Chicago Bound Round 2

Hi friends!

Ok, so remember a few weeks back when I predicted how my last trip to Chicago was going to go? If not, you can read about it here. And then you can read about what really went down here.

I thought I’d predict this weekend’s trip to Chicago as well. Last time was with Athena and Ashley, my gym besties from Boston. This trip, I’ll be staying with my college roommate. Aka: we were college boozebags/good times.


Here’s how it’ll go:

Friday, Katie will be picking me up on the Blue Line and immediately, we’ll be:


And then it’ll be one huge blur the entire weekend mostly involving booze, pizza, gossip and laughter. Sorta like a mashup of all of these:


Dance parties.


Weird public antics.


Oh no, that’ll be us in like 30 years.


And then us in 50 years.


What they said.


And totally judging.

And then when the weekend is over and it’s time to go home:


Cant. Wait.


Hi Friends! (and strangers)


I am so happy that Monday is over and done with- it was REALLY hard to go into work this morning because I’m coming off a really great vacation high. Yup, Chicago was just about as good as I predicted in my last post.

I hope my recap even does the weekend justice:

Friday morning, I managed to get through a MASSIVE line at the check in AND an even worse customs line AND security—-in FIFTEEN MINUTES. Hashtag good job, Calgary airport (for once). And on top of that, the plane was actually somewhat luxurious…for United Airlines. I had a good 8 inches of extra legroom and my seat felt reclined when it was in the upright position. Hooray!

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My favorite part of the flight was when the stewardess announced the flight crew as Captain Williams…..and Matt. Cool, so Matt’s flying the plane. Hope he’s good.

I managed to get to Chicago at 9:45, so I had five hours to kill before Athena landed. I wandered for a while before settling on lunch at Wolfgang Puck. I ordered a Shock Top and a roasted beet/goat cheese salad. Everything was good until I found a piece of wood in my salad! I pointed it out to my waiter and the chef opted to replace my meal with another (a kale and quinoa salad)…and comp it! Great start to the vacation, indeed.


Once Athena arrived, we took the train to our hotel to meet up with Ashley. $5 is a pretty awesome deal to get downtown is you ask me! And our hotel was only a couple blocks from the nearest stop. We dropped of our bags and got to exploring– first, to Michigan Ave then to the Signature Lounge in the John Hancock building. The Signature Lounge is on the 96th floor, it’s free to get up there, and the views are AMAZING. Thank goodness we chose to do that on a clear day. And drinks were ordered, duh.


Dinner was at Marcadito, a yummy Mexican restaurant. I honestly could have stayed there forever to try all their margaritas, but we were sticrtly told that patio seating had a 90 minute time limit. WOMP. We made it work, though! A round of margs, 3 kinds of tacos, and guac were easily consumed in about 75 minutes. So, neener neener Mercadito!


We rounded out our first night with a stop in the Redhead Piano Bar. The music was great, only it was a small, undergroundish place and I think there was a large, older wedding party there and it just made it a bit tight and uncomfortable. And the martinis there are STRONG in case you were wondering.


We stopped for one last drink at our hotel bar. I don’t even know how to describe the Crimson Lounge because I’m not sure what type of theme they were going for. There were chairs and sofas of all styles; old paintings everywhere, and lots of room dividers to make it super loungy. I know Athena has one fab pic of us with our butt in a couple of those chairs, but I don’t have it…YET. I will get my hands on it and share it though!


(PS: I took my real camera with me this weekend since I had ZERO internet 99% of the time and I wasn’t used to having to focus with the dang thing. My b)

(PPS: Ashley booked this hotel through Groupon. I read some reviews beforehand and there was a ton of not so good things. Luckily, we had zero complaints as the staff was really helpful and polite, the room was clean and huge, and it was in a good location)


After carbing up,


we headed over to our Bites, Bikes and Brews tour!

10 people showed up for the tour. I was lucky enough to be on safety patrol and rode at the back of the pack to ensure cars weren’t being asses and to make sure we didn’t lose anyone. I aced that job.


And yup, it required I wear a sweet, sweet vest.

So we rode about 13 miles around Chicago with stops for deep dish pizza at Gino’s East, cupcakes at Swirlz, dogs at Murphy’s Red Hots, and beers at both Murphy’s Bleachers and RJ Grunts (more on the drinks to follow in this week’s Winesday Wednesday post!)



The tour was really awesome because we got to see a ton of different things the city had to offer AND we had great weather! I highly recommend this if you have 4 hours to spare and want to get in a bit of exercise with your carb consumption 😉

After the tour, we stocked up on water and snacks and headed back to the hotel to get cleaned up for dinner. Prosecco may have been consumed as well.

