An alarm set for 6:20, I wake up at 5:57. Rosalina’s still asleep, in fact so are the rest for that matter. As I admire the view of the plane parked in front of me and its two neighbors, I take a deep breath and head for the shower.

As I run the water to get it warm, I check on the family, who despite disowning me still keep me in their group chats. Out the front door in 20 minutes, I quickly but quietly fire up EVRFREE, reaching Hancock at 6:56.

Sweetie Belle answers the door half dressed and runs back to her bedroom. In about 3 minutes, she emerges with some suitcases. Her parents are still getting ready and her own bags are packed, but Rarity is still asleep. We’ll just pick her up after we drop their parents off. This in mind, Sweetie Belle’s bags go by the front door as we wait for her parents to finish getting ready.

Once all loaded in the car, we have 25 minutes before morning rush and no time to lose. Since they’re flying Spirit, I race to Terminal 3, where upon arrival, a busload of coaches block me in and begin unloading. I sigh in exasperation as I unload their bags. Once all their bags are offloaded, I exchange a handshake with Magnum, a hug from Betty, and snap a picture of the three of them at their request right before they head in.

Thankfully, some of the coach passengers clear a path for me, and so when I clear them, I punch the throttle and get the heck out of O’Hare. Kennedy is still kind to us, but once we meet Edens, I hit the brakes at the Addison/Kimball bend. Not quite a sea of red, but enough to be red on the maps track. To avoid local exit congestion, I try for the express lanes, which should be open if they aren’t already for traffic inbound to the city.

After some aggression to get into the left lane, the next opening beckons, and I take it, along with quite a few others. I actually manage to reach 70, which I hold for a few seconds before the express lanes’ pace matches the local lanes.

A CarPlay text to Rosalina validates only the Apples up and running, which makes sense, seeing as it’s not even 8:00 yet. Matter of fact, Sweetie Belle has already fallen asleep. I send another text to let me know when everyone’s ready. Most attractions don’t even open until 10, so I’d like for everyone to be ready by 9 so we can miss morning rush.

When we finally reach the city, I stay in the express lanes until our exit. We then pick up Rarity, who is all ready for the day, then get back on Dan Ryan towards I-57, putting my foot hard down all the way to our exit.

Once we reach the airport, I make some conversation with the Apples.

Big Macintosh, a man of few words, exchanges mostly yeses and no’s, so his two younger sisters do most of the talking. Applejack, the elder of the two, shares a nice story about their work, which in contrast to an ever-changing industry still farm the old-fashioned way. After running back to her room, she returns with a sample of her product.

Just as I finish my glass, my heart drops to my stomach, I ice over like an NFL kicker, my heart rate climbs and body starts to tingle.

I let out a suppressed groan and breathe shallowly enough to sound hyperventilated.

“Everything okay?”

“Uh, sure I guess.” I respond desperately trying to appear normal.

“Well, I know we just met and all, but Rarity tells me you have a bit of a troubled past.”

“I never told Rarity that.”

“Maybe it was from Sweetie Belle then.”

“Eh, well. I’m surprised either one of them told you.”

“Sorry.”

“Don’t be. I’m not afraid to admit that I was raised a spoiled brat. Any stories you’ve heard are just me playing the victim.”

“Well, bless your heart, sugar cube.”

“Thanks.”

Applejack can only laugh in response. I start laughing with her but quickly stop. I take a step back, clutch my chest and feign coughs, but as ride it out, I hear only a single sentence.

“Look what you did.”

I remain silent and suppress other voices as I see Applejack start to calm back down. Trying my best to recover before she notices, I lean against a wall and take a few deep breaths. My heart rate is taking off again, and despite no real signs of distress, I only utter out a “bless my heart alright” as the aggravations slowly subside.

Applejack though gives me a confused look and asks, “You okay? You seem a little off.”

“Really?” I squeak out nervously. “*ahem*, I mean, what could be better? I’m spending the holiday in good company, I’m living my childhood dream, and have been able to enjoy every minute of it. Why would I have a reason to be off?”

