City Girl: Chicago Summer and Meeting Pirates
- Stan Hecht
- Aug 26
- 10 min read
Updated: Aug 26
I am sitting on an Amtrack train at 8:57 on a Sunday morning in July. The train was scheduled to leave at 8:58am and arrived early at the station. I was just getting up to go to the bathroom when everyone in the small Alton station jumped up and headed out to the platform. I turned to see the train racing into the station. The train station was not staffed that morning, so there was no warning that the train was even arriving. Had anyone been a minute late, they would have missed this train.
We grabbed our suitcases, headed out, hopped on and within one minute the train began moving.
Because the conductors’ separate passengers according to destination, we were in the last car which was crowded and dark. I headed upstairs to find better seats. Leaving our luggage, we relaxed into giant, comfortable seats with a lovely window and relaxed.
Not for long. The club car began announcing blue plate specials, the conductors came by for tickets and other directions were announced. Rachel, who was in the club car kept us laughing with her funny announcements all the way to Springfield, Illinois.
I also found a train car with lounge seats and giant windows.
Settling in for the four- and half-hour train ride, I pulled out my book, got comfortable and began to read. There might have been a few minutes’ delay for freight trains, however, other than that the train ride went as smoothly as you would want. I will say-the bathrooms were disgusting. Enough to make me think twice.
Arriving in Chicago Union Station, we looked for our Uber and headed to the Congress Plaza Hotel across from Grant’s Park on Michigan Avenue. https://www.congressplazahotel.com/ This is a lovely hotel, the rooms are newly renovated and it’s in an excellent location. We came early in the week as Lollapalooza was coming in for the weekend. Added bonus: the air conditioning worked like a dream!
Dropping our suitcases, we headed out via the El to the Wicker Park Fest.
I love street fairs, and we had fun exploring the many vendors and shops along the way.
There was even a shared pina colada!
Wicker Street also boasts a few really cool re-sale and vintage shops. In one, I found a funky gold jacket from Cache, a now-defunct clothing store from the ‘70’s and 80’s. It was cute even with denim shorts. Wicker Park Fest - Wicker Park & Bucktown Chamber of Commerce.
We had plans to meet at North Beach, calling for an Uber, not knowing that half the streets were closed. We ended up calling the Uber driver who was parked exactly where he said he would be, although as visitors we had no idea. It all worked out, and we ended up on time, enjoying the late afternoon and evening at Castaways Beach Club with magnificent views of both the lake and the city.
And I enjoyed visiting Stan’s sister Dena who is always fun to be with!
We walked along North Beach as far as we could before hopping an Uber back to our hotel. The day had been hot and humid; however, it had cooled off enough for us to enjoy being outside. Castaways Beach Club | 1603 North Lake Shore Drive, Chicago IL | Beachfront Bar & Grill
Monday morning, we decided to have a real vacation morning sleeping in and finding a place for breakfast by you guessed it, googling: “breakfast near me.” We walked through the Columbia College Chicago campus admiring the artwork and murals finding ourselves at Eleven City Diner.
We felt as if we had discovered the most amazing diner ever! All on our own. (We found out later that most people in Chicago know about the place and love it as much as we did.)
Walking in, the hostess said we had a few minutes and suddenly I hear, “Are you here to buy the place from me or just wandering around?”
I twirled around to find a man who looked very familiar, but I couldn’t place him. He took one look at me and I think he realized the same thing. It turns out we both went to Mizzou, but at different times. Now, Brad Rubin was running, quite successfully Eleven City Diner and had been for twenty years. He was a blast, making us laugh and visiting our table which made the brunch even more fun.
The food at Eleven City Diner was exactly what we had in mind. Eggs, omelets, French Toast (omg, challah French Toast!)
Mmmmm and Eli’s Cheesecake. We had not heard of Eli’s Cheesecake, but apparently, it’s a famous Chicago thing. And well worth it! Perfect addition to any meal.
Eleven City Diner is an old school diner and deli and they more than live up to this! They serve lunch and dinner, drinks, and fountain treats. I was ready to have every meal here. Thank you, Brad, for an amazing diner and deli and for your hospitality.
