November 27-30, 2025
The day before Thanksgiving is the second-busiest travel day of the year in the US, only being surpassed a few days later on Sunday. However, flying on Thanksgiving itself is far more manageable, and generally cheaper.
As such, I had an early Southwest flight from Sacramento to Chicago, direct with no layovers – only about 4 hours. Yes, it left at 6:30, but I normally work at 4 am on Thursdays, so it was easy to get up and make the hour or so drive.
The great thing? There was hardly ANY traffic!
I left my car in the overnight lot, something I’ve done several times before. I didn’t have to check any bags, and while security was longer than normal it still didn’t take too long. While I waited in the terminal I thought about what this weekend would hold.
I was flying to Chicago because my sister-in-law’s family is from there, and we were invited for Thanksgiving. They, on the other hand, will come to California for Christmas. Any excuse to see my nephew who just turned a year old! Of course, on one of the days I planned to see the city itself, as I had never been, and I would fly out in the evening on Saturday to miss the Sunday traffic. (It did not end up panning out that way, but we will get to that later…)
My flight there was smooth. I snagged a window seat and I had some good views of Lake Tahoe, Salt Lake City, the Mississippi River, and eventually downtown Chicago, interspersed with a few naps and some snacks.
Getting out of the plane and airport was fairly easy – I had flown to Midway (MDW), the smaller airport towards the southern metro area of Chicago, and was picked up by my sister-in-law’s brother Joel.
Waiting outside for him, it was COLD. I had been warned that the temperatures would be pretty low, so I had come prepared with heavy clothing in my backpack, and I got it on pretty quick! It was in the 20s and 30s most of the time I was there, with the high over my few days being only 35 degrees!
Anyway, the drive was smooth, it just took about an hour as they live all the way up in Deer Park, a far northwest suburb. It was a nice house, with a ton of backyard – over an acre on the whole property.
Eventually my family (my parents, brother, sister-in-law, and nephew) showed up – they had driven up from Nashville early that morning.
The rest of that day was mostly just hanging out with family (like celebrating Peter’s first birthday, which was the previous week) and a bit of planning for when we’d go down to the city and explore. It also snowed a bit at one point, a small foreshadowing of what the weekend would hold.
Friday was when the Thanksgiving celebration was properly held, as the in-laws’ family from Fort Wayne, Indiana came up. We ate some delicious food, played a few games, and overall had a really nice time. Part of me wanted to explore that morning, but I decided against it and just slept in. We also decided that Saturday would be our city exploration day, and that I would go with my dad and Justin.
Since there would be a pretty substantial amount of snowfall that day, we had decided that we would take the train into the city. Once we were done with the day, I would take the train straight to O’Hare International Airport (ORD) where I would be flying out of, while my dad and Justin would just head back to Deer Park.
My family was staying at a hotel in Schaumburg, about 30 minutes south, and on Saturday they came to the house around 7:45 before my dad, Justin, and I were dropped off at Barrington Station, about 10 minutes away. We bought tickets at a kiosk outside, and had a smooth ride into the city, taking a little over an hour.
Getting to Ogilvie Transportation Center just before 9:30, we headed into the cold to begin our walk. Originally we had planned on doing Willis Tower for the observation deck, but due to the weather conditions there was really no point. Visibility would be practically zero, and it would have been a waste of money.
As such, our first goal was getting to the Bean, but this would mean we’d have to walk about a mile straight east. So we set off through the snow, hoping to find somewhere along the way like a coffee shop we could stay at for a little while.
As we walked, one thing I really appreciated about Chicago was the architecture. It was a combination of new and old, modern high-rises and skyscrapers mixed with art deco buildings and historic landmarks.
I was definitely reminded of New York City from the 2 times I’ve been there, though there were much fewer people on the streets due to the snow, which made the morning walk a little calmer to me. We also passed by the famous “L” train, though we did not ride it at any point.
Something else which reminded us of NYC was the CBS News station, which they were filming right inside! We saw the weather reporter as she was giving the forecast, and the main newscaster was sitting at a booth inside, though we did not see her give any live news as we wanted to keep moving after a few minutes.
After about 30 minutes total of walking from the station, we emerged into a more open area and crossed the street into Millennium Park. There are quite a few things here, as it extends for several blocks east and south, but we would only stay in one area due to the snow.
First off, we saw the Chicago Christmas Tree, full of bright lights and decorations! We then passed by an open park area in front of a monument, which was covered in snow and surrounded by autumn trees. Later on as we left the area, we saw a kid making snow angels there!
However, what we were really here for was just to the right past some stairs – the Cloud Gate, unofficially known as the Bean. This is one of the most iconic landmarks of Chicago, having a shiny reflective surface with a small archway you can walk through. It was actually much bigger than I realized – it caught me off guard!