“Well, ya’ seem nervous for starters. Pardon me for askin’, but have you been… uh, abused?”

“No. I grew up the envy of all who knew me. Spoiled rotten from a young age, disciplined a fair amount. I had my rebel phase, drove myself to near suicide, and out of it came an airline pilot with a chip on his shoulder, an albatross around his neck, and the jadedness of a pensioner. Why ask?”

“Behavior raises some curiosity. More than just simply being nervous.”

“I realize I’m in no position to even act like I’ve been dealt a bad hand, because I haven’t by any means. Still though, I feel like life has screwed me in more ways than I would’ve ever imagined.”

“I know how ‘ya feel. When my parents died, I thought I would never be able to run the farm. Big Mac and I worked hard, and though it’s no picnic, we still get to enjoy ourselves.”

“That’s nice. I’m very happy for you. If you don’t mind me asking, when did your parents pass?”

“I was 10.”

“I’m so sorry.”

“Me too. I miss ‘em more and more every day.”

“I’m sure. I miss my family too.”

“Applejack?” A voice calls from the walkway.

“Come on in!” I say.

“You want to join us for a morning walk?” Granny Smith asks.

“Oh, yeah. Let’s go. You wanna come, sugar cube?”

“I’ll pass. I have to move airplanes around.”

Applejack only chuckles as we head out to the ramp. Rainbow and Scootaloo are throwing a football outside as all four Apples head outside with me. Before I reach the Tug, I call my restaurant in town to cater for us, since I’m a terrible cook, and I could never cook for such a large party.

N318AS is staying here, and instead N925VA will make the journey back. As I push the former plane back, the game of catch outside is directed my way. As soon as I see the ball thrown, with clear intent to include me, I’m left with no choice but to stop the tow and watch the outcome. You can imagine how terrified I am of causing a nasty accident, especially with an airplane under tow.

Rainbow Dash catches the pass and jumps onto the passenger seat in one fluid motion, crashing into me and almost knocking me off my seat as Scootaloo excitedly runs towards us, high on excitement from having witnessed an epic play.

“You wouldn’t mind if I, uh, joined you for a joyride in one of your rigs, would ya?” Dash asks high on adrenaline with the blush and heavy breaths to show for it.

“Don’t you fly F-18’s?” I respond, silently wishing I had an enclosed Super Tug with me.

“Yeah?”

“Prepare to be disappointed then.” I respond taking the tug out of gear, which makes her face drop. “Hehe, I’m just kidding. One of these days, definitely.”

She then squishes her cheeks and squeals out, “so. Awesome!”

After I make the switch, I head back to the terminal. The Apples are having a conversation with Dash and Scootaloo, Fluttershy and Rarity are both on their phones. Sunset? Where’s she? A quick check of rooms leads me to assume that she’s asleep. As if she hasn’t established herself as a late riser already. Once I figure out what to hit and when, I count my money and decide to tackle MSI, since it’s the farthest out of downtown.

When the last of us are ready for the day, I call everyone to the ramp and make an announcement to kick off the festivities.

“Good morning everyone. Thank you for joining us. Credit is due to Miss Rarity for getting me in touch with all of you.” I pause as Rarity acknowledges my comment. “My name is Split Scimitar. You may know me as “The Captain,” but you can just call me Max. I admit I don’t have a firm itinerary planned, since I don’t know how many of you have been to Chicago. However, we can remain flexible by choosing our stops around how the day plays out, rather than stick to a rigid schedule. There are three cars for the fourteen of us. We will need a driver for the third one. Any takers?”

None. Most of them kind of shy away, so I then introduce some counterpoint.

“You know, the four Apples can take one car.”

Applejack speaks up with, “well, I guess we can.”

Rosalina offers them the keys but Applejack declines and says, “why don’t you drive us?”

Rosalina nods as Rarity then steps up and says, “I’ll drive the third car then.”

That settled, the others now begin to choose who they want to ride with. Rosalina and the Apples take DJABBIC, leaving Rarity and Sweetie Belle to choose their companions as I give them the keys to LANGKA.

