. Louis, and now we are going to Chicago by train. I will say this train trip was a lot more reliable than the train between Jefferson City and St. Louis! I do need to mention here that a lot of this trip will be a Catholic pilgrimage, but sections of this trip are dedicated to time with family and to good food. It is actually several trips in one. This time in Chicago is a mother-daughter trip. During this part of the trip, we will visit Chicago landmarks, go on a private SpeakEasy Tour, dance at the Bridgerton Ball, and enjoy marvelous food.

On the morning of April 27, the morning I ended the last letter with, we woke at 4:15 AM. This was so we could still have time to have some coffee before we made our way to the train station at 5:15 AM. Our train was due to leave for Chicago at 6:40 AM, but we needed time to find an Uber and the website for Amtrak recommended that passengers arrive 1 hour ahead of time.

At 5:15, Roxanne, who has the Uber app on her phone, found an Uber eight minutes away and so we headed outside to wait. It was still dark and cold out at this time, however, there were lights and heat lamps on under the hotel’s awning. We waited ten minutes and the Uber did not arrive. Roxanne, looking at her Uber app, said the driver had not moved and was still eight minutes away. We talked about walking to the train station because it was only an eleven-minute walk, however, at the reception desk last evening they had highly discouraged us walking at this time of morning since it was still dark. Finally, twenty minutes later the Uber arrived and we made it to the St. Louis Amtrak Station.

As the Uber drove us, I was glad we had waited and not walked. Indeed, the area was very sketchy and dark. When we arrived, we found that there had been no reason for us to leave so early. We were just told to have a seat and wait. We did not even have to show our tickets until we were actually boarding. We did not need to check our suitcases either because they did not have a luggage car. They told us we needed to keep our suitcases with us. That was perfectly fine with us and because we were traveling Business class our steward on the train stored our suitcases behind one of the seats.

The train ride took less than 6 hours and we arrived at the Union Station in Chicago at 12:30. I have only been to the Union Station in Chicago once before and I will say I was impressed. Possibly because the first time I came here, back in 2019, I had been nervous about the crime stories I had heard about Chicago and train/bus stations in general across the country. On that occasion, not only was I impressed by Union Station but the area around the station as well, which was very nice. So, this time I saw the station through the eyes of someone who had already been there and yes, it is very much a train station, but the building is beautiful, cleaner, and larger than the train station in St. Louis.

Coming up into the central part of the station we easily found the sign above one of the exits for 8^th Street, the street we needed. Then we walked eleven minutes to the Kimpton Gray Hotel on Monroe Street, where we would be staying over the next couple of days. We passed several businesses, shops, and restaurants along the way, but what we found most impressive about this area of Chicago were the skyscrapers, each one individual in its’ design, yet coordinating perfectly with the other buildings around it. However, at this time I did not have the time or energy to focus on this cityscape because I was walking with my large suitcase along and carrying my travel backpack on my back.

The Kimpton Gray is a beautifully designed modern hotel right in the Loop area around the Financial District. The hotel’s reception is on the second floor next to the lobby area where they have complimentary Happy Hour each evening between 5:00 PM and 6:00 PM. Our room was on the 9^th floor with a large tiled walk-in shower and a huge globe hanging light over the shared nightstand. It is this large white globe hanging low between the beds that draws the attention when you walk in. We both really liked this touch of modernity in the room.

By this time, we were both very hungry and decided to walk to Gino’s East for Chicago Style Deep Dish Pizza. Roxanne had read about the restaurant and they were rated one of the top pizzerias in Chicago to serve this delicious local food. -And no wonder! The pizza was amazing! Different than any pizza I had had before. The crust was crunchy at the bottom and then topped with homemade sauce, sausage, onions, green pepper, and lots of cheese. I was thinking before the pizza arrived that the crust, especially at the center, would be soggy like deep dish pizzas are sometimes, but it was crunchy instead. We had to use forks and knives to cut the crust, but the taste and texture, with the toppings, went perfectly together.

If you do decide to go to this restaurant, Gino’s East is very laid back, not fancy at all. They do have a full bar and you should prepare to wait a while for your pizza. They make each one fresh. We waited an hour for our food. However, the wait was worth it. They do not take reservations, but at 2:30 PM, when we arrived, it was not busy at all.

