48 Hours In Chicago: Vlog + Travel Diary

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I went on a quick trip to Chicago recently with my friend David (@popspaceballoons) to work on one of his projects.

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The last time we did a trip it was to Vegas so it was super quick since it’s so close to LA. We were traveling a little further this time and we both have busy schedules but we managed to add an extra day to this trip. So instead of 24 hours in Vegas, i present to you 48 hours in Chicago.

Pequod’s Pizza

The first stop we had to make was at Pequods’s Pizza. We took an Uber straight there after landing. I have to admit I didn’t do much research before coming but David had us covered. This place is famous in Chicago for it’s dip dish pizzas and even though I recently gave up dairy, I had to cheat a little! It is famous after all! We got spinach and black olive on ours. I wish I could have trie different combinations but there’s only so much my stomach could fit. After one hardy slice, I was full! We had to take the rest home.

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After Pizza, we checked into our hotel, Millennium Knickerbocker Hotel on the Gold Coast. It had an older vibe as it was built in the 20’s but I liked that about it. They still had the old school concierge that waits outside on the curb to hail you a cab and a traditional suited bell man. It was a nice change from the boutique hotels I have been staying at lately.

After checking in and getting settled we decided to explore a little. First stop was MOCA.

MOCA (Museum of Contemporary Art)

This is a very small museum. I didn’t know what to expect since David planned it so I didn’t have any high hopes but it’s definitely a quick run through. You can do the whole thing in well under an hour. We were told afterwards that the Art Institute Museum is the museum to visit in Chicago. It was too late for us to go by then but I’m bookmarking it for next time!

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After the museum we visited The Bean and the surrounding exhibits in Millennium park.

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We randomly stopped in a restaurant called Lyfe Kitchen for a light bite before we had to meet David’s friend. We were pleasantly surprised by the corn chowder. Perfect for the chilly Chicago weather. It was high 40’s in May! That’s colder than my hometown Boston so I was not used to that.

After a quick stop to our hotel we walked over to the John Hancock building to have drinks on the 96th floor.

The Signature Room

This restaurant had THE BEST view of Chicago. I can’t speak to the cocktails cause we kept it virgin since we had to wake up early to work the next day, but it is completely worth it for the view. We even caught the most EPIC sunset. Best time to go is during sunset, hands down. (check my video to see the time lapse sunset) There is a restaurant on the 95th floor and drinks/lounge on the 96th. Apparently it’s more of a touristy place but I’m a tourist so hey!

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Girl and the Goat

We finished the day off at Girl and the Goat, a restaurant a friend recommended. Normally it’s booked for weeks but David managed to get us a reservation. Chicago is apparently a foodie town and even though we didn’t have time to eat a million places I’m so glad we got to eat here. The food was AMAZING. The goat empanadas were my favorite, I’m seriously dreaming about them now. We also ordered the pan roasted halibut, which was also really delicious, roasted cauliflower, wood grilled broccoli, and the green garlic potato pierogies. Everything was beyond good. They also separated the menu by Veggie, Fish, and Meat which I thought was clever. The ambiance was spectacular and I loved the neighborhood it was in. Definitely book a reservation here if you are planning a trip to Chicago!

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The next day we woke up early to get a head start on the installation and of course breakfast! It was kind of weird David make reservations at a bbq place for breakfast but it ended up being so good!

Southern Cut BBQ

We ordered the Grilled Avocado Caprese Crostini and the Vanilla Brioche French Toast and split them so we could try both. If their dinner is as good as their breakfast then it’s probably ridiculously bomb. Breakfast is my favorite food and they definitely didn’t disappoint.

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After breakfast we headed to the McCormick center to build the installation. It took us about 4-5 hours and hundreds of balloons but it was our second time doing it so we were more efficient this time around. We ended up leaving with a little more time to explore so we headed to Sky Deck cause I had been dying to go after seeing all the pictures on Instagram.

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Sky Deck

The sky deck is over 1700 feet up in the air (much taller than even the empire state building!) where you can take in the most amazing view of Chicago. They have these little clear boxes where you can look all around and down to the gorgeous city skyline.

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While catching our Uber to a Shake Shack run before our flight, we passed the Cultural Center which is a place David wanted to visit. So with 15 minutes to spare we hopped in to view the intricate architectural detail of the center.

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Then it was back to LA! Even though we only spent 48hours in Chicago I feel like we saw a lot of the city and squeezed in a lot of adventures. Can’t wait for another trip to this magical city.

IMG_1301‘Til next time Chicago!

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