After about 2 minutes, I end up with my two original passengers from Seattle plus Twilight and Pinkie, as the two duos - Rarity/Sweetie Belle and Rainbow Dash/Scootaloo, elect to travel together.

“Alright! Looks like we’re ready to go. I catered dinner tonight, which we’ll have around 18:00. Best we beat the evening rush on the way back here.”

Right before Pinkie climbs in, Rarity stops and says, “Pinkie, why don’t you drive? You’re more of a local than me.”

“Okie dokie, Loki!” She says as she jumps right out, leaving me with Sunset, Fluttershy, and Twilight. They hop in and I tell them, “first stop, MSI.”

When we reach our destination, I head for parking and check out lines. About a 20 minute queue, I group text the drivers to meet at the front entrance while I grab the tickets. Only three spots ahead of me, I make a group purchase and give everyone their ticket.

“Alright, this is the Museum of Science and and Industry, easily one of if not my favorite museum out there, but I’m also a technology person, so that’s probably why. Some of my favorites include the transportation exhibit featuring a Boeing 727 in the ceiling and The Great Train Story, if you grew up with Thomas the Tank Engine like me. Let’s meet back here in about 3 hours. Beware of some exhibits that charge extra for entry. Just request a receipt if you want to see it so I can reimburse you. Have fun!”

Rosalina decides to stay with me as I in a complete surprise stay in the Boeing ship and listen to some chatter about airplanes. I laugh as some of the youth chat about being a glorious pilot. News flash kid, it ain’t all it’s cracked up to be.

Even though the cockpit is sealed off, I admire the flight engineer’s panel just as a small crowd comes aboard. I quickly escape to rejoin my childhood staple: The Great Train Story. As I interact with the exhibit, I smile contentedly but am stumbled by yet more heart palpitations. Deep breathing doesn’t work, and a trip to the watering hole doesn’t help either.

When Rosalina leaves to explore other exhibits, heart palpitations give way to an overall tingly feeling that fades into acute numbness. In fact, by the time I circumnavigate the museum floor, I take a seat shivering in terror. As I try to clear my mind, I head for the bathroom and clutch my chest as I reach a handicapped stall because the tingling has spread beyond my chest. Eventually, I start to convulse and collapse onto the bathroom floor, struggling for air as my vision starts to go.

As my vision goes white, I punch the throttle and climb above the cloud tops. When I fully recover, a few people are crowding the stall, so I get up as quick as I can. Some people give me dirty looks, but as soon as I exit the bathroom, I literally run into Fluttershy, who blushes heavily and apologizes as I do.

As I insist it wasn’t her fault, a shooting pain of skin-tearing proportions shoots up from beneath my sternum. I writhe in agony and collapse to the floor again as Fluttershy squeals. The sound of my thud surely attracts a crowd as Fluttershy tries to help me.

“Max! What’s wrong?!”

“Don’t know.” I slur out. “I’ve got a shooting pain in my chest. Out of nowhere. Get me some water and a cola.”

“Okay…” she responds as she runs off.

A security guard soon helps me up and asks what happened. I half-heartedly explain that I tripped over my shoelaces, which he somehow buys, since my shoelaces are loose but far from undone. He soon leaves and reminds me to be careful just as Fluttershy returns.

“Here’s your water, and your coke.”

“The coke is for me. The water is for you.” I say as I present her with a $20.

“Oh, thank you.” She says blushing.

“We’ve only been here… 2 hours?” I say taking a sip. “Anything else you want to see or do?”

“Um, no. Unless you do.” She responds timidly.

“I’ve seen most of these exhibits a handful of times already. What’d you see?”

“I stayed mostly in the genetics lab because of the baby chicks.” She says with a blush.

“They are cute aren’t they?”

She nods brightly in response.

“Have you seen the others?”

“No. Not since we got our tickets.”

“Oh well. If you’d like, we can head back to the meeting point anyway.”

“Okay.”

Sure enough, Rosalina is there waiting for us with Scootaloo.

“Hey! Finished early?”

