I recently returned from a weekend visit to Chicago where I spent some time with my brother and our mother. We celebrated our mother’s birthday with a few days full of activity, including a satisfying Chicago Bears victory over the Los Angeles Rams at Soldier Field.

Bookings

This was a short domestic trip and everything was relatively straightforward to book. The major concern was getting everyone to the right place at times that worked for each person while providing our mother with the best experience possible.

Flights

The most notable thing about our flight bookings was that I was able to successfully use James’s 15% Delta SkyMiles cardmember discount before canceling his co-branded American Express card. Other than that, these itineraries are a result of plugging in our travel dates and booking the most convenient options.

• James
  • 54,400 Delta SkyMiles + 11.20USD per person
    • SEA-ORD on DL J
    • ORD-SEA on DL J
• Nicholas
  • 454.47USD (United Airlines TravelBank) per person
    • LAS-ORD on UA J
  • 23,500 American Airlines AAdvantage miles + 5.60USD per person
    • ORD-LAS on AA J

Hotels

The most difficult thing to book for this trip was our rooms at the Waldorf Astoria Chicago. That being said, I closely monitored the property’s availability in the months leading up to our visit and grabbed rooms as they popped into inventory. During our stay, my mother and I were both lucky enough to get upgraded to junior suites even though we were staying longer than James was.

• Constance
  • One room for three nights at the Waldorf Astoria Chicago for 95,000 Hilton Honors points per night (two nights) and one Hilton Honors Free Night Certificate (one night)
• James
  • One room for two nights at the Waldorf Astoria Chicago for one Hilton Honors Free Night Certificate per night
  • One room for one night at the Hilton Chicago O’Hare Airport for 60,000 Hilton Honors points per night
• Nicholas
  • One room for one night at the Hyatt Regency Chicago for one Category 1-4 Free Night Certificate per night
  • One room for three nights at the Waldorf Astoria Chicago for 95,000 Hilton Honors points per night

Activities

I knew that I wanted to make our time at the Bears game special and, while most seats at Soldier Field afford an excellent view of the action, I decided to splurge on a location that would stick with us for the rest of our lives. Luckily, there were three face-value tickets available on the 50-yard line in the United Club, which features enhanced seating and additional amenities. I grabbed them immediately and they didn’t disappoint.

• Three tickets with priority boarding for the Chicago Architecture Center River Cruise Aboard Chicago’s First Lady and Chicago Architecture Center admission for 77.28USD per ticket, inclusive of fees
• Three tickets for Chicago Bears vs Los Angeles Rams at Soldier Field in United Club Section 209, Row 19, Seats 12-14 for 778.44USD per ticket, inclusive of fees

September 26, 2024

Angela dropped me off at the airport for my afternoon flight. I didn’t anticipate eating on my flight, so I chose to dine at the Centurion Lounge before walking to my gate. I was happy to get to spend the day with Angela and Fitz before departing, but it meant I arrived in Chicago, after a relatively pleasant flight, close to midnight.

When we landed in Chicago and after parking at the gate, we were asked to return to our seats so that the plane could be pushed back one foot. Apparently, some type of sensor on the jet bridge would not allow it to extend to attach to the boarding door because of the positioning of the plane. Between getting the tug to push the plane and getting the ground staff back to operate the jet bridge, this delayed my disembarkation by thirty minutes.

While I intended to take the CTA Blue Line into the city, the jet bridge issue meant that I missed both the 2345 and 0015 trains. Feeling tired, I decided to Uber to my hotel so I could get some rest.

Check-in at the Hyatt Regency Chicago was quite friendly, as one would expect in the Midwest. The staff recognized my Globalist status and proactively offered me late checkout and some free water. My room was spacious and comfortable with a nice bathroom and very comfortable bed. I was very impressed by what is, essentially, a business hotel.

September 27

The breakfast buffet at the Hyatt Regency Chicago is included for Globalist members and is a pretty standard setup with scrambled eggs, various meats, pastries, and an omelet station. The scrambled eggs left a lot to be desired, but the omelet prepared for me by a friendly chef rescued the meal. The pastries were very good and the locally sourced doughnuts were delicious.

After breakfast, I spent an hour on the phone with a client before stopping in the Club Lounge to procure some Kind bars and a cappuccino for my journey to Northwest Indiana. The lounge, on my very brief visit, seemed very nice. In the future, I can definitely see myself spending some time there reading, writing, or working. On balance, I recommend the Hyatt Regency Chicago for Hyatt loyalists looking for a cheap option in Chicago on points.

I walked to Millennium Station and purchased a ticket for the South Shore Line to Miller. The setup is much better than it used to be, with intuitive ticket kiosks that accept contactless payment located adjacent to the tracks.