We also walked towards the Jay Pritzker Pavilion as the crazy architecture caught our eye – it had a fence surrounding it but we could see that it was an amphitheater! Makes sense that it was closed with so much snow.
As we started to leave Millennium Park, we wanted to get a picture in front of the Christmas tree. Luckily, a nice couple offered to take some for us, and after Justin returned the favor to them, we headed out.
The next thing on our list was Giordano’s, a famous Chicago restaurant chain known for their pizza – we wanted deep-dish while we were here. But it was only around 10:15 and they were not open yet, so in the meantime I found a Cinnabon where Justin and I got warm drinks and some cinnamon rolls. There was just enough seating for us to snag some spots, and we stayed here for a good 35 minutes as we watched the weather continue to worsen, especially the wind. They really call it the Windy City for a good reason!
Luckily, Giordano’s was only about a block away, so after fighting the wind a bit to get there, we made it inside. It wasn’t quite open until 11, but they were letting people in to wait in the lobby area. Once they opened, we got in line and were led to our seats.
It didn’t take us long to decide what we wanted. We would all be sharing a 12 inch deep dish called “Meat & More Meat” (pepperoni, sausage, salami, and bacon). Now, it was not the cheapest thing in the world – $40 for a pizza – but it was the top thing on my list and it was not a bad decision. The only downside (besides the price) is that it takes about 45 minutes to cook, but we were well aware of that before we visited, and it gave us more time out of the snow.
When we finally got our pizza, we saw why it took so long to bake. I knew that the sauce would be on top, but all the other toppings were as well. Not only that, but basically the entire pizza is stuffed. It’s almost like the opposite of a stuffed crust pizza! The waitress put a slice on each of our plates to start, and the cheese pulls were legendary – she did it like a pro!
The pizza itself was absolutely delicious – probably one of the best I’ve ever had. It was a completely unique style compared to anything I’ve had before, and there was just so much cheese – my favorite! We actually had to eat it with a fork and a knife because it was so gooey and thick. It was hard to finish – we didn’t think we’d be able to but we managed to polish it off. I wasn’t hungry the rest of the day though!
After this we headed off back into the flurry, which had picked up significantly, and we headed up towards the Magnificent Mile, the main commercial district. The buildings continued to loom over us, and eventually we got to the Chicago River again, as it goes around the Loop.
Rather than going to the Magnificent Mile immediately, we actually pivoted and decided to head towards Navy Pier. As the name implies, this was originally built by the Navy, but is now a series of attractions, restaurants, and more – though the important thing was that the whole building was enclosed.
We tried to seek refuge where we could along the way. Firstly, there was an area underneath the main street of Magnificent Mile where we could start walking towards the pier, which gave us a couple of blocks out of the snow. After a few more blocks of snow in our faces, we found a Target to temporarily rest at – one of the strangest ones I’ve ever been to!
We eventually found our way to Navy Pier, and I have to say the decorations surrounding it were very nice to see in the snow. But it was also nice to be inside for a while!
Navy Pier is a super long complex, and we were planning to go to the end to see what we could of Lake Michigan. But we were okay with taking our time, as it meant we would have time to warm up and dry off!
Eventually we walked the furthest we could go, to the locked doors of the Aon Grand Ballroom. Justin and I decided to go outside here, to go to the end of the pier. There was so much snow outside, and the wind was getting crazy this far out.
At the end of the pier it was so bad there were huge sections of ground with literally no snow, because it was all blowing away. The wind was probably 40 miles an hour! The visibility on the lake was pretty minimal, though the waves had whitecaps and looked like they were from the ocean.
We found our way back inside (my dad let me in, while Justin went around), and we found a place to charge our phones a bit since the cold had been draining my battery. While waiting, my dad decided to check how much we’d walked so far, and we had gone over 5 miles! I think we ended up with around 8 or 9 total by the end of the day.
From here we headed back to the Magnificent Mile. My dad and I were pretty tired (I think all the pizza caught up to us), but Justin was eager to go further. We walked about 5 blocks north, and I do have to say the decorations and buildings were quite nice. It was very festive, with bright signs, advertisements, and lit-up trees. Justin also tried to convince me to go to a Harry Potter store, but I really wasn’t interested in buying anything, so we moved on pretty quickly after going inside.
At the end of our 5 blocks, we briefly saw the Chicago Water Tower, a castle-like limestone tower which actually survived the Great Chicago Fire in 1871, having been built two years prior. But at this point my dad and I were pretty tired, so we began walking back.
We eventually got back to the river, and decided to go inside Trump Tower to seek refuge because Justin and I thought it would be funny. There were actually some nice places to sit inside and rest a bit, though we had to brush a lot of snow off!
