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Chicago: the Great American City

“I adore Chicago. It is the pulse of America.”

My cousin, Kelly, lives in Dallas. I live in Philadelphia. This past Labor Day, we decided to meet up in the middle and spend the weekend in Chicago and ooooohhhh what a weekend it was!

Chicago swept us up pretty much immediately. We took the subway from O’Hare to Clark & Lake Streets, and upon emergence from underground, we could already feel the buzz of the city. We passed the famous Chicago Theater, crossed underneath the El train and eyed up a world renowned deep dish pizza place all on our walk to the hotel. There were people everywhere, but the streets somehow felt tame and safe. And everything was so clean! Does anyone else agree? Isn’t downtown Chicago so clean? (Or is my Philly showing?)

We stayed in the Hyatt on Upper Wacker Street and we were SO pleased by the location. For us first-timers, it was perfect – close to all the touristy hot spots, bars, restaurants, Lake Michigan and anywhere else we needed to go was only a few dollars away via taxi. Staying in such a central location made the weekend so easy and relaxing. Plus, we were on the 33rd floor which gave us an AMAZEFEST view of the river and skyscrapers. It was enchanting at night and beautiful to wake up to in the morning.

(Bonus: One Direction was allegedly staying in the hotel across the street from us for their weekend concerts. I was obviously was on 1D-watch the entire time.)

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Going into the weekend, we had each come up with a few ideas for things we wanted to see or do, restaurants we wanted to try, stuff to do at night. I don’t really like have an itinerary to stick to when seeing a new place – this was a fun girls trip, not work. Why have a plan? Having a strict schedule always makes me feel like I’m not letting things just happen. (Example: my friend and I went to Prague in May, and our motto for the trip was “no rush!” We had zero expectations of the city upon arriving and we ended up wandering the streets in absolute awe for the days we were there. Prague was pure magic and we experienced it so intimately because we had zero idea of what we wanted to do.)

HOWEVER we did have a few things we definitely knew wanted to check out at some point over the weekend, including: the Skydeck of the Willis (formerly Sears) Tower, deep dish pizza and a Second City comedy show. We accomplished all three and none of them disappointed! Here are a few pictures from the trip:

10599639_2339848903144_86914528339581438_nOur number one priority after checking into the hotel was eating food. We were staying just a few blocks from the famous Giordano’s restaurant, where we indulged in pitchers of Chicago-brewed IPAs and deep dish pizza. It was the perfect start to my inaugural trip to the Midwest.

IMG_0780IMG_0777We ended up taking lots of photos posing with our food. It was kind of weird. On our first morning/afternoon in Chicago after a ~wild~ night out (did you know a lot of bars stay open until 4 am in this city?!?), we got brunch at Eggy’s Diner. The food was outstanding – I got Nutella french toast (I KNOW, RIGHT?) with bananas, a side of bacon and a fresh mango smoothie. Plus, the manager was the nicest guy we met all weekend! He chatted with us throughout our entire meal and invited us to come to his stand up comedy show that night. We went, and it was hilar.

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IMG_0837One of our favorite, unexpected parts of the trip was this architectural boat tour we took along the Chicago River. Our tour guide was incredibly funny and informative, and we learned so much about Chicago’s history! Pics taken from the river:

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IMG_0889 IMG_0891That night was our comedy night: first we started at The Comedy Bar with our new friend from Eggy’s, then made our way to the epic Second City show.

10610816_2339859583411_9035678106867363010_nI could go on and on about all of the wonderful things we saw and experienced in Chicago. The two last big tourist attractions we went to were the Skydeck at the Willis/Sears Tower and Navy Pier. We were so excited to go up to the top of the Willis/Sears Tower, but when we actually got up there (103 stories up!) we were surprised by how uneasy we were! It really takes a lot of courage to stand out on those glass floor boxes:

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It was a phenomenal first trip to the Windy City, but I know I will be back sooner than later. Chicago and I really vibed. We really connected, and I don’t ignore feelings like that. I’ll be back.

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8 Comments

  • Reply skyward eyes

    […] skyline as seen from the tip of Navy Pier! Kelly & I spent our last afternoon of our Labor Day weekend in the city having lunch by Lake […]

    September 22, 2014 at 2:50 pm
  • Reply Pre-commitment bucket list | skyward eyes

    […] high school trip to Greece, partially-skinny-dipped in Lake Michigan with some French bros at 4am (love you, Chicago!), and even partook in a few unmentionables from a semester spent gallivanting across Europe with a […]

    October 6, 2014 at 6:32 pm
  • Reply MissLilly

    Really nice! Want to go too

    October 13, 2014 at 3:30 am
  • Reply September, according to Instagram | skyward eyes

    […] has been a roller coaster of a month. There were a lot of high points, like welcoming the month in Chicago with my cousin whom I rarely see, and there were some lows. I’ve been taking the past few weeks to […]

    October 27, 2014 at 12:03 pm
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    January 19, 2015 at 6:47 pm
  • Reply The great state of Texas | skyward eyes

    […] cousin Kelly (we traveled to Chicago together in September and she visited us in Philly in November!) came over to her parents’ house with her boyfriend […]

    January 31, 2015 at 3:47 pm
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