ZzzQuil done good, I wake up with enough energy to jump into the shower. Unfortunately, that energy wears off by the time I reach the kitchen. Enjoying fresh tap water, sourced from the only All-American Great Lake, I beat the Apples to the up, but only by a few seconds, as when I finish my first glass, the lift dings, revealing the core four ready for the day.

“I win.” I say. “Good morning and happy holidays!”

“Morning, sugar cube.”

“Happy holidays!” Granny Smith adds. “The night treat you well?”

“Uh, okay I guess. I’m a little excited right now. I have the best Chicago pizza many years running for dinner.”

“I’m still full from last night.” Apple Bloom whines.

“Eeyup.” Big Mac cracks back in agreement.

“Well, then be mindful of tonight. I’ve got plenty of fun in store, mostly food. I get really excited about Chicago pizza, and I’m showing you my favorites. I won’t get to show you the lower end of the pizza spectrum.”

“The lower end of the what now?” Applejack asks more confused than the others.

“Of the four major Chicago pizza chains, I rank them as Giordano’s, followed by Gino’s East and Uno/Due in a close tie for second, then Lou Malnati’s as the best. It also just hit me that Sunset can visit both Lou’s and Gino’s, as there are locations in Phoenix.”

“Oh that’s alright.” Sunset chimes in, appearing behind the Apples.

“Hello Sunset. You’re up early this morning.”

“I know. I just woke up and couldn’t go back to sleep.”

“I hope that’s not a bad thing.”

“Thanks.” She says jabbing her fist into my arm and peeking into the fridge.

“What? I’m just concerned that you might crash in the middle of the day.”

“Maybe.”

Before the next person comes down, I get a call from the restaurant.

“Hello?”

“Hi, is this Max?”

“It is.”

“Hi, this is Lou Malnati’s Lincolnwood calling, how are you today?”

“Very well, yourself?”

“Not too bad. I have you with an expected party of… 15 for tonight’s private event?”

“That is correct.”

“Excellent. Would you like to pre-order your pizzas so that they’ll be ready when you all get here?”

“Um, sure. That way, as soon as everyone is seated, we can grab drink orders and then roll them out.”

“Excellent, one moment please… go ahead.”

“Okay, um. First off, all pizzas will be large. Just to keep things simple.”

“Sure.”

“And to keep things simpler still, two of each deep dish pie.”

“Two Lou’s, Two Chicago Classic, and Two Cheese?”

“Yes. Six pizzas in total.”

“You want to throw in anything else?”

“Um, a few orders of the garlic cheese bread.”

“You got it.”

“And that should complete the order.”

“Alright, 2 Lou, 2 Chicago Classic, 2 Cheese; and is 3 good for the Garlic Cheese Bread?”

“That’s all correct. Can you hold for one second?”

“Yeah, no problem.”

“Thank you. One moment please.”

Placed on hold, I wait patiently for the other end of the line.

About three minutes later, the music cuts.

“Hello Max, you still there?”

“Yes, I’m here.”

“Would you like to do an open bar? I have my manager here with me. He can talk to you about that.”

“Sure.”

“No problem, one moment please.”

“Hello?” Another voice responds. “Is this Max?”

“Yes sir.”

“Okay. Um, you want to do an open bar?”

“I’d like to just in case, but I don’t know if they’d want to or whether they’d actually use it.”

“It won’t be a problem either way.”

“What cancellation rate is there if we decide not to?”

“Nothing extra. We’ll only charge what you buy.”

“Okay, then we’ll go ahead and do that.”

“You got it!”

“Thank you so much!”

“No problem. Now, let’s just make sure everything is correct. You’re set for 19:10, 2 Lou, 2 Classic, 2 Cheese, 3 Garlic Cheese Bread, and open bar.”

“Uh, yes.”

“Sounds good. You’re all set.”

“Will this interfere with company picnics or family times?”

“Actually, no. The staff on duty tonight volunteered for it.”

“Well, I wouldn’t want to intrude on their time. If I may ask, what’s the overtime pay for this shift?”

“Time and 3/4.”

“I’ll raise you to 2. Consider it extra gratuity.”

“You’ve got yourself a deal. My staff will be very grateful.”

“Perfect. Will I be seeing you tonight?”

“Not me, sir. My parents have invited us to their house in Palatine.”

