June 16-20, 2025

I wanted to check out some new things for clients. I thought I would take a quick trip to Chicago on Amtrak. I have traveled by train in Europe and thought this would be similar. It was not. Scheduled to leave at 9:57 pm, we left our departure station at 10:30 pm. Never riding on Amtrak before I had several misconceptions. When booking, I selected first class. I wanted a sleeping car for the trip. It was especially important since the journey was at night. Arriving on the train we were shown to our sleeping car. Claustrophobic beware! The sleeping car was the width of a twin bed consisting of two chairs facing each other. The chairs had to be arranged into a twin bed. The second bed (my bed) was much smaller and was lowered from the ceiling. Upon arrival I asked directions to the bar for a night cap. I was quickly disappointed when told that it was closed. So off to bed it is. This proved to be a gymnastic feat in its self. One can not raise your head or your knees while lying in the upper bed.

To add anxiety to the fire there were safety ropes to catch you if you should roll off the bunk. So once in bed and somewhat comfortable we were off on our journey to Chicago. What a short night. It was as rough as could be. Trains whistled every 15 minutes or so. Did I mention that you couldn’t even roll over in the bed?! By morning, I was determined to not let this set the tone for the trip. I gladly went to find a cup of coffee. The Dining Car was located a car or two from the Sleeping car. It was nothing more than a few booths where you were served pre-made pastries. (Insert sigh here.) After “breakfast” we returned to our car and having the beds removed relaxed in our chairs as we watched Missouri pass by us. We arrived in Chicago at 1:44 pm at Union Station. I loved the feel and ambiance of the station.

It was like walking back in time. According to Google maps, we were within 5 blocks of the hotel. This is what I had planned for. We didn’t have to Uber or Taxi everywhere. After an hour of walking and the app kept turning us in circles we gave in and called an Uber. It was in fact 5 blocks from the station in the opposite direction!

The Crowne Plaza would be our home for the next couple of nights. The room was spacious and nice with a balcony overlooking the busy streets of Chicago. We took a quick break and refresher. Then we made our way to the Riverwalk. There, we boarded the First Lady, Chicago’s architecture river cruise. We learned about Chicago’s various architectural styles and the people who built and designed the city. Beware photo overload.

After our cruise tour we made our way to O’Callahan’s Pub and Grill. One of my travel friends owns the bar and we just had to meet up with him for a drink. O’Callahan’s is a must visit if in the River North District of Chicago. The wait staff and food were the best.

On to day two – June 18

Today’s agenda is laid back and easy. We began with a walking food tour of Chicago. I purchased all my tour tickets through Viator and I would love to share the site with you. The tour was called “Bite into Chicago.” It consisted of trying a Chicago style dog. We also had a Chicago Italian Beef Sandwich. Of course, we finished with a Chicago Style Deep Dish Pizza.

Even though this was a food tour our leader pointed out interesting facts along the way. Plus an added bonus we got to ride the “L” which I learned stands for Elevated Train.

Quincy Stop is another Chicago landmark, being maintained as close to the original as can be. And we even experienced a Chicago downpour all in the same day. Quick jot back to hotel, change and then off to see the Second City. This was on my husband’s bucket list and we were able to add that check. I was surprised at the improv and comedy that was portrayed there.

On to the next day June 19 the third day

My husband has a cousin that lives outside of Chicago and she and her husband met us for breakfast. It’s always fun meeting up with cousins

Then to Wrigley Field and my all time favorite BASEBALL!

Even if we lost (8-7) it was a great game and we loved it. We ventured away from the field. We found a bar called the Dugout and visited it. We met several fellow Cubs fans there and shared our table with them.

Next on our agenda is a sunset cruise on the River and Lake Michigan

Last day in Chicago June 20 -day 4

We slept in and then packed up. Our train wasn’t scheduled until 1:52 pm. This allowed us to check out. They maintained our luggage till we returned. 10 am and we are off on a walking tour with Colin. We entered many buildings. some used as offices. Some used as a bank. Some were actually department stores. The architecture of the buildings are gorgeous and well maintained through the years.

The outsides were gorgeous. There’s no words for the insides, gold and tile and marble were everywhere. It was definitely from a time when Chicago was in its youth and growing fast.

You can see the essence of Frank Lloyd Wright in one of the interiors. His influence is evident in the designs.

And what would be a trip to Chicago and not see the famous Bean?  A quick trip to millennium Park where we get to see the Cloud Gate a.k.a. the Bean.

We squeezed in as much sightseeing as we could, and then it was back to the hotel to pick up our luggage and then move onto the union station to catch our train

I will have to say the return trip wasn’t as bad. We left in the middle of the day. This allowed us to see the scenery as we made our way south. We also wander around the train some. Noise-canceling headphones helped greatly. They improved sleep on the return trip. Not to mention, the bar was also open.

Contact me if you would like to travel!