A FUN TRIP TO CHICAGO

TRAVEL
Written By Jolene Wright

This was our first time on an airplane in over 2 years and it honestly felt so good to be in an airport again! I definitely caught the travel bug and I’m so happy to start traveling again! Traveling is definitely one of Ryan and my favorite things to do together!

We just went to Chicago for the first time and I truly fell in love with this city! The architecture is stunning and we ate at some of the most amazing restaurants! If you’re thinking of going and you love a city vibe that’s full of life, I would 100% say go here! It felt like a mini New York City and I love that vibe so much! We went for 4 days and I could have stayed another night! The weather was absolutely perfect, so I would definitely recommend going in mid to late September! If you want a little cooler and even more fall type weather, the first week of October would be beautiful too!

Here’s a little travel guide if you need some help planning your next trip!

D A Y O N E —

We got to our hotel around 5pm and we didn’t have a lot of time, so we relaxed a little bit in our room and unpacked before getting ready for our dinner reservation at True Food in River North. I know what you’re thinking, why is she going to True Food in Chicago when she can literally go there anytime, but I knew it was close to our hotel and we would be starving — there wasn’t a ton of vegan restaurants to choose from, so this was the perfect spot to go our first night! We were able to walk to dinner and get our first views of the city by walking through the lit up streets! To finish off the night, we went to Z Bar, which is located inside The Peninsula Chicago. The interiors are stunning and the city views are even better! It was literally the perfect spot to start our trip!

- outfit links - (I didn’t get any outfit photos this night, but you can see it in my most recent YouTube video!)

Green flannel - https://us.princesspolly.com/products/ken-checkered-shirt-green | https://bit.ly/3lbVRd6 (similar)

Black crop top - https://bit.ly/3ldLRAj (similar)

Black trousers - https://us.princesspolly.com/products/archer-pants-black | https://bit.ly/3Acukg4 (similar)

Fila Sneakers - https://bit.ly/2UR1tyS

D A Y T W O —

We started our day by going to breakfast walking distance from our hotel. If you can see a theme, I absolutely love being able to walk everywhere, so we really loved staying in the Magnificent Mile area where we were pretty central to everything! This was my first trip having to shoot content, so I made it a priority to wake up early each day and get fully ready to take photos before or after breakfast and get it out of the way early to enjoy the rest of the day and be present! There truly are so many beautiful spots on almost every corner! The architecture was my favorite thing about Chicago! We were lucky to find a perfect spot right next to where we had breakfast at Kanela Breakfast Club next to Navy Pier. After breakfast, we walked around River North and Millennium Park. I truly love just walking around in a new city and taking it all in! Millennium Park was beautiful with so much greenery right in the middle of the city! I loved seeing all the people outside enjoying the day just walking around or sitting in the grass having picnics! Then we went to The Art Institute of Chicago. One of my favorite things to do when we go on a trip to a new city is to go to the art museum there and this one did not disappoint! I literally was in heaven in there and could have stayed the whole day! We went back to our hotel and got ready for an early dinner at 3 Arts Club Cafe inside Restoration Hardware located in the Gold Coast. YOU GUYS, when I say I’m obsessed, I’m like OBSESSEDDDD! First off, the buildings in the Gold Coast give me all the heart eyes! Once again, it’s the architecture for meee! And then you walk into RH and everything is unbelievably STUNNINGGG (obviously) — I was ready to move in! Our server, the interiors, the ambience, the food, the vibes were so high there! This was by far our favorite night! The dinner was UNREAL and then we spent hours walking through the six levels of RH! Everything was so chic, luxurious, and dreamy about this entire night! If you come to Chicago, you HAVE to make a reservation for dinner at 3 Arts Club!

D A Y T H R E E —

We went to breakfast at Goddess and the Baker in River North! It was so cute inside, had amazing energy, and the food + the coffee was so good! It was in a perfect location, just a short walk to The Wrigley Building where we went to take photos along the Riverwalk before going on the architecture boat tour! We absolutely loved being able to be on a boat on the river for an hour and a half seeing all the beautiful buildings and enjoying the sunshine! We had the most amazing weather while we were in Chicago! I would highly recommend doing this boat tour if you love architecture and historical buildings! After the boat tour, we went up to the London House rooftop bar to take in even more stunning city views and these did not disappoint! After we had a drink on the rooftop, we went down and walked along the river and stopped at City Winery. It was so nice being outside overlooking the water, seeing all the people walking by, and having those peaceful moments. For dinner, we went to Sunda Chicago in River North. The interior was so moody + vibey and the food was so good! After dinner, we walked to Andy’s Jazz Club. It was SO fun and we had the best time! This was my first time going to a jazz bar and I loved every second! I definitely want to find more of them because Ryan and I LOVE jazz music!

D A Y F O U R —

We loved Goddess and the Baker so much we had to go back for our last day! After breakfast, we shot the last bit of content and went back to our hotel to pack our bags. We went to a late brunch at Althea located in Saks Fifth Avenue and the food was honestly UNREAL! It was the most amazing plant-based culinary experience with more gorgeous city views! While we were at brunch, we bought last minute tickets to the Cubs game at Wrigley Field because this was the one thing Ryan really wanted to do, so I had to take him to a game! I’m really glad we got to experience it and it was such a fun way to end our trip! We definitely weren’t ready to leave after four days and would have loved to stay one more night! We can’t wait to plan another trip back!

- outfit links -

Black oversized blazer - https://bit.ly/2Xvsj0H

White tank top - https://us.princesspolly.com/products/kayla-crop-top | https://bit.ly/3lkzhiN (similar)

Levi's denim shorts - https://bit.ly/3DhY3Gq

Fila sneakers - https://bit.ly/3aaYPbA

Black NY baseball cap - https://bit.ly/3Cmxijw


— Princess Polly 20% discount code: JOLENE


I hope you enjoyed getting a glimpse into our trip and that it brought you some inspiration for your next trip to the city! You can also watch our Chicago Vlog on YouTube here!

Thank you so much for stopping by my corner of the internet! Xx

Jolene Wright
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