“No problem. Safe travels and happy holidays to you!”

“Thank you sir, same to you.”

“Thank you. Bye now.”

“Bye.”

Since our only plan is Lincolnwood at 19:10, out of the city at 18:05. Until then, breakfast, ideas, and see where we go from here.

Dishwasher loaded and on a delayed start, I propose, “anywhere you want to go? I know Au Cheval was a request.”

“They open on the holiday?”

“It’s a bar. I don’t see why not.”

“Let’s go then.”

“Dinner isn’t until 19:00, so we can eat there at around 14:00. Is there anywhere or anything you want to do in the meantime?”

“Uh, do you want to walk around Magnificent Mile?” Pinkie suggests.

“Anyone want to go shopping?” I ask everyone.

“Same place as last?” Sunset asks.

“Pretty much. It’ll be on Magnificent Mile, of which Water Tower is a part.”

“Why not?” A few respond with uncertainty.

“There’s Zara, Saks Fifth, Nike, Cubs store, Neiman Marcus, Tiffany, Rolex, Cartier… uh, that’s all I can think of off the top of my head.”

“Works for me!” Pinkie exclaims.

“And I must simply NOT let a trip to a place such as this one go without a trip to Tiffany!”

“Never took you for a Tiffany girl, Rares.” Applejack quips with clear intent of provocation.

“Oh, pfft, Applejack, don’t be absurd!” Rarity scoffs back, which makes the blonde chuckle.

“Any takers for Magnificent Mile?” I ask one more time.

Sunset, Rarity, Pinkie, Sweetie Belle, Apple Bloom, and Fluttershy all oblige. The rest of the group eventually concurs, and seeing it as an opportunity to at least, in the words of Granny Smith, take a walk to get out of the condo, we pile into the lift.

When we get to Michigan Ave, I stop at Intercontinental, designating Michael Jordan’s Steakhouse the rendezvous point at 13:00. Rarity, Sunset, Pinkie and Fluttershy make for the shops as Rosalina decides to take Lockie to MJ’s for lunch. Granny Smith takes her grandchildren for a walk, and Apple Bloom convinces her two besties to join them, so Pinkie, Rainbow Dash and Twilight join the 3 of us for a light meal.

Being Michael Jordan’s Steakhouse, I tout the Delmonico but highly recommend pretty much everything else on the menu. I admit, we should’ve made a reservation, so after consulting with our waiter, I warn that we have many others coming in from Magnificent Mile. After talking with the hostess, we get moved to a bigger table that’ll fit us all, with the same waitress.

Not 15 minutes after we order, the first shoppers return. A quick peek at the hair reveals our trend-setting fashionista. In one hand is a single midsize bag, bearing the likes of Tiffany. No surprises there, I try and peek inside the bag, but instead of snatching it away from prying eyes, she reaches into her top and pulls out a beautiful necklace she’s wearing that complements her decidedly wintery outfit.

I give her beady eyes as a joke, to which she immediately reacts with, “stop staring! That’s not very becoming of either of us, especially for you!”

“Pardon me for admiring a very pretty design.” I say in my defense as she blushes.

When a few more join us, I pass the Delmonico steak I ordered around. Each of the others takes a bite except for the obvious, leaving two more bites for me, which I finish easily.

After I close the tab, we return to Spire, swap some things, then pile into cars for Au Cheval. North Water–McClurg–Grand–State, across Bataan-Corregidor, to Randolph. Scattered parking for the three cars, I grab the table as soon as I park. Largely open seating, 3 booths of 5 apiece should fare well here. The service is surprisingly slow, even for a holiday.

A waitress/waiter team, the latter in training, handle us for the afternoon. After plenty of suggestions, each table will split a burger, to be sensible. With only one other party here, we go through drinks, glad that Applejack is at another table, so I have a single shot of Chocolate Martini and nothing else besides water and coffee. When the last bits of burger are whittled down, I close the tab amidst a few lively conversations from our other tables. With still a few hours before Lou’s, we return to Spire and ready our stomachs.

When we roll onto Kennedy, traffic is pretty heavy, especially because winter is coming late this year. Nevertheless, I play it aggressive and maintain an average of 86 until we reach Edens, where the speed of our convoy matches the highway number - 94.

