Chicago, October 2022

I recently returned from a trip to Chicago where I went to a Thursday Night Football game at Soldier Field, spent an afternoon with family, and met up with some friends that I’ve known for a few years in an online-only capacity. Of a 28-person online group chat that I’m a part of, 14 people showed up. Given my other experiences with getting a group of adults to do anything, this was an outstanding result!


There’s nothing particularly exciting about the bookings for this trip, but I do want to share them and give my reasoning for booking things the way that I did.


  • Nicholas
    • 601.60USD per person (American Airlines gift cards)
      • LAS-ORD on AA J
    • 573.02USD per person (American Airlines gift cards)
      • ORD-LAS on AA J


I chose the hotels based on my activities I had planned for the nights I was in the city. For the first night, I’d be walking to Soldier Field and wanted to stay relatively close. This led me to stay at a property near McCormick Place. On the second night, I’d be having dinner with my friends and decided to stay where they’d all be staying so we could have pre-dinner drinks before heading to the restaurant.


I love going to NFL games but it certainly isn’t cheap to do so. I purchased tickets in the upper deck around the 45-yard line to get the best view of the action and was quite pleased with our vantage point.

  • 197.83USD per person for one person for a ticket to Washington Commanders vs. Chicago Bears at Soldier Field

Thursday, October 13, 2022

We woke up early and Angela drove me to the airport. I quickly cleared security and walked to my gate, arriving about ten minutes before boarding started. The flight from Las Vegas to Chicago was uneventful. I was pleasantly surprised by the quality of the fruit and granola plate that American Airlines provided as a breakfast option. The fruit was fresh and the granola and yogurt were both high quality. The coffee was a bit middling, but I don’t expect much from airlines in that capacity.

When I arrived in Chicago, I walked to the train and took the Blue Line to Clark/Lake where I transferred to the Green Line, taking that to Cermak-McCormick Place. From there, it was a half mile walk to my hotel. I arrived a bit before the official check-in time and, unfortunately, my room was not ready. I requested lounge access while I waited for a key and the staff member was happy enough to provide it for me.

I was fairly impressed by the size of the lounge and the relative quality of the snacks and drinks on offer. The space seemed perfect for someone looking to get some work done or to relax and read a book.

The lounge closed at 1500 (apparently they plan on expanding to regular hours at some point, but haven’t yet) and I decided to wait in the common area until my room was ready. I received a notification that my digital key was available to use at 1530 and was able access my room, bundle up a bit, and then head out for some dinner on the way to Soldier Field.

I ordered a steak burrito from La Cantina Grill and picked it up on my walk to the stadium before stopping at a park near the restaurant to eat. It was tasty and filling, exactly what I needed to prevent me from buying twenty-five dollars of hot dogs at the game.

After a brisk twenty-minute walk, I was at the stadium. After a few pictures outside, I was able to quickly enter because the crowds hadn’t arrived yet.

Once inside the stadium, I secured my commemorative towel and then explored the exhibits on the mezzanine level before continuing to my seat.

From my seat, I was able to take in the surrounds and enjoy the pre-game atmosphere. I took a bunch of pictures, watched the punters and kickers warm up, and enjoyed the cool evening on my own while I waited for the rest of the fans to start arriving.

About half hour before the game, my buddy showed up and we were able to enjoy the football-like substance produced on the field. While the Chicago Bears didn’t win, they did score a touchdown, we all got to sing our silly fight song, and the atmosphere was electric until the very last minute of the game. Unlike last year, where there was high expectations of Matt Nagy turning Justin Fields into a superstar NFL QB overnight, fans were just happy to take what exciting plays they could get this year. That certainly made the experience a whole lot more fun.

We parted ways after the game and I walked back to my hotel as part of a swarming mass, the typical state of egress from the stadium.