On the way to and from Gino’s East, we marveled at the buildings. Roxanne particularly liked one very modern-looking all-black building. The structure was a rectangle and smooth, like some sort of metal, all black with black windows. It sat between other skyscrapers and buildings, all with a more classic look to them, making the black rectangle stand out as a perfect contrast to the older, more ornate styles around it. Near here was one of the many iron bridges that carried the city train above ground. The bridge’s sides were like latticework in a rust color. This industrial look again was a perfect contrast to the surrounding buildings. Everywhere you looked there were these contrasts, but the whole scene mixed perfectly together as though a Master artist had created it.

We ate late in the day because in the evening we were going on a Private SpeakEasy Tour. This tour is something we both were very excited about and we had booked it about six weeks ago through Viator. It was very expensive, but because it was something we both really wanted to do, we did not mind. As promised by this tour company we were picked up at precisely 7:00 PM from our hotel. The guide met us in the hotel lobby. I was not expecting this and I was waiting outside the main entrance to the hotel. Roxanne texted me to say the guide had texted her and was in the lobby, which I thought that was very nice.

He was a very nice young man, very eager to share his knowledge of hidden places in Chicago, Al Capon, the 1920s and 1930s, and his favorite SpeakEasy establishments, some historical, some modern. He led the way to a luxury black suburban with a driver who opened doors for us and helped us into the vehicle. They had water bottles for us and small snacks.

The first place they took us to was the Green Door Tavern, the oldest tavern in Chicago. It dated back to the Great Chicago Fire, being built over the top of an older tavern that had been burned down. Down in the lowest part of the tavern was a private door that led to a SpeakEasy that was established during the Prohibition. Unfortunately, we were not allowed to go in because of a private event going on, but they did allow us to peek in through the door. Upstairs we had our first drink. I opted for sparkling water, saving for later the Old-Fashioned I planned to enjoy later in the evening. I asked the tour guide where the best place for an Old-Fashioned would be and he told me it would be at a place called the “Untitled Supper Club”. They had the best traditional Old Fashioned and several whiskies to choose from.

Two stops later we were at the “Untitled Supper Club”. As we walked in, I saw at least three rooms with people gathered, but our tour guide led us to one in particular. Inside was dim with green lighting and a lady was performing acrobats on a large hoop dangling from the ceiling. We sat down in velvet-covered seats and I ordered an Old-Fashioned with a sweeter whisky off the whiskey list and our tour guide started telling us about the life of Al Capone, who had played a huge part in Chicago Mafia history. I will say this SpeakEasy was by far my favorite place that evening, and I believe it was Roxanne’s as well.

Next, we went to the Palmer House, which is an opulent hotel owned now by Hilton. Along the way, we drove through the Financial District of Chicago and I saw the buildings that I had seen on our walk lit up for the night. There was a building with the name TRUMP across it. Then we drove along the river and our tour guide regaled a ghost story for us. He told us back in 1915, near where we were driving along the Chicago River, one of the worst ferry accidents in US history happened. It was on a day that was supposed to be a wonderful day designed to give the factory workers in the city a holiday. It was to be a picnic on an island in the middle of the river and they had to take the ferry, Eastland, across to it. Lots of families with children went as well as single men and women. Most were young adults and families that were immigrants who had come to America for a new life.

There were two thousand five hundred and seventy-two people on board the ferry, which was her max capacity. For some reason, within fifteen minutes of departing, the passengers started to shift all to one side causing the ferry to capsize not far from the riverbank. Eight hundred and forty-four people were lost. This is not all. The river at that time was nicknamed, “Bubbly Creek”, because it was so thick with pollution, and so these poor souls not only drowned, but they drowned in muck. The tour guide told us then that there had been many sightings of corpses and people calling out from the river when a passerby would walk by. The sight of these bodies would be so real that the witnesses would call the authorities. When the authorities arrived, the person or corpse would be gone.