My train ride from Chicago lasted a bit under an hour and James and our mother picked me up when I arrived. We took a ride down memory lane, literally, driving past all the old spots on the way to our childhood home. When I walked in the door, I was greeted by Stella, the new family dog. She very excitedly welcomed me with plenty of licks.

James and I spent a few minutes looking through some old stuff from our childhood. Before long, we were posing in our old letterman jackets. They fit just like they did in high school.

With some time to kill, James and I headed to Classic Bodyworks Gym, the first commercial gym either of us joined and a place that holds a special place in our hearts. When we walked up to the counter, we were lucky enough to find Al, the owner and operator of the gym, waiting to greet us. We chatted for a little bit before starting our workout.

It was just like old times, with James and I moving some serious weight in a place that feels like it is meant for the serious lifter. We set up on the deadlift platform and James smashed a single at 405 pounds. I was feeling pumped after witnessing it and pounded out a set of eight at 455 pounds sans straps or shoes.

Before we left, we procured some Classic Bodyworks t-shirts to rep the gym with pride. I got the chance to wear it a few days later.

We returned to the house, made sure our mother had all of her things, and then our mother’s friend, Susan, drove us to Miller Station for our journey into the city. I bought tickets at a kiosk inside the newly renovated Miller Station and the train arrived at the station less than five minutes after we walked onto the platform.

When we arrived at Millennium Station, we walked along the pedway to the CTA Red Line at Roosevelt and took that north towards our hotel. Alighting at the Chicago stop, we walked the rest of the way to the Waldorf Astoria Chicago.

When we arrived, I checked my mother and myself in while James did the same for his reservation. Oddly, James and my rooms weren’t ready at the time of check-in even though we arrived almost two hours after the official check-in time. Luckily, our mother’s room was available so we headed up there to relax for a bit.

The junior suites at the Waldorf Astoria Chicago are quite nice with amazing bathrooms, an excellent sitting area, and a very comfortable (though a bit soft for my tastes) bed.

Our mother loved the hotel and seemed positively giddy enjoying a cup of coffee on the couch in front of the fireplace.

Shortly after we arrived, a flower arrangement was delivered to brighten our mother’s room up. The colors were quite apropos for the weekend.

We sat and chatted for a bit while James’s friends who live in Chicago made their way to the property so we could enjoy dinner together. We opted for Lou Malnati’s as our mother had never had it before. On the way out of the hotel, James and I were able to retrieve keys for our rooms.

Because we decided to eat a little early, we easily procured a table after walking the few blocks to the restaurant. We ordered an absurd amount of food, in all honesty. James chose to have a house salad and personal vegetarian pizza, while I opted for a Caesar salad and a medium Chicago classic that our mother ate a single slice of. We also split an order of deliciously fresh-tasting bruschetta.

After everyone was well and truly stuffed, we returned to our mother’s room to watch the second half of the Virginia Tech vs Miami football game before everyone headed to their own room for the night.

September 28

We met at the hotel restaurant for breakfast. There’s something on the menu for everybody and every dish I tried during our stay was delicious. I ordered French toast, a pair of poached eggs, and a flat white. James chose avocado toast, roasted potatoes, and drip coffee. Our mother opted for eggs Benedict and drip coffee. Our server, coincidentally named James, was very friendly and helpful, going so far as to replace our mother’s saucer when she spilled a bit of coffee.

After our meal, James ordered us a Lyft to take us to our architecture tour. I chose to purchase priority boarding tickets to ensure we would have our choice of seats and that our mother wouldn’t feel pressured on her way onto the boat.

I really enjoyed the architecture tour. Our guide was clear, informative, knowledgeable, and funny. The information he presented was delivered with just the right mixture of levity and gravitas. I recommend the tour to anyone interested in learning a bit more about Chicago’s storied history.

After disembarking, we walked up the stairs to street level, stopped at a Starbucks for a pick-me-up, and then enjoyed the Chicago Architecture Center. While small, the exhibits are very high quality and I am glad we made the time to stop and enjoy them. My favorite part was the scale model of the city set in front of a movie screen that shares a history of development in Chicago.

James called a Lyft and we headed back to the hotel so that our mother could nap in advance of the evening’s activities. While she laid down, James and I walked to the River North location of Ramen-San where we enjoyed a tasty and filling meal.

James ordered the edamame hummus, a spicy tofu mantou bun, and the tantan-san ramen. I opted for the karaage chicken nuggets and 10 hour tonkotsu ramen accompanied by a deliciously fruity Thank Yuzu mocktail. I enjoyed the the karaage more than the ramen, but it was still a tasty bowl of soup. I think I’m just spoiled by the extremely high quality ramen I’ve had this year, both at home and abroad.

