24 Hours In Chicago
They say that the best laid plans of mice and men often go awry. Now, I haven’t planned anything with a mouse lately (or ever), but I have with my family, and, to paraphrase Lizzo:
why plans great til they gotta be great?
For example, we recently got to spend 24 hours in Chicago. Having never been to The Windy City before, I had a rough itinerary in mind for us, to maximize our time. I then envisioned coming back and telling y’all about our adventures. Luxurious shopping sprees along the Magnificent Mile. Family photos in front of iconic Chicago landmarks like the Bean and the Michael Jordan statue. Self indulgent visits to the locations of my favorite rapper’s childhood home (Kanye West) and the house where my favorite TV show is filmed in (Shameless). Scenes recreated throughout Chi-Town with the kids from my favorite 80s movie (Ferris Bueller’s Day Off). Potentially, it would be an epic Chicago day tour.
Believe it or not, our 24 hours in Chicago did not go as I thought that it would. At all. Here’s how it went down, to the best of my recollection:
9:00AM – Stopped by the Milwaukee Public Market to grab some breakfast, as part of the final stop on our Milwaukee trip. Planned to then make the almost two hour drive to Chicago afterwards. Arrived at the market, and realized that most of the vendors did not open up shop until 10:00AM. Sat outside the market in our van until then.
10:00AM – Stopped by the Milwaukee Public Market to grab some breakfast as part of the final stop on our Milwaukee trip. It had started to rain heavily while we were waiting outside. We got our food to go, and then headed to Chicago in some occasionally torrential downpours, surrounded by dangerously driving transport trucks. It’s a white knuckle drive.
11:00AM – Realized that the forecast in Chicago calls for rain all day. Realized that we’ll have to call an audible on most of the potential destinations on my agenda. Touring around in the rain with three small, soggy kids is a recipe for a sucktacular trip.
11:50AM – Arrived at our first destination, Water Tower Place, to go the American Girl Store, a giant doll store that J had been excited about visiting for months. Upon arrival, discovered that affordable parking in downtown Chicago is harder to find than Steve Bartman’s whereabouts. Some of the parking signage is harder to decipher than the Bulls’ old triangle offense. Proceeded to drive around aimlessly, looking for a reasonable, understandable parking spot.
12:20PM – Finally find a meter parking spot about two blocks away from Water Tower Place. Walked to the American Girl Store.
12:20AM – Kidding. It only felt like I spent 12 hours at the American Girl Store. We were actually there for an hour, with J loving every minute. If you’ve ever wanted to take your doll to a hair salon, or get your kid the same outfit as their doll, then this is the place for you, by the way.
1:20PM – The rain kiboshed the shopping spree along the Magnificent Mile. Well, the rain, and the price tags at some of the high end shops. Instead, we walked through Water Tower Place and went to Macy’s. It had eight floors in it, and clearance sections galore, perfect for Canadians like us looking to ball out on a budget. Unfortunately, it’s also perfect for toddlers like KJ to run around the store like Walter Payton, and to play hide and seek by himself in the clothing racks.
2:10PM – Back to the car, to make our way to an actual iconic Chicago landmark – the Skydeck at Willis Tower (courtesy of tickets from my good friends at the Skydeck. Thanks again, guys!). It’s about a 12 minute drive, to get there from where we were.
2:50PM – Finally find a parking spot after some difficulties, same reasons as before. We are basically closer to Water Tower Place than Willis Tower. We are at a confusingly worded meter, as well. From it, I conclude that we have until 4:00pm to park there, before Oprah Winfrey would come to take our car away, and give it to a member of a studio audience. My conclusion is most likely not even close to being correct. Regardless, we gotta book it to, and through, the Skydeck.
3:00-3:40PM – the Skydeck was not busy, so we were in, up (a 90 second elevator ride!) and enjoying the 1300 plus feet lookout in short fashion. It really was amazing up there. Spectacular views of the city. Tried to take some pics for da ‘Gram, none of which end up making the cut. For example, here’s a family shot of us on the Skydeck Ledge glass floor. If I look scared, it’s because I was scared. If our family looks short-handed, it’s because B didn’t want to come on the Ledge, for the picture. If KJ looks like he’s so hungry that he had to eat his shirt, it’s because he probably was.
Tried to get the kids to pose like Ferris, Sloane and Cam did in Ferris Buehller. Realized that they hadn’t seen the movie, and didn’t know what I was talking about. Settled for this shot:
In the spirit of the Toronto Raptors’ championship and “We The North”, here is “He The North”, as in I’m way up in sky, rocking a Raps’ hat:
3:45PM – Time to rush back to the car. At one point, instead of running, KJ dropped and starting doing push ups.