We only had one more SpeakEasy to go to. This was Palmer Hotel, a very elegant and wealthy hotel dating from 1871. Here in the “Lobby Bar”, they served traditional cocktails from the 1920s and 1930s. This hotel had been one of Al Capone’s main places to hang out. There is a room at the top of the staircase overlooking the Lobby Bar that leads into a room where he discussed a lot of his dealings. This extravagant hotel had been built to impress and draw the elite after the Great Chicago Fire. The paintings and sculpting on the ceiling and walls reminded me of some of the palaces I had seen in Austria, as though the room had been decorated by a master cake designer. Again, like at the St. Louis Union Station, it was easy to imagine the ladies and gentlemen of the rich in the 1920s socializing here with Al Capone smoking a cigar and discussing his plans with the Mafia.

We sat in plush chairs and ordered the oldest American cocktail known as the “Sazerac”. The classic cocktail dates from 1871 and is made with Bulleit rye, Montenegro amaro, absinthe, demerara syrup, and lemon peel.  The cocktail reminded me of an Old-Fashioned, except with a hint of licorice and they served it straight up in a martini glass rather than in a tumbler on the rocks. We enjoyed it but all too soon it was time to head back to our hotel.

I would highly recommend this tour to anyone who is a history buff, interested in classic drinks, or who is interested in Al Capone. Both the tour guide and the driver were very courteous and friendly. It was a little pricey, but it was also well done. On this tour, you have to pay for your own drinks as well which I think should have been included in the tour price. However, I would definitely go again. To book your own tour, check it out here!

The next day was Thursday, April 28 and we woke to the sky being overcast. This was a disappointment because we wanted blue skies for our pictures.  Today we were visiting some of the iconic Chicago landmarks before attending the Bridgerton Ball in the evening.

Before setting off to sightsee we enjoyed breakfast at the Roanoke Restaurant, a four-minute walk from the hotel, and then we walked another twenty minutes to the Sky Ledge inside Willis Tower. This is a very popular tourist destination and you must make reservations online before arriving. We had reservations for eleven o’clock and as we walked the clouds broke up some and the sun tried to come out.

We found the building and going in we saw a food court full of unique takeaway shops. One was called “Brown Bag Seafood” which I thought looked especially interesting because they served the food in takeaway brown paper bags reminding me of how in years past fish shops in England would serve the takeaway fish and chips wrapped in newspaper. Of course, they cannot do that anymore, the ink of the newspaper not being considered safe on the food. I made a mental note to perhaps eat at
“Brown Bag Seafood” the next time I was in Chicago.

From the food court, we took the escalator and then the elevator to the floor where the entrance to the Sky Ledge was. Here we showed our pre-bought tickets and walked through a winding hallway full of places to snap selfies. One-stop was a huge Chicago Style Deep Dish Pizza that you could sit on with mirrors behind to take a picture. Another spot was a Chicago Style Hotdog that you could sit on to take another photo, and there were several other Chicago-themed selfie photo stops.  

Then we came to the line for the elevator that would take us to the Sky Ledge. This part of the experience I was not prepared for. Once on the elevator, you travel up one hundred and three stories and as you go, up pictures show on the elevator wall of different heights of buildings around the world. Each time you see a picture of a building, an announcement gives the height of the building and you keep going up. It was when we passed the top of the Empire State Building that I felt my stomach lurch a bit. I will say the elevator is enclosed. It would have been a lot more frightening had it been only windows like some elevators are.

At the top, there were two glass ledges, enclosed by glass. The ceilings and floors on these two ledges were also glass so that when you stepped out onto the ledge it was like you were in mid-air. Surprisingly after my stomach tipped on the way up in the elevator, I did not feel any fear on the ledge. It was kind of like looking out a plane window only it was all open. Below the buildings, cars and trains looked tiny as though I was looking for a toy model of Chicago. It was not blue skies as we had hoped, but not as overcast looking as it had been that morning either.

We only had two minutes on the ledge to take pictures so we quickly posed and snapped the pics. Then we were off so the next people in line could take their pictures. The attendant at the ledge has a timer, so everyone gets exactly two minutes. Coming down the elevator was easy and then we headed to Chicago’s famous “The Bean”.

Now, when my son, Ryan, and my daughter, Roxanne had told me about “The Bean”, I thought it sounded very silly because this sculpture sits right in the middle of Chicago’s Millennium Park and people come from all over the world so they can take a picture with “The Bean.” However, we made our way there from the Sky Ledge, about a twenty-five-minute walk. As we walked it was very cold and windy. It is no joke that Chicago is nicknamed the “Windy City”! The wind comes off the Michigan Lake and the Chicago River funneling with force through the streets between the tall buildings. If you come to Chicago during cold or even cooler weather you may want to bring something to cover your head- especially your forehead because the wind is very direct and intense.

