CHICAGO: Three and a Half Days in the Windy City

People keep asking me which city on my trip was my favorite and I’ve gotta say, I think it’s Chicago. The Windy City had the whole package for me: things to do, really tasty food, and I stayed in a fancy hotel. I’m ready to go back if only to eat more deep dish!

The Southwest Chief

I wrote a separate post for my other big rides, but the Southwest Chief was fairly uneventful. It was most like the California Zephyr ride being that it was 34.5 hours and took me across the country from Flagstaff, AZ to Chicago; the scenery was a lot better on the Zephyr though. The Chief has a sightseer car but you’re only going to see deserts, plains, and cornfields for the most part. I spent several hours working in front of the large windows, working on my current manuscript and chatting with an older couple who’d also bought a rail pass.

It was a full train the whole time with TONS of Boy Scout troops that kept boarding. My seatmate for most of the trip was a troop leader who told me they’d been out in the woods for 12 days and that he’d chased off a bear the night before and showed me a picture. Mr. Troop Leader also informed me he was an oral surgeon and has his pilot’s license; he showed me God knows how many pictures of his family up in a private plane and their travels. To be rich enough to hop in your private plane with the fam and go above cloud level to look at the stars. Y’ALL. I teach at a ritzy private school, but that’s next level.

Anyway, besides the Most Interesting Boy Scout Troop Leader in the World, the only other out-of-the-ordinary happening was the singing lounge attendant whose voice was what you’d get if you combined Kermit the Frog and Fozzy Bear. This man sang over the loudspeaker every couple of hours to announce the closing/opening of the cafe car. But you know what? You can tell he loves his job.

*PRO TIP: There’s a long stop in Albuquerque! Go through the Amtrak station, across the street and you’ll see Silver Street Market where you can get food.

What I Did in Chicago

I was so ready for a shower and good food when I arrived in Chicago late on a Tuesday afternoon! I met up with a friend from high school I haven’t seen in 17 years, we had Cuban food and caught up on life.

On Wednesday, I took the L to Skydeck Chicago in the Willis Tower; it’s definitely worth a visit. Before you even head up to the Skydeck there are neat interactive exhibits that teach you about Chicago architecture and culture. Then you take an elevator to the 103rd floor and you’re surrounded by floor-to-ceiling glass windows that offer 360-degree views of Chicago in all directions. They say on clear days you can see up to four different states.

The whole experience ends with The Ledge: a glass box that protrudes from the side of the building, and the floor is only made from three 1.5” pieces of glass…but can supposedly hold up to 10,000 pounds. Also, they’re SUPER strict with how long you can hang out on the Ledge; they set a timer that beeps at 60 seconds for 1-2 people and 120 seconds for 3-4 people/families.

Since I had a longer stretch of time in The Windy City, I decided to take it easier and chill for the day with one more excursion: seeing Buckingham Fountain in Grant Park. Little did I know the entire park would be off-limits because of stupid Lollapalooza.

After spending the rest of the afternoon relaxing at the hotel, I met up with an agent-sibling (one of my agent’s other clients) for deep dish pizza at Pizzeria Uno.

Thursday was jam-packed. In the morning, I took a Shoreline Architecture Cruise, one of Chicago’s top attractions. It took us on all three branches of the Chicago River and past a lot of famous buildings. I’m happy to report that Dave Matthews Band nor any other musicians dumped poop on my boat.

After the cruise, I went to the American Writers Museum–as a writer, how could I not? It’s a small place, but there was SO MUCH information that it was a bit overwhelming. The museum was incredibly interactive, and I love that there was such a focus on immigrant stories being part of the American experience.

Following my trip to the museum, I had a late lunch at Navy Pier before running home to hop on an agent-sibling Zoom call that night.

Since my train didn’t leave until Friday evening, I made the most of the day by going to Millennium Park to see the Cloud Gate a.k.a The Bean. I was jonesing for more deep dish so I got a mini pizza and salad for lunch from Giordano’s and ate it in the park. It was only meh; I think Pizzeria Uno spoiled me. After that, I spent the rest of the afternoon working on my manuscript in the hotel lobby before heading to Union Station to hop on the Lakeshore Limited to New York City.

Where I Stayed: Hotel Blake

Ahhh, this place was magical. Its location was in the heart of everything and perfect. Nearly every time I arrived back at the hotel, a bellman opened the door for me. The room was exquisite, and from my window, I had a prime view of the Willis Tower (where the Skydeck is located). I would absolutely recommend it and if/when I return to Chicago I plan to stay there again.

Notable Eats

• Osaka Sushi & Fresh Fruit Smoothies: My God, this smoothie (and the tuna avocado roll)! I was on a quest for ice cream but stumbled across this place. After the first sip of my strawberry-mango smoothie made with their fresh lemon syrup, it was no surprise why so many people were dropping in just to grab smoothies. I braved the Lollapalooza plague-spreaders and stopped back by for a pineapple-mango smoothie on my last day.
• Pizzeria Uno – House Salad, Shrimp & Crab Dip, and a Small Pepperoni Deep Dish: Even between the two of us we couldn’t eat it all but we made a dent. Pizzeria Uno is the birthplace of Chicago deep dish, invented in 1943. It was super cool eating at a historic landmark. It was so delicious I wanted to eat it a couple more times before leaving Chi-town.

• AD&B (America’s Dog & Burger) – Louisville Dog with Fries: I really wanted a hot dog here in Chicago but I just couldn’t bring myself to get the traditional Chicago dog with pickles, relish, and all that jazz…ick. Since I was at Navy Pier and the Louisville hot dog was the “Navy Pier favorite,” I had to try it! It’s a deep-fried hot dog with smoked cheddar sauce, chopped maple bourbon bacon, and onion strings on a pretzel bun. Utterly delicious…but I think I’ve shave a few months off my life.

• Garrett Popcorn – Garrett Mix: I’d never even heard of Garrett Popcorn until I stepped foot in Chicago, and then I saw Garrett Popcorn shop stores and people carrying the striped bags everywhere. On my last day, I decided to pop into a store and get some for my train ride. I got the Garrett Mix, a blend of yellow cheddar and caramel corn, and it was really good.

Overall Thoughts

Chicago was great! One thing I love is that the CTA system is so easy to use. You’ve got your colored lines, different entrances, everything is well-labeled and tells you exactly where to go.

One thing I didn’t love is all the noise. There were constant sirens and firetrucks; it’s like the big fire put the fear of God into Chicagoans and it’s still there however many years later. But it’s a big city so what can you do?

Songs Added to the Playlist

Just one song to add: “Call It What You Want” by Foster the People. I heard it during one of my breakfasts and got the very welcome feeling of being back in control; much needed after Los Angeles. Check out the full playlist here:

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When it comes to pizza, are you #TeamDeepDish or #TeamNYStyle?
If you’re from Chicago, what other deep dish places should I try on my next visit?