We (and by ‘we’ we mean Dad and Mom) survived the worst
downtown traffic ever, making it in a lot of time for our flight! We enjoyed a quick trip with Porter, complete
with their complimentary wine and chocolate chip shortbread cookies, and made
it to Chicago in fine spirits.
Where we stayed: After a near miss with an Expedia
reservation, we were led to a stunningly large suite complete with its own
kitchenette, a washer and dryer, and a closet as large as a Toronto
bedroom. Who are we kidding, we wouldn’t
cook or do laundry on vacation but at least we had the option to store our deep
dish pizza leftovers and hold our variety pack of Goose Island Beers. The hotel was centrally located on North
Michigan Avenue, a hop skip and a jump from the Bean and all the architectural
boat tours your heart could desire.
What we ate and drank: All the delicious things in the
single American size – triple XL. We had
(the best) pulled pork nachos and craft beer.
We ate something called ‘smears’ which was a lot less gross than it
sounds – and we relished pork belly – fried and fatty. We ate three types of deep dish at Lou
Malnati’s, after scoping out many-an-Instragram account for the best deep dish
in all of Chicago. We had greasy Chicago
mix Garett’s popcorn. JD, Britt &
Sophia spent hours researching the best nearby Mexican place and it paid off in
the consumption of many-a-delicious-taco.
Britt, JD, and Sophia also ate what they say was the best meal – a
healthy vegetarian meal in a hipster restaurant – while Ash ate a boxed
sandwich at her conference (so sad).
What we did: Besides eating and drinking (where the
majority of our time went) – Britt, JD, and Ash started out by seeing all the
(non) touristy sites – the random door of a toy company with a giant monster in
the window – worth it for the photos for Britt despite the freezing cold and
the aforementioned awesome nacho place for Ash & JD. They followed it up with the touristy sites –
the Bean… times 2… or 3, Millennium
Park, Grant Park, Buckingham Fountain (which was actually being cleaned…and not
open, since it was like 0 degrees), the John Hancock building, and Navy Pier
(for JD and Britt, while Ash anxiously practiced her impending conference
presentation). Chicago wouldn’t have
been complete without an architecture boat tour with a hilarious tour guide…
who pointed out, grandly, “And here is the biggest tourist trap – oops! – I mean
attraction in Chicago”, and, “I’ve got two thirds of a pun for you – PU” in
reference to a smelly area of the river.
The three also got last minute tickets for the Bill Burr comedy show at
the Chicago theatre, snagging seats nearly close enough to be spit on and more
than close enough to fear being the butt of his, and the openers’, jokes. We had many drinks to compensate for our fear
and needless to say the comedians were all very funny. Ashley went to an LGBT Health conference and
met some researcher superstars (she’s very nerdy, she knows). Sophia became fast friends with JD and Britt,
solidifying their friendship over a shared love of sarcasm and a tour of the
Art Institute of Chicago. We used our
hotel suite for a Halloween pre-party with the 4 of us plus Denny, Jenna and
her UCLA crew. Britt and Ash serenaded
everyone with their Taylor Swift couples costume, while JD stopped traffic,
Sophia became a wild animal, and Jenna and Denny went back to the ‘90s as Wayne
and Garth. Our pre-part was followed by
fun and games (literally, arcade games) at ftw Chicago. The best part (beyond people taking pictures
of JD’s Halloween costume) was Jenna and Denny’s Dance Dance Revolution faceoff. Our next stop was Boys Town on North Halsted
to a packed bar called SideTrack where we ran into a Shania Twain lookalike who
became Jenna’s best friend. It’s like we
had a maple leaf tattooed on our foreheads – Canadian’s unite!
Lesson learned:
Don’t order Irish coffees expecting them to have Bailey’s – they will be
half whiskey, half coffee, and a little strong for 10 am.
Most random moment: At the arcade on Halloween when we
were entertained with an impromptu Steam Punk vampire strip show – it was about
as awkward as it sounds.
Next up… who knows… we guess you’ll have to stay tuned!