“Yeah!” Scootaloo responds. “The jet engine was so cool!”

“Yeah?” I respond.

“When are you gonna take us up?”

“One of these days.” I respond as Twilight and Rainbow return. I ask what they did: while Dash had a Ball at Science Storms, Twilight excitedly gives a brief synopsis about Numbers In Nature.

A few minutes later, Pinkie shows up with a toy made in the Fab Lab as well as a top. I reimburse her with a $20 as Rarity and Sweetie Belle tell us about their pursuits in U-505, both mild history buffs. The Apples soon join us and talk about farming tactics vs their choice exhibit on agriculture as Sunset explains her fascination with tornadoes to beat my budgeted 3 hours by about 25 minutes.

After we head up Lake Shore Drive, I point out Soldier Field and Museum Campus for later as we continue up to Navy Pier for a spot of lunch at Billy Goat’s Tavern. Apple Bloom, the only Cubs fan amongst us, gets excited as she bursts out “fries and a Coke!”

Only I roll my eyes having understood the joke.

A fantastic lunch despite some resistance from Sunset leaves us very satisfied. I apologize to Sunset and Fluttershy, our vegetarians, but insist that it is one of my all time favorites in town.

Our next stop is Sears Tower’s Floor 103. Most of the young‘uns are pretty put off by the glass balconies, but Rosalina and I have nothing more than a laugh as I point out views from the Lake and to the rest of the city. My city. The greatest city in the world.

To take advantage of free parking on the other side of town, we head to my personal underground garage at the Chicago Spire. Conveniently located just a few blocks from Hancock and Water Tower Place, I lead a charge to Garrett’s before I show the others my monster penthouse.

As I give them The Grand Tour, who but Rainbow Dash should suggest we just stay here instead, what with there being “more than enough living space for all of us.” I present the idea to the rest of the group, who all approve, unanimously.

After everyone “bids” for a bedroom, I bring everybody to my pièce de résistance, the world’s highest indoor pool. Located on the 300th floor enclosed with greenhouse glass, the place is truly a masterpiece. 2/3 Olympic size, depths of 5 to 15 feet. At the deep end is a 4-tiered diving board with two springboards at 1 m and 3 m, plus two static platforms at heights of 5 m and 7.5 m.

The pool is currently covered and drained, so I ask if anyone would want to swim largely as a joke but on the off-chance someone does. The choice to turn fill the pool rests on our guests.

“Well, I don’t know about any of you, but I can improvise.” Sunset says.

“Whoa there, Sunset!” Exclaims Rainbow with a smug look on her face. “Eager to impress?”

“Shut up, Rainbow!” Sunset snaps back. “You’re just jealous!”

“Alright everyone.” Applejack intervenes. “Let’s not get too excited before the holiday even starts.”

Rainbow then claps back, “you just wanna show off!”

[“No I don’t!”

“Never mind.”](https://youtube.com/watch?v=FhT1jxVX4I4&t=0m26s) I quickly say to calm everyone down. “It was a joke. I don’t need a dimmer station.”

“Demonstration.” Rosalina instinctively corrects, which makes me chuckle.

“I wouldn’t mind swimming though.” Pinkie says.

“No, Pinkie. You can’t skinny dip.” Sunset quips back as if by instinct, to which everyone, even Pinkie, breaks down laughing.

Rosalina chuckles as I facepalm. I then say to the group, “Well, what’s your verdict? If yes, it’ll take a whole day to fill up.”

“Just fill it then.” Pinkie calls back. “Whether we do or not, at least it’ll be available.”

“Oh alright then. Fresh from the Lake, coming right up.” I say as I pull the big lever that initiates the auto fill and retract the cover.

Rosalina then surprises Twilight by inviting her to her condo to show her her library. Twilight’s eyes gleam like a kid in a candy store as she gleefully leaves with her.

Now that we’ve solidified our move to Spire, now comes the fun part, moving out of the airport.