Hot brakes at the Touhy off-ramp, we grab good spots due to being the only ones here besides employees.

The pizzas and garlic bread are already there, and so after the whole group plays dibs, we all gather round for the pizza. Each person grabs a slice to kick things off. Just as I expected, a few keep their dinner light. In fact, the heaviest eaters are Rainbow Dash and Applejack. No surprises there, I spend most of the evening joining in the occasional conversation, watching the drinks tab rack up all the while.

The dinner itself kind of goes late, with plenty of leftovers. At this point, I ask for the check. A hefty tip and gratuity for the 2 times overtime bonus yields a total dinner cost of $405.91.

After the last of the food gets boxed up, I carry plenty of leftovers back with me for the night. Back at Spire, I decide to dip my feet in the hot tub, where I’m joined by my wife. I chat with her for the brief time she stays, but after a goodnight hug and kiss, she quickly leaves to take Lockie to her place.

A few minutes later, I call the lift back to get me. When the doors open, Apple Bloom is standing inside the car.

“Hi Max!”

“Howdy Apple Bloom. You look unusually energetic for thanksgiving… midnight.”

“I’m not a Black Friday type, and I still have some energy left. Figured I may as well hang out up here.”

“You have swimwear?”

“No, but a few laps won’t hurt.”

“Fair enough. Have fun, but no skinny dipping.”

“Thanks!” She responds as she takes off her clothes, jumping in the pool as the lift doors close.

Back at the lobby, Sweetie Belle and Scootaloo are comfortable in front of the tv, watching a movie. I smile at the two of them as I head for the master. My evening routine exhausts me perfectly to bed, so I declare this holiday gathering a success!

Next morning, I pour some cereal to finish the milk, joined by Rosalina, Lockie, Twilight, and the Apples.

“Lockie, when do you leave?”

“16:45.”

“Cool. No one else is leaving today, right?”

“We weren’t planning on driving back until tomorrow.” Applejack answers.

“Same here.” Twilight says.

To my surprise, Rosalina pulls me aside and says, “I know it’s such short notice, but Lockie needs me to go with him.”

“Do you need me with you?”

“Not really. We need to go through our parents’ stuff since he needs to free space at his house.”

“Oh. How long will you be gone?”

“I can’t say. There’s supposedly a lot of stuff to go through.”

“Would you care if I was with you?”

“It’s fine if you do, but you don’t need to.”

“No problem if you don’t.”

“I don’t think you’ll need to be there actually. I will however let you know if I do need you.”

“Yes, please do. Same flight as Lockie then?”

“Yes.”

“No problem.“

Soon, everyone is ready, and as a treat from my own Chicago trips, I set course for Affy Tapple. A real treat for our farmers, featuring, nutty, plain, M&M, you name it. One of everything? Sure.

While the others enjoy their Caramel Apples & Apple Sweets, I make a quick stop at Oberweis because I’m the only one crazy enough to get ice cream in a Midwestern winter.

Once we return to Spire, I delay the drive to Midway by 25 minutes since we have some extra time. I ask if anyone wants to join, but only Applejack accepts.

Once we pile in, everyone wishes each other well, and bags loaded, I head for MDW. Stevenson gives us some trouble, but Cicero really gives it to us. No surprises there, I soon reach the departures loop, finding just enough space behind a departing car to drop them off.

I make quick work of unloading, and as soon as I close the boot, I give hugs and kisses as they head in to check their bags. After they join the long queue for baggage check-in, I climb back in and traffic check, to which a guard clears me in to a line of slow-moving traffic out of terminal loop.

As soon as I get onto Stevenson, I get a text from Rosalina. I open it to see what she says, and CarPlay announces,

“I want a divorce.”

Author's Note

Thank you for sticking with me to the end. I had some fun with it, since this is loosely inspired by events that happened to me spending the holiday with two sides of my family that are virtually at war with each other. Me having to play the middle man and getting flack from my parents and siblings for even associating with that side of the family really threw me for a whirl.

I am a proud Chicagoan. My previous fan fiction work in the other 2 universes I’ve worked with - Disney and Nintendo, have a significant Chicago story within them. Now it’s MLP’s turn. Writing this helped alleviate some of the tensions from my panic attacks, which is reflected in the way it’s written.

Individual adventures on the way!