We stayed at Eleven City Diner for over two hours enjoying the leisurely brunch, chatting, and relaxing. It was after all, vacation. We stayed so long that I eventually made a reservation for a class at Lifetime the following Monday!
If you know me, you know that even though I might be ON vacation, I’m all about the go-go-go. It was very hot and humid, and we knew we had a long, fun day planned for the next day with family and friends.
Completely out of my nature, I said, “What are your views about enjoying the hotel, the air conditioning and having a lazy afternoon of reading or watching a movie?”
For the next two hours, we relaxed in the very cold hotel room, reading, sewing and very happy. My thrifted shorts had lost a button and luckily the hotel supplied a little sewing kit.
We met up with the rest of our party at The Harold Washington Library Center which was two blocks from our hotel. What a beautiful building and a sanctuary for anyone who needs it.
I happened upon this while looking around. Way to go Harold Washington Library!
We loved the Children’s section which took over most of the second floor and offered many sections of exploration, including a hanging Lego board, a puppet theatre, soft building blocks and a miniature food truck complete with costumes. Oh, and it was stocked with books!
The Winter Garden, which is an atrium on the top floor offers comfortable couches and seats. A perfect place to rest, study, read and enjoy the sunshine.
Heading to dinner, we walked a few blocks, looking for a park (not finding it) and made it to Lou Malnati’s. We had been here last year, although at a different location. We had a reservation, and they stuck to that time-the place was packed. Lou Malnati’s is famous for deep dish pizza. While I love pizza, I no longer can tolerate mozzarella cheese, and most places will substitute another cheese if they have it. I found out last year that Lou Malnati’s doesn’t do that. They don’t deviate from their menu. They have gluten free crust and other items including appetizers, sandwiches, and salads. I had meatballs and a little salad which was delicious. https://www.loumalnatis.com/
We had talked about karaoke down the street or finding music after dinner, however, we turned in early. It was so nice to be in the cool, quiet hotel room.
The next morning, we had breakfast at LaSalle Café Luna which was light and perfect to start our day.
Walking along Michigan Avenue, we passed the Art Institute of Chicago (tribute to my Uncle Steve who earned one of his degrees here years ago) and a big part of my first trip to Chicago when I was 16.
We headed to Cindy’s Rooftop for a view of the city. https://www.chicagoathletichotel.com/restaurants/cindys/
It was early and not crowded yet, so we had the opportunity to scope out city views and take photos.
Looking out we saw The Bean and decided to head there.
It had been years since I was at The Bean and I have to say, it still is amazing.
The Bean is a great place for people watching, too.
Trying to get the selfie….
We had a great time taking pictures from all angles.
I loved seeing how others took their photos and how much fun they were having. https://www.choosechicago.com/articles/tours-and-attractions/the-bean-chicago/
Along Michigan Avenue we stopped into Stan’s Donuts to check it out. We had a Stan with us which made us all laugh.
I wish they would have had a t-shirt-that would have made my day!
Stop in and ogle the sweet treats. For some reason I missed the Nutella Café. How is that possible?
Before heading to the Chicago Riverwalk, we had another photo opportunity and Chicago stepped up.
Along the Riverwalk, we stopped at Island Party Hut for lunch and fun.
There were games for everyone of all ages and a beautiful view.
We enjoyed lunch and adult beverages and then set out to walk to Navy Pier. It wasn’t a far walk and it was fun to walk along the river.
We stopped at Harry Carey’s giant baseball glove and met a family from Denmark who were touring the city. They asked if it was always this hot.
Ducking inside so part of our group could build a bear, I found a little empowering women’s shop that made me smile and say YES! https://navypier.org/location/confidence-apparel/
Stopping in a candy shop, and I got caught with my hand in the candy jar.
Along our way we decided to sit and rest at The World Famous Billy Goat Tavern and Grill. Sharing a drink, it was nice to sit outside under fans and rest. https://www.billygoattavern.com/
Suddenly, Delaney, who is six said, “There’s a pirate! Mommy, daddy, I see a pirate!”
It’s not often that anyone says that here in the United States. I stood up to where Delaney was pointing and sure enough, there was a pirate!
