Our 2024 Chicago Trip - Day 1

We just got back from a trip to Chicago (I’m sure many of you followed along on Instagram) and it was truly THE BEST TRIP.  Our family loves a big city, y’all!  I feel like all of us just thrive in a big city.  We all pretty much just thrive on vacation period, I suppose.  Haha.  I’m always the most laid-back version of myself (shockingly) when I’m traveling, Brian is a highly experienced world-wide traveler, and apparently, both of our kids got the travel bug from Brian and me because they are seriously fantastic little travelers. 

This was my first visit to Chicago, and I thought going in that it was also my first visit to the state of Illinois, but, surprise, surprise, I found out after our trip that I went to Illinois when I was 12.  Apparently, we drove through there when we took a two-week long road trip in 1994, and I had no idea that we’d done that.  So going in, I thought I was checking off the state of Illinois from my 50 states bucket list for the first time, but… I’d already been there.  Lol.  The kids got to check off their seventh state visited on this trip, though!  They’ve now visited Georgia (we live here – haha), Alabama, Florida, South Carolina, North Carolina, New York, and Illinois. 

A few random observations about Chicago before I get started on the recap since this was my first time going (and I’m mostly comparing it to NYC since I’ve been there so many times)…

 

-       Chicago is SO MUCH MORE LAID BACK than New York City.

-       It’s pedestrian-friendly, but it’s not crowded at all.  The only places we encountered lots of people were at The Bean and waiting in line on the Sky Deck to take pictures on the glass walkouts.  Other than that, it was easy breezy.

-       The traffic isn’t bad at all (or at least it wasn’t when we were there).

-       Everyone is so friendly.

-       Cars do not try to run you over even when you are crossing the crosswalks at the appropriate times.

-       It’s not super smelly like New York City.  In NYC, your nose is constantly being assaulted by car exhaust, sewage smell, food carts frying onions, cigarette smoke, weed, etc. but it wasn’t like that in Chicago.  While we did smell weed quite a few times and we did smell sewage a couple of times, overall, the air was pretty fresh.

-       We never once had to make a reservation for a restaurant and we were able to get in at every single place that we chose to visit right away.  And we often ate at peak mealtimes.  The only exception was Lou Malnati’s… the first location we attempted to eat lunch at had a 1.5 hour wait, but the girl there told us to walk a few blocks over to the other location and we were able to get in immediately.

-       The Uber drivers are pretty chatty there.  One guy was actually a little TOO chatty and he didn’t shut up for the entire time we were in his car.  Haha.

-       The river running through the middle of the city is A VIBE.

 

All that said, we absolutely loved Chicago, and we would definitely go back!  I do have to say that I still like NYC better despite all of the negative things I just listed above.  Haha.  But I think that’s just because NYC is so iconic… especially if you go at Christmastime.

Okay, now for the recap…

Wednesday, October 9

Wednesday morning, we were up at 5:30 AM and out the door to head to Atlanta before the sun was up because we had an early flight.  We arrived at the airport with just enough time to grab breakfast before our flight boarded, and the kids were excited about the assortment of pastries at one of the little cafes in the ATL airport.  I opted for a blueberry lemon scone (I LOVE a scone, y’all!), Brian had a banana nut muffin, Jacob had a massive cinnamon roll, and Olivia opted for… an assortment of macarons.  Hahahaha.  Y’ALL.  When on vacation, right?!

We flew United Airlines this time since Chicago is a big hub for United (hello, Home Alone!!!!), and that was my first time flying with them as we use Delta, like, 99% of the time.  Our flight was on time, and it ended up being smooth and good, but when we first boarded the plane, the captain came on over the announcements and said that the toilets weren’t working.  WHAT?!  He said that maintenance was on board trying to get them up and running, but ultimately, they failed.  Thankfully, he said that they would work once we got above 15,000 feet, but then they would shut off again once we got below 15,000 feet on our descent into Chicago. 

If y’all don’t already know, being without a bathroom is one of the ultimate anxiety inducers for me, so I expected myself to go into a downward spiral, but thankfully, that didn’t happen.  Normally, if somebody says there’s no bathroom, I immediately have to go.  Haha.  So, I was very grateful to my mind and body for not freaking out.