At SMG, everyone cleans out their space at the terminal. In the case of the two cars that drove in, they decide to take their own cars into the city with us. Despite her best efforts, before Rarity can close the back, two suitcases tumble out of LANGKA’s boot. Seeing this as I start EVRFREE, I immediately shut it off after the gauges come alive. I then whisper, “god… damnit” as an enraged Rarity screams, so I go help them out.

Applejack then comes to my aid and pulls all the suitcases out so I can rearrange them. When we finish, Rarity blushes as Applejack and I high five, then Rosalina starts DJABBIC to say she’s ready. After Rarity jumps in and starts LANGKA, I start EVRFREE up again and lead the 5-car convoy to Chicago.

Just as everyone gets settled in their room, I get the delivery call. I meet the delivery man at ground level and make multiple trips for the various trays. Once I tip him and send him on his way, I group text “soup’s on everybody!”

Sure enough, the Apples make their way down first as I open the first few dishes up.

Sure, it’s from a restaurant I own, but nevertheless, it’s a spot on 9.5/10, only because some items have fallen victim to steam soak, or more accurately, condensation sogginess. Nevertheless, I open the food for the taking after I pull out some dishes and silverware.

As we all enjoy our first meal together, I take a step back after everyone starts conversation. I take in the sight before me and join the rest. One who takes a particular interest in me is Pinkie, having saved a seat for me. As she and her group start to pick up speed in a conversation, she grabs my hand and rests her head on my arm. Rosalina sees this and smirks. I flash my wife a look of “help,” but she nods and lets me have this one.

At meal’s end, I bus dishes and load the dishwasher as the city lights take prominence at civil twilight. I let out a small smile as Sunset joins me at my side opposite Rosalina.

“Thank you for hosting us for this trip, Max!”

“You’re so generous for offering your insanely spacious penthouse to all of us!” Rarity chimes in as she searches for a bottle of wine for the evening. After grabbing a chalet for everyone, she selects a Chardonnay perfect from the wine closet for the steak dinner that some of us had, and by some, I mean not Sunset or Fluttershy.

“Speech from Captain Max!” Pinkie exclaims as the last person fills their glass.

I chuckle as the others raise their glasses, so I speak up.

“I cannot thank you enough for taking the time to spend your holiday with us. Credit is due to Rarity, who helped organize this. We still have a few tourist attractions left to visit as well as my own personal favorite eats. I hope that after showing you the tourist traps and some of my favorite local eats, you can see why I love my hometown. Here’s to a great one!”

A chorus of “Cheers!” rings throughout the penthouse as I down my glass like a shot, followed by a swift grab for a second. Rosalina peers over as I gently sip this second one. I let out a sigh as she puts her hand on my shoulder.

“I know you don’t like to admit it, but something’s been up with you.”

“Is it that obvious?”

“Yes. Is something bothering you?”

“I don’t know, that’s the thing. I shouldn’t be. I’ve met new people. Great people. I have no reason whatsoever for anything to bother me. I have no fears for the future beyond what I would deem a healthy amount, my past has no reason to haunt me, and I have you.”

“Hmm.” She responds. “I know I haven’t been everything you’ve wanted me to, but being married to you is the best thing I’ve ever done.”

“You have been everything I could ever want. Please don’t think otherwise.“

“No I haven’t, and you know it.”

“Fine, I admit it.” I respond rather facetiously, downing the last of my glass. “In all seriousness though,” I quickly continue, “You would know if I felt an issue in that department, because I would've said something. There is absolutely nothing else I would want from you. You’re there for me when I need you. You understand that I value my alone time, and are more than willing to respect it. I haven’t seen that in many others. I can’t begin to describe how much you’ve meant to me over the years we’ve been together.”

She eventually walks away, having been rendered speechless and blushing bright red. After the bottle goes empty, courtesy of Rainbow and me, I start the dishwasher as Rosalina kicks me off the sink and does the rest of the dishes. In response, I decide to head to bed early.

Author's Note

The Dan Ryan Expressway is I-90/I-94 concurrent south of I-290, and ends at the I-94/I-57 interchange.

SMG is the airport identifier for the [fictional] Chicago–Gusty Garden Airport.