Travel Diary: Chicago

August 7, 2015

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Photographer - Olivia Yuen/Cecilia Yuen
Photo Editing - Olivia Yuen

Happy Friday Everyone! From the bombardment of my Instagram photos, it is no secret that I have jet setted to Chicago/Chi-Town/Windy City a few weeks ago. Traditionally, I go home every year to celebrate my birthday with family and friends. Since me and my sister's birthday are super close, we decided to turn the tables this year and celebrate our birthday's in the Windy City with my brother and his girlfriend. I have not seen many cities in my lifetime yet, but Chicago is by far my favorite city and the most memorable trip I have been on. It took my breath away with their stunning skyline and architecture. It is a well-developed city worth seeing. As I was packing for this trip, I kept in mind where I would be going and what I would be doing each day. So I kept it easy with one pieces such as rompers and dresses with jackets. Continue to read below as I take you through my travels and adventures through each outfit.

Day 1
Started off the day by bonding with my siblings and best friend over a delicious brunch place called Yolk! We walked around the city and I was awed and captivated by the extremely tall buildings. Later, we went to Montrose beach to soak up the sun with stand up paddle boarding and kayaking. We then made our way back into the city for the Wendella Boat architecture tour near the hour of the sunset which I highly recommend! Seeing the sunset and light glimmer on the buildings was something I will never forget. Special thanks to my brother and his girlfriend, we ended the night with a birthday dinner for my sister and I at Girl and the Goat. I kept the look for this day comfortable and casual since it was more of a relaxing day.

Day 2
A Chicago trip would not be complete without going to the two biggest tour attractions the Skydeck Chicago at the Willis Tower and Cloud Gate aka “The Bean”. So that’s what we did! We started off the day with brunch and continued our day by walking over to the Willis Tower. We waited for roughly 1 1/2 to get 103 floors up to the Skydeck. The 360 view of Chicago was well worth the wait. We took in the view of the city for a while and continued our way to the glass box. Standing 103 floors high in a glass box with the view of Chi-Town was priceless and breathtaking. Snapped a couple of pictures and made our way take a little break and refresh our palettes at the Willis Tower Starbucks. After, we walked over to the Millennium  Park, the home of the Bean! Goal sightseeing accomplished! Since the Willis Tower and The Bean are such iconic tourist sites in Chicago, it inspired me to make a statement in my outfit. I kept the outfit chic with a red romper and layered it with a leather jacket and statement necklace.

Day 3
Sister’s birthday! Took a trip by Lake Michigan to visit some sea life at the indoor Shedd Aquarium. I was surprised to see a leafy sea dragon, blue starfish and blue lobster for the first time. After the aquarium, we walked over to the Adler Planetarium. Along the way, there was a beautiful view of the skyline meeting the green grass and sparkling blue waters of Lake Michigan. Walked around the Adler Planetarium and watched a show. Completed the night with the famous Chi-Town deep dish pizza and a movie. Since it was an easy day, I kept my outfit simple with a chambray dress and a yellow bag for a pop of color.

Day 4
Walked miles through the city to the Navy Pier to ride the ferris wheel and found that there was an indoor rainforest! We walked south to the famous Buckingham fountain then made our way to Chinatown for dinner and boba. Inspired by the vibes of the Navy Pier, I went with a navy blue striped dress with cord detailing at the neck and red accessories.

Day 5
For the last day in Chi-Town, we took a trip to visit the FREE Lincoln Park Zoo. Note that this is one out of the three free zoos in the states! We took our time to walk around and enjoy the zoo. After, we walked over to the heart of the Lincoln Park where there was the Lincoln Park Conservatory for a tropical experience full of exotic plants and ferns.  Continuing to explore Lincoln Park, we were happy to discover a nature boardwalk where we found a dome that looked like a uniquely, sculpted bee hive. Took some Instagram photos and just soaked up all the nature and urban oasis around us. We walked about 2 miles to dinner and that’s when I fell in love with the vibe of the city.

Thank you so much for reading my travels and I hope I inspired you to visit Chicago someday! Have a great weekend and I will talk to you soon.

Fun fact: Chicago is not called the windy city because of  the wind. The term is used metaphorically to make out that Chicagoans were braggarts.

Outfit 1

Top - Madewell
Skirt - Zara
Necklace - Urban Outfitters
Necklace - Topshop
Bag - Zara
Shoes - Sam Edelman

Outfit 2

Jacket - Zara
Romper - Zara
Necklace - Baublerbar
Bag - Zara
Shoes - Zara

Outfit 3

Dress Asos
Sunglasses - Topshop
Bag - Zara
Shoes - Zara

Outfit 4

Dress - Zara
Sunglasses - Topshop
Bracelet - Zara
Bag - Zara
Shoes - Sam Edelman

Outfit 5

Romper - Asos
Sunglasses - Topshop
Bag - Zara
Shoes - Zara



  1. I love all your outfit! Happy belated birthday, looks like you had a wonderful time. Your so stylish!

  2. Such wonderful looks! Very lovely!

  3. It sounds like you had an amazing time! I'd love to visit Chicago someday- it looks very lovely from your photos. Your outfits for the trip were really lovely too- my favorite is the red dress + black jacket combo :)