Delaney and I grabbed hands, and ran out to The Windy where we called out to the pirate.
“Ahoy, matey!”
The pirate heard us and came out to see who was asking.
He smiled when he saw us and I asked, “Say something in pirate.”
He obliged, “Shiver me timbers!”
We smiled and laughed and returned to our table reporting back that we had indeed met a pirate. (as an aside he was a pretty good-looking pirate, but that is another blog) https://www.lakeshoresail.com/
By this time, it was time to head to Offshore for our dinner reservation. https://www.offshorerooftop.com/
We had stumbled upon this rooftop gem last year. Offshore offers beautiful views of the lake and has both outdoor and indoor seating.
When we stepped off the elevator, there was a young man dressed in white holding a bunch of flowers. I looked at him and said, “good luck!” thinking that he was apologizing for something or waiting for a first date. Turns out, he was waiting for a special young lady to propose! Which we watched from
inside. He had two friends recording and got down on one knee. As soon as she said, “Yes!” they had big smiles. Then, the hostess brought out what looked like family members, and they proceeded to celebrate with champagne on the deck. Such a fun thing to experience. Wishing you the best of everything and a long, happy life together.
We decided to take a water taxi back to the hotel and walked almost back to the hotel to reach the taxi.
Once on it, we were gifted with beautiful scenes of the city from the water.
Such a unique view from the water, especially at sunset.
Reaching our hotel, we said goodnight, reserved an Uber for the next morning and packed up.
Our last morning, we had breakfast at LaSalle Café Luna and packed our leftovers with a $5 bill for the man we saw sleeping by our hotel handing the bag off to the helpful bellman. (we also saw a rodent run across the street, but I cannot even talk about that)
We waited for our Uber that never came, so the bellman asked if we wanted a ride with their driver, Steve. It cost a little more, however, we had a train to catch. Steve had great stories, and we felt as if we had lucked out with this ride. I messaged the uber driver more than once asking where they were and didn’t here back until we were almost to Union Station.
We grabbed lunch items and got in line for the train. Amtrak had us get into train cars based on our destination. We found seats and traveled through rain and storms, sunshine, and many stops.
Settling in with my book I wondered how quickly we would get back to Alton. And yes, a VERY good book!
I also knew I would have to make a reservation for classes the following Wednesday at Lifetime. I had backup; however, I was hoping I would have internet as we passed through various stops.
Success!
Once more I found the Amtrak train dirty, unkempt and gross. The trays had not been cleaned; there were food crumbs everywhere and the bathrooms were to the point of disgusting beyond words. One bathroom door was taped up with red duct tape and didn’t lock. I came back to my seat and said, “I can’t do this again!” There is simply NO excuse for how nasty the bathrooms were or the fact that the train was not properly cleaned. I’ve been on trains all over the northeast and never found this. Amtrak clean up your trains!
In addition, we had a delay that Amtrak knew about and emailed us:
Delay Notification: As of 10:58 AM CT, Train 319 is operating approximately 35 minutes late. We apologize for the inconvenience and thank you for your patience. For customers waiting to board this train, please be aware that departure estimates are subject to change. If conditions allow, a train delayed past its scheduled departure time may leave earlier than the updated estimate. To avoid missing your train, please stay near the boarding area and monitor for announcements or updates.
In addition, we had another delay ON the tracks lasting at least 30 minutes, possibly longer because of freight trains.
However, on this train ride, we traveled through Springfield seeing the state house which is beautiful.
Though we cannot see that from a plane, I thought that if we had flown, we would have been home in the swimming pool three hours earlier.
I was glad to finally get back to the Alton Station and enjoy the afternoon and evening.
I love Chicago. And thoroughly enjoy the summer trips to the big city. This year I especially loved that I was able to relax and not go-go-go. That I was able to have a relaxing afternoon, too. To be completely honest…meeting a pirate was pretty cool, too.
Special thanks to Stan Hecht for all the adventures, Kristen and Erik Cole and their girls, Marie Rincon and Dena Hirschberg and Lou Nork. Love being part of this summer trip!
Expect Good. Defy Gravity! Sparkle On. Shiver me timbers! This City Girl loves Chicago!
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