Windy Dream, The Chicago Free-For-All

Imagine if money WEREN'T an issue.

It's an early Friday afternoon, you're driving up to your significant others place of work and telling them to jump in the car. You both are ready to get the weekend started. You're all smiles and so are they :) The sun is shining, gas tank is full and somehow you beat the afternoon traffic and you just start driving. (Northbound on I-65).

What they don't know is that you have an absolute free for all planned on the other side of your drive... and neither of you have suitcases. It is going to be an all you can think, all you can consume sort of weekend. Nothing but each other and a blank page. You have literally nothing. The most important thing, is you have each other... and a loft on airbnb off Wicker Park in the heart of Chicago confirmed, 2 nights, free Wi-Fi and a keurig.

Once you break the news of your idea there is a glimpse of uncertainty in the air. Not doubt or fear, maybe just a little shock, but neither good nor bad.

How can you be so sporadic? What about the retainers and tooth brushes. What about CLOTHES and shoes? Other than the ones on your back and maybe stowed away in the car you have NOTHING?

My vote is to head over to the nearest Lululemon store and completely outfit myself for the comfortable weekend we're about to indulge in. I'm heading for those perfect falling & fitted tees that make me look much more muscular than I actually am. What about the joggers that have so much stretch I could use them as fitted sheets? Need em too. As for bae, she can't help but get the shorts, skirt and joggers because why not?

What's next? My stomach is very much grumbling from shopping. Does the Chicago theatre serve food? Well if money isn't an issue than neither should serving food. Let's do that. Hamilton, yes let's go see Hamilton! ANGELICA!!!!

After a spectacular performance with multiple rounds of champagne, this convinces a stop by Chicago style Deep dish pizza. Let's pin down a hole in the wall and swoop it up.

After waiting in line, and consuming the pizza within 5 minutes I picture rolling into the bnb, to song and dance in cue and falling face first on the bed. This is where we tune into Schitts creek, Rick & Morty or Friends. We aren't entirely disgusting, so we did stop for toothbrushes and deodorant and the likes...

After a great nights sleep I'm thinking around 9 am there's a search for bike rentals, and an impromptu bike around the city. Maybe a tandem bike?

After the sun burn and sweat sets in, cleaning up for a brunch is definitely the move.

Did someone call Ariana Grande? Because brunch at Tiffany's is now within sights.

Picking out this, that and the other while being served only the finest calls for showing off the new jewels. So walking the riverwalk is the only option to flaunt the bling and burn off the cals...

At the end of the walk, we then hop on the water cruise and get to cool off on the waterway tour.

What is next?

What's next is to enjoy the weather at Wrigley. Our cubbies will be either A.) ready to sweep the cards, or B.) The reds. So we can enjoy a dog, topped with everything and some overpriced beer. Maybe a souvenir like a commemorative Louisville slugger and some jerseys.

How do you finish out a great game? By waiting in line to get autographs because somebody messed up your custom bat in the store so they're giving you complimentary backstage, locker-room equivalent passes. You can't pay for this experience most of the time, so just let the luck keep comin your way.

After the game a quick stop by the room to drop off our things and off for our Saturday night in the city.

I'm picturing a beer centric, live-music place we can both sit back and enjoy the rest of our time together, at least before the caffeine and high from the autographs wears off.

After dancing with the band, poor Karaoke performances and getting to know the locals at the bar, we decide to walk to get a bicycle taxi back and feel the wind in our hair.

Saturday ends the same way as Friday night, but with all new experiences, a massive success. The final Sunday morning is at a rooftop bruncheon, where the mimosas are served in golden glasses and the crepes have shaved gold as if we were at Tiffany's again.

Thinking back on the weekend, and while the money allowed us to do anything and everything we wanted, the best part was being there with my best-friend the entire time. The foul balls landing in the nachos, to seagulls stealing our hat off the river tour, we had an exceptional weekend, all on the spur of a moment.

That is our windy city dream.

Feedback PLEASE! What you would do? Where would you go? Locals, what would you recommend? The best places to visit, tour and stay.

I would actually love to do this and more so any ideas send my way!