This adventure was a BLAST. Besides travelling from Vancouver to Calgary for holidays and the occasional mini vacation, it was one of the first times travelling for real on my own. I had a friend living in the city and figured it was the perfect opportunity to check a city off my bucket list, travel and escape Vancouver for a little bit!

My morning started at around 3:30am Vancouver time to get to the airport for a 6:45am flight out of YVR. On my way to Chicago I transferred through Minneapolis, which to be honest I had no clue on the US map where I was (yes my US geography needs A LOT of help). After an hour layover I was on my way to Chicago with one of the newest Delta airline planes, the drop down bins actually dropped down to make it MUCH easier to lift a carry on bag to the bins (I’m always thankful for doing push-ups every once in a while during these moments).

Arriving in Chicago I had a few giggles. I couldn’t even purchase a train ticket without needing help. There were two gentlemen working, who were trying to collect the change out of the machine and asked ‘Ma’am do you need help?’, gave me a little surprise at first because in Canada being called Ma’am is a rare thing. BUT, thanks to their help I made it to the old rickety transit train on my first food stop to wait for my friend! My pre – research for yummy local food joints had paid off!

First stop Artopolis Bakery, Cafe and Agora in Greek Town inside the West Loop. I opted for a Chai Latte and a Kataifi (I had no clue what it was). What a sweet treat! The Kataifi is a combination of walnuts, honey and shredded phyllo (filo) dough. The chai latte had such a rich flavour without being too sweet (even with the Kataifi!), I made sure to let the waitress know it was GOOD. I basically had dessert before dinner, but well worth it.

After meeting up with my friend and getting settled in, we headed to Dimo’s Pizza as suggested by another friend who used to live in the city (recommendations are always the best, thank you Facebook!).

We devoured half a Papas Locas – the special of the day and half an Artichoke Heartthrob.

(I was hungry and lighting was poor, sorry for not the best picture)

But of course my sweet tooth was not satisfied and we went on a hunt for dessert. Again from a friend’s recommendation we walked over to Jeni’s Ice Cream. I often will look for people’s reactions, body language and how busy a food spot is before going in, not always the case for some holes in the wall but Jeni’s had a long line and smiling faces…must be good. And it was!

I kept it simple, cookies and cream ice cream. My friend opted for a black cherry flavour of ice cream! That’s all for Day 1 of my Chicago trip, short and sweet due to a day of travel!

Weather was beautiful that day, just a light coat on and running shoes made for easy commuting and taking transit. I LOVE how flat the city is and a little bit jealous Vancouver isn’t the same. It’s such a bike friendly city and I would have died to ride my road bike almost everywhere, so easy.

Day 2 had a bit of things planned but you’ll have to read to see what I got up to (p.s. it included a good morning sweat).

Travel Tip: ALWAYS bring a reusable water bottle when travelling. Saves you money buying, saves plastic bottles from going into landfills AND you can stay hydrated while up in the air.

Hope you enjoy reading the rest of my adventure!


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