Travel Photography + How I Documented Chicago

One of the best things I did this month was take a weekend off from everything (i.e. wedding planning) and head to Chicago for some fun with Charles!

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I wanted that memory. That memory of us dating and heading away for a weekend to do something different. That is how the idea of a weekend in Chicago happened. 

Charles mentioned in the past that Chicago was a city he wanted to visit one day. After Christmas, I thought it would be fun to surprise him with a weekend trip away. I began researching cities and found a direct flight from New Orleans to Chicago within budget. With those criteria checked, I was excited to start planning a trip to Chicago. 

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A surprise. 

I am terrible at keeping secrets. Especially when a trip is involved. I get excited, and then I tell everyone I see. And like other surprises in the past, this trip was hardly a secret for long. Three days after researching (and not officially booking anything), I spilled the beans to my mom and my best friend and Charles’ boss and the lady at the grocery store bagging my groceries. Because, you know, I was excited. Shortly after, Charles knew what I was planning and was completely up for a weekend in Chicago.

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Each vacation is different. How I photograph and what I chose to photograph change depending on what I want my vacation to be. 

I photograph quite a bit. Some trips I want brake from my DSLR and shooting in general. Other trips I look for new scenery to inspire me. The goal of this trip was somewhere in between. I was excited to photograph the city, but the cold kept me from pulling out my camera as often as I would have liked.

We booked tickets for Hamilton a few weeks before we left. Other than those tickets, our itinerary was free. A week before we flew out, I realized I booked flights for the weekend Chicago was celebrating St. Patrick’s Day. So, my goal that weekend was to snap some photographs of the river being dyed green and a few shots of the city with St. Patrick’s Day themes.

Luckily, our hotel room faced the river, which meant we watched from the warmth of our room (rather than the freezing cold) as the river went from blue to green in a matter of minutes. I snapped some shots from our hotel window using the height of our hotel room to create a unique view and the window panes to frame and create interest in the photographs.

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Depending on weather conditions and daily activities, I photographed with my DSLR as often as possible. If weather and activities did not allow, I used my iPhone as backup. 

Saturday was beautiful (and cold). The hardest part of this trip was photographing with my DSLR and cold hands. I wore a pair of gloves with mittens on top each day – I can admit that I am a wimp in cold weather and that is one of the reasons why I love the south and our warm temperatures. I had to really want a particular shot to battle the cold, gloves, and photograph with my DSLR. When I did use my camera, I photographed some beautiful street shots as we walked along Michigan Avenue.

Since we purchased tickets to Hamilton, we walked to the PrivateBank Theater Saturday afternoon to see where we would be going later that night. I am glad we walked to the theater in daylight because I photographed afternoon shots of us just in case the darkness and crowds were packed later that night.

On Sunday we did the tourist thing and headed to Willis Tower to see views of the city.

Monday morning when we woke, the city was turning white from snow fall. We grabbed breakfast next door to our hotel. I did not want to walk far in the cold and snow. Did I mention I am from the south and we do not get cold weather like that?! I was out of my element and covered in many many many layers.

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Itinerary Ideas: A Few Places We Ate + Visited

  • Friday night seafood for Lent at Shaw’s Crab House
  • Ordered four different small plates at The Purple Pig  – our waitress recommended some delicious dishes!
  • Chicago style pizza at Giordano’s – not the way I expected a deep dish to be, and very good!
  • Walked along Michigan Avenue
  • PrivateBank Theater for Hamilton – my favorite part of the trip – I loved Hamilton!
  • St. Peter’s Catholic Church for Sunday Mass
  • Willis Tower for views of the city (very touristy)

XOXO – Ashley “The Future Mrs. Hooker”

One last thought… I am so glad we did this trip. I needed the break and the rest. And, I love exploring a new city with Charles. It was great weekend to get away! 

2 thoughts on “Travel Photography + How I Documented Chicago

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