Keeping my head down to break the wind, I finally looked up and there it was in front of us, “The Bean”! I laughed when I saw it. It was huge, in the shape of a pinto bean, only it was all mirrored in silver. I discovered quickly why it is such a popular tourist place. In the curved lines of the bean are mirrored the spectacular cityscape; every few steps gives you a different version of the scenes around you, including yourself. So, every picture you take has a different look and curve. Now I am not one to take selfies but both Roxanne and I spent a good half an hour having fun taking pictures. I am glad I went to see “The Bean”. It is free to everyone and being outside it is a fairly safe place to visit during these times with COVID.

By this time, it was about two o’clock in the afternoon and we were very hungry. We waited to have lunch because we were going to the Bridgerton Ball in the evening and the venue was not serving food. So, I made reservations for us at 9:00 PM in the hotel’s restaurant, BOLEO. The ball was going to be over at 8:00 PM but it would be a long stretch between lunchtime and 9:00 PM if we had eaten closer to noon.  So, we began looking for a restaurant and found one called, “Rosebud”. The building did not look like much but on the billboard above the door was written, “Italian Food Fine Dining”.

We went in, not expecting much with the way the outside looked, but the hostess led us down into the basement which was small and very elegant. Surrounding the intimate dining room, Italian statues beckoned from ornate alcoves, while white tablecloths on tables spoke of a more elegant time. At our table, a very distinguished waiter, with a crisp white cloth draped over his arm, took our order. Even at two o’clock in the afternoon, almost every table was filled. We ordered off of their extensive menu, both of us choosing the cavatelli from the waiter’s recommendation. I have never had cavatelli before. It was the best Italian pasta I have ever had. It was homemade and tasted like what I had over the years envisioned what an Italian mom or grandma would make for her family. The portion of food was very large but I managed to eat all the pasta.

We arrived back at our hotel just in time to get ready for the Bridgerton Ball.  I had arranged for a private transfer to the venue and they were collecting us at the hotel at 5:30 PM. They were picking us up from the venue to bring us back to the hotel as well. The doors opened at 6:00 PM with the ball starting at 6:30 PM.

For those of you who don’t know what the Bridgerton Ball is, it is based on the Netflix series, Bridgerton, a period romance about the “Ton”, the aristocracy, during Regency-era England. The story is at times narrated by Miss Whistledown, who writes a weekly society column, in which she always begins with, “Dear Reader”. She then tells the “Reader” the secrets of the Ton, including the actual names of those she is gossiping about. Miss Whistledown’s identity, herself, is kept secret from almost everyone and no one is safe from her sharp eye and whit.

The main family in the series is the Bridgerton family, and the Dowager Viscountess Violet Bridgerton is a widow with several children. Each of the series focuses on one of these children who has become of age and who is being introduced into London Society. Like other mothers in her social class, the Viscountess Bridgerton is intent on introducing this new adult to the most respectable and wealthy of the Ton, in the hopes of procuring a much-sought-after marriage for them. During this process they are presented to Queen Charlotte, attend balls and fashionable social events, and, of course, they find romance. This romance must dodge Miss Whistledown’s tell-all column in order to avoid society gossip and disgrace. Of course, each season’s hero or heroine finds their true love, a love that must be proven worthy to each other, London Society and the Queen. Scandals come forth and love matches are made all against the backdrop of a glimmering London Season.

Roxanne and I were both very excited to attend this ball, and to enter, even for a short time, this dream world of romance and happy endings. 

For my costume, I wore a reproduction of an early 1900’s dress with a square neck and puffed short sleeves. It was very plain and black. Unfortunately, I had waited too long to order a dress from Amazon and this plain black one was the only one available in my size on Amazon before the ball. I guess size “Large” is sold out quickly. So black it was, but then, as I told Roxanne, I am a mother, grandmother, and widow, so the color black was fine. To make up for the plain black dress I wore long white satin gloves past my elbows. I wore my hair up with a coronet and a large silver and rhinestone necklace encased with pearls that matched this simple crown. For shoes, I wore silver dancing slippers.