Friday, October 14

In the morning, I visited the lounge to eat some hard-boiled eggs and imbibe a fair bit of coffee before some friends arrived in the city. After a few hours, the three of us met up at Ann Sather for breakfast, where I ordered a pair of delicious cinnamon rolls. They’re just as good as they were fifteen years ago when Angela and I were still in college.

After breakfast, we returned to my hotel to chat for a few hours before the three of us walked back to the Red Line and headed north. I proceeded to lunch with my mother and Paulette while the other two headed to their hotel to check in. For lunch, I chose Sushi-San on a recommendation from a friend because their menu offered both raw and cooked items and I knew that my mother would be able to find something that would suit her palate.

We had a delightful lunch where my mother ordered the Vietnamese pork and Paulette and I both chose the deluxe ngiri set. The general ambiance was nice, the service was excellent, and the food was delicious. I was a little taken aback when an optional Restaurant Surcharge appeared on the bill, but I requested its removal and allocated that money towards the tip instead.

After lunch, we walked to Cheezcake Boutique for dessert. A small mall vendor, the sweet treats were surprisingly delicious.

We chatted for another hour before parting ways. It was nice to see my mother and Paulette for a few hours during my short visit.

I walked to the Waldorf Astoria to check in and, even though it was 1630, my room was not yet ready. I was a bit surprised, but decided to just settle down in the Peacock Lounge and hang out with a few buddies who had already secured their rooms. After chatting for a bit, I was able to collect my keys and drop my bag in my room. I really liked the fit and finish at the Waldorf Astoria Chicago and would recommend it to others staying on points. I’m not sure I’d consider paying the average room rates that they’re charging, though.

I met back up with my friends at the bar where I enjoyed The Impostor, by far the best tasting mocktail I’ve ever had.

An hour or so later, we made our way to LuxBar, a hip spot that was crowded and loud when we arrived, but quieted down over the course of our meal. I chose the Aussie BBQ Burger and it was one of the best cooked burger patties I’ve ever had. The creamy coleslaw that came with my burger was decent, but not exceptional, and the appetizers we ordered were tasty, but less special then I expected.

After dinner, we chilled in a suite that one of our group was upgraded to before parting ways and heading to bed.

Saturday, October 15

The day started with doughnuts courtesy of Firecakes Donuts. A group of us met in the lobby and, after a short walk, enjoyed a delicious variety of treats. Personally, I chose the apple-cinnamon and espresso-cream flavored doughnuts and they were delicious. This is likely my second favorite doughnut shop in the world after Sidebar Doughnuts in California.

Once back at the hotel, I enjoyed an absolutely delicious double cappuccino before packing up. Just look at this beautiful porcelain in which drinks are served in the Peacock lounge:

After returning to the hotel and packing up, those of us staying at the Waldorf made our way to Time Out Chicago to meet up with the rest of our group. Luckily, two people had arrived directly from the airport and secured us a table in the center that we used in its entirety.

Time Out was a great place for the meetup and I was able to enjoy a variety of light bites including a sushi plate, some delicious asada tacos, and guava kolaczki (from a Colombian-Polish fusion restaurant, which is not a thing I expected to see).

We spent the next four and a half hours talking about the travel hacking hobby and getting to know each other. The time passed quickly and, before I knew it, it was time to go. In my view, the meetup was a roaring success with half the group showing up to meet each other and put faces and voices to names.

I set off to O’Hare Airport with a half-dozen other people who were flying out that evening and, once we reached the airport, I said goodbye to the rest of the party and headed to the terminal from which American Airlines flies. With a paucity of lounge options, I found an empty gate to relax at until my flight departed. The journey home was pleasant, with reasonable service and tasty snacks.

Angela was at the airport to pick me up when I arrived in Las Vegas, and thus concluded my short trip. While I was only gone for two nights, it felt like a complete whirlwind and, most importantly, was quite a bit of fun.

One response to “Chicago, October 2022”

  1. Sorry I wasn’t able to meet up with you during your visit. Thought maybe you could bring the Bears a win, maybe next time. Love you

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