After a few minutes of rest, it was time for us to start heading back. Because I would be going straight to O’Hare, I would leave from a different station than Justin and my dad. After crossing the river we didn’t have to go terribly far though, it just felt like a long distance since we were tired, cold, and our shoes were wet from the slush. We finally made it to where my station (Washington) was, right near the Christkindlmarket – we did not go inside here but it was at least a pretty sight.
Once I made it inside, I was going to buy a ticket (my previous all-day ticket from Barrington did not apply on this line), but I realized I could just tap my credit card to get through. The ride from there was smooth, about 50 minutes to the airport on the blue line.
There were a couple notable things though. The first was a guy going around asking if anyone wanted gum, which seemed super sketchy. There was also a guy who looked like he was homeless that was just sleeping all the way to the end of the line, but I did not feel like disturbing him. On the other hand, I noticed a couple of girls speaking in Japanese who were clearly tourists – they got off on the stop before the airport where a lot of hotels must be. Overall in Chicago I definitely noticed a lot of visitors from outside the US, more than I would have expected.
After getting to the airport around 5 (and seeing a surprising amount of beggars in the station), it was a fairly easy process to get in, with nobody in the security line. I was there pretty early since my flight was delayed multiple times, so when I got to my gate I decided to just take a nap. After about an hour of sleep I saw my flight was delayed once again, all the way until 11 pm. As such I decided to find other rebooking options, and there was one supposedly boarding very soon, so I chose it and immediately headed to a different terminal where it would be.
Unfortunately, it was not that easy. The flight coming in was delayed, and even after it eventually arrived and people deplaned, they had to check a mechanical issue with the landing headlights. When they couldn’t fix it, they tried to get a part from the hangar, but that didn’t fix it either, so around 10 pm our flight was finally canceled.
I had to call to rebook, and the soonest option would be 2 layovers, not getting back until 6 pm. Luckily, I was able to get 2 meal vouchers worth $15 each, as well as a hotel. Weather cancellations don’t generally lead to a free hotel from the airline (in this case United), but mechanical issues do lead to vouchers, so in a sense I got lucky. I was barely able to catch the shuttle, being the last person inside before it was full, and it was about a 25 minute ride from there to Best Western Schaumburg.
The funny part was that I was only about 5 minutes from the hotel where my family was staying, though I would be leaving earlier than they would since they’d be driving back to Tennessee the next morning. After I checked in with my voucher code, I was put on the list for the 6am airport shuttle, and got my room key. The room itself was definitely not bad, two beds I could choose from with one being right next to the heater. I was not awake long before piling into bed, as I would have to leave in less than 7 hours.
Unfortunately, I ended up getting less sleep than that, waking up around 5 am, but I just decided to stay awake. I headed down around 5:50 and waited until about 6:10 for the shuttle. Traffic ended up being terrible, and we didn’t get to O’Hare until around 7:10. Security also took me nearly 45 minutes to get through. This was exactly why I wanted to avoid traveling on the busiest day of the year.
On the bright side, I was able to switch flights to one that was actually direct to Sacramento! I would be in a middle seat, but who cares? One flight would be much more manageable than 3 different ones. (I’m pretty sure those ones got delayed anyway.)
I finally got to my gate, and decided to use one of my meal vouchers to have a small breakfast. The plane eventually arrived, and everyone deplaned. While boarding was delayed a bit, it finally started around 9:25. While in line I noticed that they were working on deicing the plane, which was to be expected considering the still-freezing temperatures. I actually made it on, and though I was in the middle it was all the way up in row 8. Good tradeoff.
Good thing I had those vouchers.
It took us quite a while to actually leave – about another hour – but it wasn’t much of a problem for me since I just started watching Return of the King. The flight itself was pretty smooth, only a few bumps. I would’ve liked to look outside more, but the woman to my right was sleeping, so I didn’t want to open her window. After I finished the first movie, I decided to also watch Planes, Trains and Automobiles since it’s a classic Thanksgiving movie. By the time it ended I had just about landed, with only about 10 minutes to go.
Once we finally made it I was super happy, as I had had one heck of a journey getting back. At least I made it back by 12:45 pm rather than 6 pm, which would have happened if I’d had the 2 layovers. To use up my last meal voucher, I decided to grab a grilled cheese sandwich to-go, and ate it on my way back to the parking lot.
Finally making it to the car, I was ecstatic. I only had a bit of traffic on the way home, and was back by 2:15.
It was unfortunate that I happened to visit Chicago during the snowiest November day in its history, but I still had a good time regardless. I got to see family, eat good food, and had a few hours to experience the city, even if not in optimal conditions.
My journey there and back was full of ups and downs. I had traveled by planes, trains, and automobiles, but when I got home I felt like Samwise Gamgee at the end of the Lord of the Rings trilogy – “Well, I’m back.”