3:54PM – Noticed KJ crossing a bridge, with some of Chicago’s majestic skyscrapers in the background, would make for a cute pic. Say cheese, little man!
Thanks, white van, for the photobomb.
3:59PM – No sign of Oprah, so our car is safe. With rain pouring down, we decided to go to our hotel, The Willows Hotel, located near the Wrigleyville area of the city. On the way, a rain-drenched Wrigley Field field was not in the cards, so I did the next best thing – walked around the stadium and took some mediocre pictures!
5:00PM – Arrived at The Willows Hotel. It’s a lovely, smaller, boutique hotel, with an old, old school (think 19th century) feel. B will make repeated comments about how he can’t believe the TVs are so new in such a classic building.
6:00PM – The hotel is in a nice, quiet neighbourhood, so we decided to go for a walk. We end up in a clearance section at a T.J. Maxx, because we are apparently all about discounted stuff from department stores which aren’t in Canada. I have this convo with KJ there:
KJ – I miss you!
Me – You can’t miss me. You’re right beside me.
*KJ runs away, runs back*
KJ – I miss you!
I should also mention that, throughout these 24 hours in Chicago, B had been complaining about a headache. The poor kid kept freaking himself out, and escalating his symptoms via incorrect self-diagnosis. It started off in the morning as the slightest of headaches. Later, it increased to it hurting only when he shook his head violently, as if he was headbanging (note: B had never headbanged before in his life). By the time that we are in T.J. Maxx, he is essentially sulking around the place, thinking that he needs a brain transplant.
6:30PM – K had looked up restaurants in the area, so we start to head out to decent sounding one.
6:32PM – K looked up reviews of said restaurant, and read that the owner was allegedly openly racist. We walk to a different dining establishment (in the rain, of course).
8:00PM – After dinner, we walk to get dessert/breakfast, from Stan’s Donuts.
8:25PM – Back to the hotel. Yes, I realize that this seems early to call it a night for someone who wanted to maximize their 24 hours in Chicago. However, we were tired. Plus B had ‘inceptioned’ me, by planting seeds of doubt in my head about the crime rate in the city (“Hey dad, are we going to get shot in Chicago?“). Tapping out and enjoying the safety of our comfy hotel seemed like a good call.
6:00AM-7:00AM – Pack up, get some continental breakfast to go with our donuts, and check out of the hotel, so we can make the 8ish hour long drive home.
7:00AM – 7:30AM – We followed the Waze App, to guide us. The route that we take is very scenic, along the outskirts of the city. Between the skyline and architecture, it’s beautiful looking, in the distance.
7:30AM – We get led to the “Chicago Skyway”, which is a toll road. We pay $5 US to use it.
7:38AM – Waze leads us off of the Skyway, and onto another road. Huh? That’s it?! I immediately want my $5 US back.
We continued our way out of Chi-Town, until it was nothing but a recent memory. 24 hours in Chicago, done just like that.
Hopefully, a return trip will be in order, in the future, and hopefully, things will go as planned, too.
But, you know what they say about the best laid plans, right?
20 thoughts on “24 Hours In Chicago”
Push ups! haha I don’t even want to do them at home. That sounds like a good 24 hours!
I really want to visit Chicago soon. I know my kids would love it. There is just so much to do!
The American girl store sounds really cool! I’ve never visited Chicago, but Did not know that finding a cheap parking lot can be hard to find ! thanks for the tip !
-The Handy Journal-
Omygoshy your kiddos are hella cute! It’s been a minute since I’ve been to Chi-Town. Sorta sux that it rained there on your visit!
Chicago here we come. Very nice itinerary.
it looks like you didn’t let the weather spoil your day out in Chicago and visited as much as you could. The observation deck looks like the highlight of the trip.
Wish to visit Chicago soon to create lifetime memories!!
I love Chicago, there is always tons of stuff to do over there.
Chicago looks great! I’m from the old continent (Europe) so everything from “Across the pond” seems really cool.
I have been to Chicago twice and I really enjoy eating the pizzerias there! I have to visit the American Store if I ever go back!
I actually have never never been there, but I love to bookmark these! I plan to fly there this month. Thanks!
We totally drag our kids around in the rain when traveling because you never know if you’ll visit again.
Wow this place looks wonderful and I have a dream to go travel in USA someday crossfingers great photos!
Love how you tackled this. You surely maximized time spent with your family. Wish i could visit chicago soon. Haha
Chicago is a great place to visit. I enjoy the rails . One of my all-time favorite restaurants. Fogo de Chão Brazilian Steak House, is located there. Yum!
Glad you enjoyed Chicago. If you are still there or planning your next visit please check my post; https://hackytips.com/15-best-things-to-do-in-chicago-illinois/
Sounds like an action packed day!
Your photo captions kill me.
This is high up on my bucket list!
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