We walked back to the hotel. On the way, James was accosted by an unhoused person and was chased around me twice before the individual lost interest. All’s well that ends well, though, and we made it back to our lodgings without any other issues.

When we arrived, I ordered our mother room service so she could have an easy and peaceful dinner. She enjoyed the French onion soup and Casear salad and was happy to sit and eat them at her room’s desk.

We watched the Texas A&M University vs Arkansas game until it was time to go see Kings of Leon in concert. Paulette picked us up and we drove to Huntington Bank Pavilion at Northerly Island. Paulette splurged and secured us VIP seats, which were quite comfortable.

While I’m not a huge Kings of Leon fan, the concert had good lighting and sound design and a tight production with minimal interruption. They waited until the last song of the encore to play Use Somebody, by far their most popular song.

After the concert, Paulette dropped us off at the hotel and we all headed to bed for some much needed rest.

September 29

For breakfast, I joined James in having avocado toast while our mother tried the pancakes with a lemon and blueberry confit. She thought they were tasty, if a little sweet. That may have been because of the additional syrup she poured on them, though.

We met in the lobby at 0945 and, after James checked out, we walked to a nearby bus stop to catch the 146 line. We decided to take the bus because it would get us much closer to the stadium, and lead to less walking, compared to the CTA Red Line. Sure enough, the bus dropped us off close to our entry gate.

After a short walk and a single set of stairs, we found ourselves at Gate 38 and then inside the United Club. The entry process was straightforward and the United Club’s amenities didn’t disappoint, with nicer bathrooms, sitting areas, plenty of TVs showing other games, and enhanced food options. We found our seats and got our mother settled in before James and I set off to get her a pretzel with melted cheese.

The seats were awesome with an incredible view. I liked that we were covered and our mother was protected from the rain, sun, and wind. The game was entertaining, with the defense playing very well and the offense doing enough to outscore an offensively talented opponent. More than anything, it was nice to spend the day watching the game with two people I love.

We exited the stadium and saw the extremely long line for ridiculously crowded buses. I nixed the idea of returning to the hotel on the line that we had rode inbound, thinking it would probably be better to get on the train as it should have been less crowded. We headed that direction but paused at a bus stop and took an alternate line (the 3) towards our hotel. We had to walk about a third of a mile after leaving the bus to reach our lodgings.

Our mother decided to take a nap while James and I went out for a pre-dinner snack. We chose to eat at Velvet Taco. I opted for brisket and chimichurri steak tacos while James chose cauliflower and paneer tacos. Both of my choices were absolutely delicious and, judging by the speed at which James devoured his selection, I’m assuming his were, too.

James and I went back to my room to watch the afternoon games and give our mother a little more time to rest. We went to her room at 1830 to see if she wanted to go grab some dinner. After she confirmed that she was hungry, James called a Lyft to take us to Butcher & The Burger.

We each created our own burger. James chose the vegan patty with umami seasoning, American cheese, and a whole wheat bun. Our mother ordered a sirloin steak burger with simple seasoning, American cheese, and a pretzel bun. I opted for a bison burger with simple seasoning, cheddar cheese, and a split top bun. We all shared a basket of cheese fries.

I thought my burger was absolutely delicious and highly recommend this restaurant. After dinner, I called an Uber to take us back to the hotel. We stopped in our mother’s room so James could grab his bags and say goodbye. Afterwards, I walked him to the nearby CTA station so we could chat for a little bit before he left for his airport hotel (as he had an extremely early flight the night morning).

On my walk back to the Waldorf Astoria, I stopped at Walgreens to buy some ice cream to enjoy as I wound down from a delightful day of football and family.

September 30

After the trip’s last breakfast, I helped our mother pack and called an Uber to take us to Millennium Station. After making arrangements for our mother to be picked up when she reached Miller, we entered the station, walked to the train, bought a ticket, boarded my mother for her journey home.

When the train left the station, I walked back to my hotel, stopping at Firecakes Donuts on the way. The doughnuts at Firecakes are wonderful, and I highly recommend anyone who finds themselves in Chicago grab a couple.

I spent a few hours working before checking out of the hotel. I still had a whole afternoon to burn before my late evening flight, so I decided to stop at Portillo’s for lunch. I specifically chose to eat at the location that Angela and I used to visit whenever I would come up to the city during breaks while we were in college. I couldn’t decide between having hot dogs or an Italian beef, so I had both.

After lunch, I sat by the Chicago River for a few hours before taking the CTA Blue Line to ORD. While there, I did some writing before hopping on my plane to head home. Angela picked me up and thus ended a short, but meaningful, trip.

I had a great time in Chicago for the weekend. I enjoyed spending time with my brother and mother and we made some memories that will last a lifetime. I couldn’t have asked for a better set of experiences.