Roxanne wore a beautiful shimmering gray-blue silk gown that fell straight to the floor in the Regency style. She could have been the main heroine, Daphne, out of the first series herself. Like me, she wore the long white silk gloves that had been worn by all the ladies during the Regency period.

The event was held at the XS Tennis and Education Foundation and it was not as crowded as I thought it might be. As we entered the venue we walked beneath an archway of wisteria and there we had a chance to have a portrait made of ourselves that looked just like a Regency Painting. However, the work was done with modern technology and we could capture the image on our cell phones to have for later.

Here they had beautifully crafted cocktails with names that came from the Bridgerton series. Roxanne had a “Diamond” cocktail which was pink and served over ice in a champagne glass with a fresh flower on top. Soon after we arrived, the Queen was announced and she walked regally to her red velvet throne, followed by her lady in waiting, everyone curtsying as she passed by. We each had a chance to present ourselves to her and to curtesy, as she haughtily looked on, sometimes even with a raised eyebrow. However, every so often, if she was pleased, the corners of her mouth would tilt up in the tiniest of smiles. I did not fare so well, my knees not being what they used to be, and so I actually received the raised eyebrow. On the other hand, Roxanne’s curtsy impressed the Queen, and right after leaving the Queen’s presence, she received a nice card on thick paper, trimmed in gold, from an elegantly dressed footman. The card announced she was one of the debutantes being considered to be this Season’s “Diamond”. In other words, the Queen’s “chosen one” who would most likely make a grand marriage.

After these presentations, we were given the opportunity to dance the Quadrille in small groups to impress the Queen before we were invited into the ballroom itself. Here we were shown a couple of more early 19th-century ballroom dances and then with great care and courtesy the staff, dressed in royal livery, asked us to move back from the dance floor. That is when two professional dancers came out and performed a beautiful dance that captured the romantic stories from the series. The lady who danced the heroine’s part was dressed in a beautiful blue gown and with every step and expression added to the story of romantic love. The gentleman played his part perfectly and with grace as well. It was a beautiful performance combining ballet and expressive dance in an art form that surpassed anything I had expected. Following this performance, we were all encouraged to dance on the dance floor as well, and in true Bridgerton style, the music was a combination of the tempo popular during the Regency Era, using traditional instruments, yet the tunes themselves were recognizable as modern-day songs that we hear every day on the radio. That is what I like about the series, Bridgerton, although it took a while to get used to it, being the history buff that I am. Everything about the series is a merging of history, different cultures, music, dances, and evolving social questions. Yes, the time period is Regency Era, but you can see modern glimpses in every episode. This merging is very tastefully, purposely, yet gently done so the storyline seems to flow magically. I realized as I was dancing at the ball, that Bridgerton is not historical fiction but rather an expression of Art. I think that is why this series is so popular across the world.

Our coach, a black luxury suburban, was waiting for us when we stepped back out into the real world. Gone was the dazzling ballroom and we were once again on the highway headed back to our hotel. Still dressed in our costumes we went up to dinner at BOLEO, located on the hotel’s top floor where they served tapas and drinks. I cannot say the food at this restaurant was great. It was okay, but we were glad not to have to go out so late at night.

The next day was our last day in Chicago. We slept in and had a late breakfast at the Marq Restaurant, about a three-minute walk from the hotel. From here we took an Uber to the shopping district, not far from “The Bean”, so Roxanne could purchase some souvenirs for Hailie and Clayton. We also made a decided detour to Pandora for our own souvenirs. I purchased a bracelet to add charms too and also two charms, one with the cityscape of Chicago on it and one with a crown with the word, “Queen” written across it in memory of the Bridgerton Ball and the lovely time I had with my daughter. I will add more charms to this bracelet as the trip carries on. Roxanne chose two delicate rings that fit together and when they are joined, they look like a crown. She too bought this as a memory of her evening at the Bridgerton Ball.

It was then nearly 2:30 PM and I had to make my way to COVID of Chicago. I had made an appointment with them a few weeks ago in order to get a rapid PCR test for travel. I had to have this COVID test so I could continue traveling. I was leaving for my next destination that very night and Roxanne would be headed back home tomorrow morning. I will let you know what destination this is, and the next step of the trip, in my next letter to you. Happy Travels!

Until next week- Jody