how I ended up in Chicago one night

So this is a much overdue post of how I ended up in Chicago on the first Saturday in August
It was a long holiday weekend here in Canada.
I knew we (MrDentalSurgeon and I had plans for Saturday night I just didn't know what).
So in my impatience (because we all know I thrive under a plan)...I texted him at 2pm asking if we were still on for that night.

He called me and said, "so umm how about we fly to Chicago for the night, can you be ready in an hour?"
I was nervous but ummm hello Chicago!
So I quickly packed and got ready to travel with him.

1. I totally love traveling with a man.
I think it is so super romantic.
2. I usually dress up to travel because it's fun (and also only when it is a fairly short flight).

Before I knew it we were at the airport going through security.
He arranged for us to stay one of the W's in Chicago because he remembered the W is my favourite!
And as we drove in I was so super excited.

Pic from here.

When we checked in we asked if a city view was possible (who wants a lake view anyway haha?)
Which upgraded us to an awesome room!
I wish I had taken pics...instead I snagged some off their website for you.

We stayed at their city centre one.  Pic from here.

Pic from W hotel site...this totally screams Hello Teagan welcome to Chicago!

Check in area...LOVE

Loved this lobby.

Romantic little nooks!

Loved the dark chairs.

Our room looked like this...I enjoyed the quote thoroughly.

That awkward moment when you agree to one king sized bed.

I seriously LOVE the W hotels.
I ALWAYS have an incredible time.
I can now add Chicago to that fab list that includes...New York, Seoul (Korea), Barcelona (Spain), Chicago...believe it or not I have not actually stayed at the W in Dallas yet!

So the concierge was fabulous as per usual and got us reservations at a steakplace Chicago is known for and a cool new bar that was in the style of a speakeasy.
So we quickly changed.

First we headed to Harry Caray's.
Boasting Chicago's greatest steak.

Pic from here.

We were WAY overdressed.
It was more of a family place with one too many teens in short shorts pouting over their cellphones at dinner.
Here's the entrance into the dining area we ate in.

Pic from here.

At least they had tablecloths and linens (and not butcher paper and crayons if you catch my drift).
I know I know I can be such a snob sometimes!

Pic from here.

Dinner was good.
MrDentalSurgeon had to excuse himself twice during dinner for long periods because he was having some reflux issues.
Which left me often dining alone.
It's likely because he wolfs down his food barely breathing but anyhow.

After a late dinner we headed to Untitled at about 11pm.
Modeled after a speakeasy.
Thank goodness our concierge had gotten us on the list because there was already a massive line.
Oh yea I forgot to mention Lollapollooza(spelling?) was happening at this time...so the fact that we scored an awesome hotel and reservations anywhere in the city was a miracle in itself (we simply had no idea this was going on until the lady at the concierge desk told us-she could have got us tickets but thank goodness MrDentalSurgeon isn't into things like that-I'm so not an outdoor many hours play in the mud concert kind of gal).

Couldn't tell much from the outside.
But once inside I fell in love with it...

Pics all from official website.

So we settled into the cutest little table beside the stage.
You can see it at the top left of the next pic.


And listened to the amazing band.

This wasn't the exact band...but I can't find pics of the one we listed to.  Which was a female singer, and four guys with different instruments included the ones above!

So we indulged in many cocktails.
I had KirRoyale's (a few too many).
And as we closed out the bar and stumbled into a cab I was having an amazing night.
Until we got up to our hotel room which started to spin.
And before I knew it I was on my hands and knees in front of the toilet.
Not how to make a good impression.at.all.

I was so super humiliated.
In the wee hours of the morning...we made out a lot but didn't take it that far.
I'm impressed he made out with me after hearing me hurl for a few hours before.

Then we got up to go explore the city.
And as I got ready.
I thought I was going to die.
It was different than being hungover though.
It was almost food poisoning esque.
MrDentalSurgeon looked at me and said, "you do not look good".
So instead of exploring Chicago and having fun.
I ended up having to lay in bed until 2pm.
And I was so upset and humiliated.
But I literally could not move or eat or anything.
MrDentalSurgeon went to go grab lunch and brought me back Advil and a Vitamin Water.
And before I knew it we were headed back to Toronto.
At least I didn't puke on the plane.
But Sunday night I had a birthday party of one of the CanadaCrew to go to and I didn't make it because I was still feeling awful.

So that my friends is how you turn an amazing trip to Chicago into a horrible embarrasing mess.
Maybe that's why MrDentalSurgeon is not really that interested...