Anyway, the whole flight went off without a hitch, and we managed to get there on time even though we left a little later due to the maintenance crew working on the bathrooms prior to takeoff.  The kids did great, too.  This was their second trip to fly so they’re old pros now!  They both played trivia the entire time we were in the air.  United has a trivia game that you can play against other passengers on the flight, so the two of them played against one other passenger the entire time, and it made the flight pass quickly for them. 

Unfortunately, United does not offer free Wi-fi (get with the times, United!!) and I wasn’t about to pay for it, so I ended up playing trivia with the kids and listening to music for a bit on my phone to pass the time.  I had intended to post Amazon deals and do some Christmas shopping since Amazon Big Deal Days was going on, but I ended up opting out since there was no free internet. 

Once we landed, we took an Uber to the hotel.  It was about a 30-minute ride, and I was shocked at how little traffic there is in Chicago!  I guess I expected it to be bumper to bumper like New York City with tons of honking and aggressive driving, but y’all, Chicago is so laid-back compared to NYC.  We had a super pleasant experience driving in, and our Uber driver was so nice, too.  He even chatted with us a bit.  The Uber drivers in NYC do not chat.  Haha.

We stayed at the Embassy Suites on North State Street, and we loved everything about it.  The location was great, the hotel was super nice, they had a free, hot breakfast with tons of options every morning, they had a happy hour with an open bar and free cocktails/snacks every evening, and our room was a suite, so Brian and I had a king sized bed in our own room + a small living room (with a pullout couch where the kids slept), a bar area with a small fridge, a sink, and a coffee maker, and a decent-sized bathroom.  It was soooo nice to have all that space compared to the shoeboxes we always have to stay in when we visit NYC.  There was also the loveliest Italian bistro connected to our hotel that we ate dinner at one night, and there was a Starbucks on the corner next door.  WINNING.

When we arrived, it was still very early so we knew our room wouldn’t be ready, but we had the nicest concierge who held all of our luggage so we could go explore.  And we ended up getting a text that our room was ready shortly after we left, so they were ahead of schedule with the check-in time for us.

After we dropped our bags, we were on a mission to find lunch, because although it was only 1 PM in Chicago, it was 2 PM back home, so we were way past lunchtime.  We’d been told by several people that we had to eat at Portillo’s while we were there since it’s one of those iconic spots, so we did just that. 

It was pretty busy in there when we arrived, and I was worried we wouldn’t be able to find a table, but we ended up having no problems at all.  Since Portillo’s specializes in hot dogs (and since Chicago is famous for their hot dogs), Brian and I both opted for a Chicago dog.  They come with mustard, relish, celery salt, freshly chopped onions, sliced red ripe tomatoes, a kosher pickle, and sport peppers on a poppy seed bun.  I had them remove the onions and peppers from mine only because I have a sensitive stomach and I didn’t want to be suffering the rest of the day, and Brian got his the way it came minus the onions.  Jacob opted for spaghetti and meatballs, and Olivia got a cheeseburger.

My thoughts about the Chicago-style dog?  It was okay, but I wasn’t super impressed.  I mean, it was good, but it was really weird that they put an actual pickle on it.  I prefer traditional relish.  And also, I know this is BLASPHEMY in Chicago, but y’all, I just have to have ketchup on my hot dogs!  I am from the south, and in the south, we put mustard AND ketchup on our dogs.  ;o)

Portillo’s is also known for their milkshakes, so Brian and the kids each had one of those – vanilla for Jacob, chocolate for Olivia, and salted caramel spice cake for Brian.  I did have several sips of Brian’s and it was gooood.

After we left Portillo’s, we grabbed an Uber and had him take us to the train station so we could go see our very first sight on our trip… THE HOME ALONE HOUSE!!!!

Y’all!!  Home Alone is one of my all-time favorite movies.  My brothers and I grew up watching it constantly.  My younger brother (the one who is closest in age to me) and I saw it at the movie theater when it came out (my littlest brother wasn’t even born then), and we have watched it hundreds of times over the years.  We would watch it all year long – spring, summer, fall, winter – when we were little, and we can quote nearly the entire thing from start to finish. 

When we were planning our trip, I told Brian that there was no way I could go to Chicago and not see that house, even though it’s a bit of a haul from the city.  So that was the very first thing we set out to do on our trip and I have zero regrets.  It was everything I hoped it would be!

