36 Hours in Chicago

There are these two fantastic girls in Chicago that I had the pleasure of spending lots of time with 2 summers ago (and at RIT, of course). But since then the NYC -> Chicago and whole work/life thing has gotten in the way. Last Friday, I flew out early for Thanksgiving in order to get some quality girl time in there! And holy cow was that needed.

Unfortunately Friday morning the airline texted to say that the flight was delayed by 2 hours. Not the best start to the trip but it ended up working out really well because Jon and I got to enjoy a spontaneous date night in Queens before I headed to the airport. We went to Sage’s General Store in Long Island City, a restaurant that we went to for his birthday in June. Had an Ithaca Beer and split a brick oven pizza with caramelized onions, roasted cauliflower, roasted potatoes (slivered) and various cheeses on it along with a 5 cheese Mac & Cheese on the side. Delicious all around and way better than the disappointing snack I was planning on consuming on the way to the airport.

Took off around 10:45 and touched down in Chicago by midnight. It was a quick 25 minute taxi ride to their apartment – decided to forgo the hour and 15 minute train ride after midnight through the city. Despite the 2 hour delay and how late it was, we set right down to catching up complete with wine, goat cheese and pita chips. Best way to kick off girls weekend! Ended up staying up until 3:45 Chicago time which felt like 4:45 to me. Yikes!

Since it was such a short time in Chicago, we had plans to head to brunch on Saturday by 8:30 to beat the rush and make the most of the day. After going to bed at 3:45, the alarm at 7 seemed quite loud. Got up anyway and boy was that breakfast worth it.


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We took the L one stop to Southport to go to Southport Grocery and Cafe a place known for their delicious brunch. Remy and I split a spinach omelet (that was filled with spinach artichoke dip) that came with sour cream mashed potatoes and apple cinnamon stuffed french toast. It was just as amazing as it sounds. The mashed potatoes were so so good that I’d go back just for those.


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From there we spent the next few hours wandering in and out of stores – mostly for warmth!! Did a whole lot of walking around in the old neighborhood that I spent the summer in. It was so crazy to be back and see how many things had changed in such a short time.

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Eventually we made it up to Bow Truss for some warmth and a cappuccino. Basically the whole weekend involved us drinking lots of warm beverages and finding new places to sit around and talk! Absolutely loved this little coffee shop – it was so cozy and the tables were all made out of old letterpress drawers.

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Since breakfast was so big and filling we skipped lunch but wanted a small snack – went to 2 Sparrows for a goat cheese cinnamon roll that Kristin had been raving about. It lived up to her description! So tasty even if the waitress thought we were crazy.

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From there we walked down to Lake Michigan – we were just a few blocks away at the time and I figured it wouldn’t be a trip to Chicago without at least a quick peek at it. I most definitely forgot about the fact that it’s colder right by the water!! Yikes! It was absolutely freezing but we managed to snap a few shots before running off for warmth.

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We had planned to go downtown for the lights festival that was supposed to happen around 6:30. After spending lots of time walking around outside we needed to spend a bit of time putting on warm clothes and defrosting before we headed down.

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However, you try to convince yourself to get out of a warm couch burrito of blankets, hand warmers and friends. Yep, not happening. We ended up ordering a deep dish pizza from the comfort of the couch which was a far better and warmer idea!

We did eventually make it out of the couch burrito to head to Guthrie’s (a bar new where Remy used to live). It became our favorite place when I was there over the summer because of their huge wall of board games. It was disappointingly packed and hard to order anything or even find a table but eventually did a played a few rounds of Jenga and Sorry. Walked a bit further down the street to find a less crowded sports bar. It ended up being an awesome choice because we ran into a ton of RIT alum and it became a big reunion and dance party.

Another late night of around 4 am made the 9am wake up difficult yet again but was oh so worth it. Went to Stella’s Diner just 2 blocks down from Remy & Kristin for breakfast. Remy and I shared again (it’s our habit of wanting savory & sweet and not being able to decide!). We had a breakfast bowl of hash browns on the bottom, roasted veggies, cheese and scrambled eggs and then blueberry pancakes!

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Headed across the street after breakfast to Intelligentsia Coffee for a chai latte – because it wouldn’t have been a trip to Chicago without that! Before long it was time to meet up with my parents and start the 4 hour drive north. Even though it was only about a 36 hour trip there it felt like we got to pack SO many things in and catch up on everything in person. The whole trip had me wishing to either move back to Chicago or just buy plane tickets there every weekend.

Thanks girls for an awesome weekend 🙂


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