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Dinner was at Gene & Georgetti– it was a great old school steak house that didn’t disappoint in the service or the food (and wine!) The three of us ordered filet mignons and they were HUGE!

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We followed our meals with a bottle of wine and a Moscow Mule at Chicago Cut. There were no famous people there, we looked. That restaurant was really cool and located just along the river. I would highly recommend this place for people watching.


We then hopped on the train and headed over nearer to Second City where we were going to try to catch a free improv show that started around 1am. We passed the time until then at a couple bars across the street….and getting snacks at Walgreens. The show was really hilarious and I wish we purchased the tickets for the earlier show because they were all hilarious and great to watch.

Sunday morning we had brunch at Rockit and ohmygod it was delicious. My friend Katie from college who lives in Chicago also met up with us to enjoy some yummy food. Her and I ordered the eggs benedict, Ashley got the banana bread french toast (DIVINE) and Athena had a ginormous omelette. Athena and I also opted for a side of fruit that was the best ‘side’ of fruit I’ve ever had- bananas, grapes, apples, strawberries, pineapple, blueberries, oh my!

I definitely think I need to become a luny who brunches. Anyone want to join me (if you’re not in Calgary, we can totally FaceTime brunch)?



We said goodbye to Katie and wandered around until it was time to head back to the airport. We obviously visited THE BEAN then walked over to Ghiradelli’s for a hot drink.


It seems as soon as the trip began, it was over. I all of a sudden got a huge case of Sunday Blues (and homesickness) and really felt sad. Flying back home is never fun. Except for seeing the dogs..and the husband.

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Sad face.

I am VERY grateful to have such wonderful friends who were able to fly and meet me for a girls weekend. We had so much good conversation (something I miss like crazy pants) and were able to get in a ton of things in such a short period of time-> something I don’t think could get done with many other people 😉

Also, the title of this post was SUPPOSED to be our awesome instagram hashtag for the weekend THAT WE NEVER USED.

Also ALSO, I probably missed a bunch of stuff, but this is the longest post I’ve written in a while for EXCUSE ME for any potential blips. If anything, I’ll have a whole second post on funny things from Chicago. Like how Athena and I thought the city smelled like brownies when we first got there and quickly found it really just smelled like dirt and dumps the rest of the weekend. See? So funny.

Chicago bound

So, guys. I’m heading to Chicago tomorrow BRIGHT AND EARLY to have a stupid-fun weekend with two of my favorite Boston friends, Athena and Ashley. (Kysha, I still love you and miss you and wish I could see you!). Before I go on, I’d just like to add that if anyone will be in the O’hare airport between the hours of 10:30am-2:30pm and want to say hi, you can find me at one of the airport bars  restaurants in either Terminal 1 or 2. Just sayin. 

I have been looking forward to this trip since even before I booked it. I need me some Americanness goodness. I just made that up right there, but I’m pretty sure you know what I mean. I exchanged all my Canadian funny money for some good ol’ US Green and I’m ready to go. This is how I’ve been picturing how the weekend will go:

Right now, I’m like, really exciting about typing this:


Tonight, I will get approximately ZERO sleep in anticipation:


Tomorrow morning, I’ll board the plane (with sunglasses in tow. I don’t mess around if I get the sunrise side, knowwhatimsaying)


Then promptly arrive in Chicago and wait for Athena’s plane to arrive. 


And yeah, I’ll probably get stuck next to some super sketchy person. yay. And when Athena and Ashley arrive:


REUNION! hoooooo-ray. I’ll whip out my American money and put on a pair of my new jeggings and we’ll go for a drink/dinner and I will sit there is sheer happiness.


And our hotel will make us all feel like we’re college roomies except there won’t be pillow fights but there will be snacks and gossip.


And then I’ll probably have a lot of drinks and still be so happy that I’m having a girls weekend that I’ll JUST DANCE.


Saturday will be fun because we will be taking a bike tour. I’m super jolly about this because it’s a bike tour that not only educates you about the city, but takes you to enjoy some iconic Chicago food staples: pizza, hot dogs and beer. My head is already in the clouds.


Then we’ll glam up and hit the town again


Hopefully there’s not too much alcohol consumption prior to this otherwise I might pull this move:


Sunday, there will be brunch


And more Chicago-ing. And having a gay ol time


And then we’ll have to head back to the airport and when they call my flight to board, I’ll be all



So yup, exactly like that. CAN’T WAIT!!