When we arrived at the Metra station (it was not the L train as I mistakenly said in my Instagram story… thank you to one of my Instagram followers for politely correcting me as I don’t want to be giving misinformation!), we had just missed the train, and it appeared that another one wasn’t coming along for a whole hour.  Thankfully, we decided to doublecheck with someone who worked there, and they showed us that another one was leaving in 30 minutes, so we bought day passes and boarded. 

The Metra trains are double-deckers, so naturally, the kids wanted to sit upstairs, and I have to say that was a great decision because you could see so much from up there! 

The Home Alone house is in a neighborhood in Winnetka, IL, a little village in the suburbs of Chicago, and it was the 11th stop out of Chicago.  The train ride was 38 minutes, and then the house is just a 0.3 mile walk through the quaintest little town square from the train station. 

Y’all, it was totally worth it to see this iconic house from one of my favorite movies ever!  When we walked up to it, I totally teared up.  I still can’t believe I got to see it in person.  It was everything I hoped it would be despite the fact that some changes have been made to it over the years. 

For those of you who are interested, the garage on the left side of the house in the movie is no longer there, the circular driveway is gone and has been replaced with a standard driveway on the left side of the house, and there has been a black iron fence installed, likely to keep people from walking on the property.  So while it looks mostly the same as it did in the movie, there have been some little tweaks here and there.  But just look at it... can you even?!

Considering this movie is now 34 years old and considering it’s a little bit of a haul from Chicago, there were still people walking up to the house and driving by constantly to take pictures of it while we were there.  And we were there for about 25 minutes.  And the house is on a regular street in a regular neighborhood and people live there (it’s not a museum or a touristy town), so it is just wild to me that people are still visiting it so often 34 years later.  Haha.

We were there right around the time that school was letting out, and it was a gorgeous fall day – perfect, in fact – sunny, cool, and crisp, so there were kids running around everywhere.  Many were riding bikes, many were walking on the sidewalks, and from the looks of it, it’s just the sweetest, safest little town.  It looked like something out of a movie – it literally is something out of a movie, haha – and I told Brian I’m ready to move there!  From the well-kept houses with tons of charm, the big trees filled with fall leaves, and the kids running up and down the streets and sidewalks, the area is seriously such a dream!  The house next door to the Home Alone house is for sale, so I guess that’s our sign that it’s time to move to Illinois!  Haha.

As we were leaving the house (and after we took a gazillion pictures and videos), a van drove by that looked just like Harry and Marv's van – LOL – and we were all tripping out!  The van was white rather than baby blue, and it wasn't a plumber, but get this... it was a Christmas lights stringing company!  Hahahaha.  Perfection.  We'll never forget our Wet Bandits sighting!!

We walked back to the little town square after that, and I just fell head over heels for Winnetka.  There was a little toy shop that the kids wanted to stop in, but unfortunately, it had just closed, so we walked to the little coffee shop on the corner – Hometown Coffee & Juice – to take a little break and get some waters. 

Hometown Coffee & Juice is the cutest little place with an espresso bar, cold pressed juices, and tons of tea and smoothie options + they have bagels and salads and various types of toast and really yummy treats.  We just grabbed some waters since everyone needed to stay hydrated after our flight and all of the walking we did, but we did sit in there for a bit to soak it all up. 

On one of the walls, they have a little bulletin board where they have pictures of all of the local dogs in their little town and I thought that was just the cutest thing ever.  It was seriously the quaintest little town square, and I didn’t want to leave.

We wanted to make it to the Sears Tower AKA Willis Tower observation deck before dusk, though, so we knew we needed to get back to the city, so we made the short walk back to the train station and jumped on the first one that came along that was headed back to Chicago.  When we got on, the train was full and most of it was students from various private schools in the area (so weird to have to take a train home as a kid, right?!) but we were able to walk from car to car until we finally found some empty seats upstairs.

The ride back was uneventful and quick, and I talked to my Momma on the phone for a lot of it because I was just bursting to tell someone about Winnetka.  Haha.

When we arrived back in Chicago, we walked to the Sears Tower (it’s so hard to call it Willis Tower now after it was the Sears Tower for so long), and we were able to get right in for the observation deck, no waiting for tickets or anything.

They have a bunch of really cool stuff to see on the way to the elevators, so we stopped and took pictures along the way, and then we had to wait about five minutes to get on the elevator to go up.

