As a Hawaii girl I love pretending to be a city girl for a little bit. The first big city I ever visited was NYC and since then I’ve been attracted to the exciting, fast-paced urban life.
Chicago has been at the top of my travel to do list for a while because it’s known to be the “cleaner NYC.”
My bestie Joleen and I decided last minute to do a quick girls trip to the Windy City— by the way if you didn’t know, Chicago didn’t get it’s nickname for actually being windy. Just learned that lol.
We arrived Sunday afternoon and left Wednesday afternoon so we had an evening, two full days, and a morning to stuff in as much fun and food of Chicago as possible.
A good amount of time on this trip was spent eating. I share a couple of my favorite Chicago eateries in this post, but if you want a full list of the best Chicago breakfast, lunch, dinner, and dessert spots be sure to check out this post here.
Here’s a list of 10 Chicago must do’s that you shouldn’t miss:
1. Power walk and power shop the Magnificent Mile
You can’t visit Chicago and not do any shopping. I mean there’s a three story Top Shop. That speaks for itself.
And shopping is my cardio 😉
2. Have a bite of Chicago’s famous deep dish pizza
Apparently there’s a huge rivalry between two deep dish spots, Lou Malnati’s and Giordano’s. Be the judge yourself and have a bite of both 😉
3. Get cocktails at the Signature Lounge on the 96th floor of the John Hancock Building
Happy hour is my second favorite hour. Can you guess the first? 🙂
4. Eat the prettiest gelato ever at Amorino Gelato
I’m known to have such a sweet tooth. This rose sculpted gelato was as delicious as it was pretty.
5. Play tourist with Wendella Boat Tour to learn about the architecture of the city of Chicago
Our tour guide mixed in Chicago’s history with the funniest dad jokes I loved it LOL.
6. Have an aesthetically pleasing lunch on a terrace with views of the city
When I posted a picture of our lunch spread I got SO many questions about where I was. I share this cute spot here.
7. Snap a pic 103 floors up at the Willis Tower Skydeck
I won’t lie I got pretty nervous when it was my turn to step out onto the glass but I had to do it for the gram.
8. Rooftop hop before dinner
There is no shortage of rooftop restaurants and bars in Chicago with views of the city. Pick a couple of places to hit up for drinks and tapas before heading to dinner.
9. Eat at RPM Italian & run into Guliana Rancic
Okay so you aren’t guaranteed to run into Guliana, but it’s worth a shot isn’t it?
This place is incredible think comforting Italian food in a trendy modern setting.
10. Visit Millennium Park & Take a selfie at the Bean
What’s better than eating donuts at the park?
The Bean is actually cooler than I thought it was. I wasn’t dying to see it initially because it seemed too touristy, but I’m so glad I did— it’s huge and the reflection of the skyline behind it was beautiful.
Being able to travel is such a blessing— there’s nothing I love more. I had a blast running around Chicago, seeing the beautiful architecture, tasting the best flavors, and spending quality girl time with my best friend.
It’s a cherry on top to share my adventures with you all!
Another location checked off my travel bucket list. 🙂 Where are you lusting to travel? Leave a comment below, I’d love to day dream together!
A Whole Lotta Love,