The observation deck is on the 103rd floor, and the elevator ride is SUPER FAST – I think it was only about 60 seconds long – and the kids finally both learned how to pop their ears on the way up.  Neither of them have been able to pop their ears on command, which has made Olivia a little uncomfortable on flights (since she wouldn’t wear her Earplanes), so I was happy they finally both figured it out.

Sears Tower is 1,353 feet in the air, making it officially the tallest building that we’ve ever visited, and the views were spectacular as you can probably imagine.  This was my first time ever seeing any of the Great Lakes, and it’s just wild to me how Lake Michigan really does just look like an ocean. 

We ended up timing our visit just right because we were able to see the view from daylight until total darkness, and the nighttime city views were incredible.  They had a massive flipping sequins wall where you could “leave your mark in the sky,” so the kids wrote their names and I drew a heart (surprise, surprise) and then, of course, we had to document it with some pictures.

Sears Tower has glass floor walkouts, and there was a bit of a long line for those, so we went back-and-forth about whether or not to wait in line, and ultimately, we decided to wait.  I had originally told Brian I was okay with skipping it since we’ve already done a glass floor walkout in NYC, but I’m SO GLAD we didn’t because we ended up getting to take our pictures at night with the city lights shining below us, and that was quite an experience!  We did our glass floor walkout in NYC during the day, so it was nice to have a completely different vantage point.

We ended up waiting, maybe, 30 minutes for our turn, and they only give you 90 seconds on the glass, but we were able to get all of the pictures that we wanted to get, and then I couldn’t resist buying the professional photo that they took of us when we first walked out there.

Stepping out on 1.5 inches of glass with the city 1,353 feet below you is definitely unsettling, but thankfully, I did okay with my vertigo.  When we went to New York City, Olivia was terrified to step out on the glass, though I was able to get her to do it eventually for one picture.  But on this trip – fearless!  She walked right out there and even took pictures by herself.  Growth.  <3  And Jacob wins for best picture of the night!  He wanted to lay down!

Once we were done there, it was getting late, and we were all starving and ready for dinner.  We snapped a few more pictures of the sky line, headed back down the elevator to the ground floor, the kids bought hot dog souvenirs because – Chicago – and I bought the pictures from our visit (the first three are a green screen and the fourth picture is the real one of us on The Ledge), and then we Ubered back to our hotel.

The first order of business at the hotel was to get all of our luggage and find our room, and we were super pleased with the room.  It was spacious and modern and clean, and it was such a treat to have that much space in a big city since our hotel room in New York City in 2022 was so itty bitty.  We were also on the eighth floor, which was perfect, because I like to be high enough so we don’t hear as much of the road noise, but I don’t want to be high enough to have issues getting an elevator or feel the building swaying.  Haha.  This hotel maxed out at eleven floors so that wouldn’t have happened anyway.

Since it was so late (it was 9 PM our time back home), we didn’t feel like walking or Ubering anywhere for dinner, so instead, we just decided to eat at Osteria Via Stato, the darling Italian Bistro connected to our hotel, and it turned out to be the BEST decision.  We were able to be seated immediately, the service was top-notch, the food was delicious, the drinks were fantastic, and the ambiance was perfection. 

Brian and I started with a round of cocktails – a Sicilian Old-Fashioned for him (bourbon, Zucca Amaro, bitter truth cherry bark, vanilla bitters, and Amarena cherry) and a Stella Bianca for me (vodka, St. Germain Elderflower, white grape juice, and fresh lemon sour) – and we ordered the parmesan garlic bread with pomodoro dipping sauce as an appetizer since we were all starving. 

Brian and I shared the charred pepperoni pizza and a Caesar salad for dinner, and the kids shared a half-sausage (Jacob) and half-cheese (Olivia) pizza.  The pizza was Italian style thin crust pizza – not Chicago deep dish style – and we knew that going in, but don’t worry – we did eventually get some real Chicago style pizza on the trip!  ;o) 

All of the food was incredible, but the parmesan garlic bread might have been some of the best bread I’ve ever had in my life.  SO, SO good.

By the time we were finished there, it was 10:15 PM our time, so we were all exhausted after our early wakeup call and a long day of travel + sight-seeing, so we headed up to our room.  We had to call the concierge for some extra blankets and towels, and then once those arrived, we all hit the hay.

It was truly the best first day, and we couldn’t have asked for more!  Stay tuned for the rest of our trip… I should have those posts up soon!

Happy Monday, y’all!