Travel Story: Chicago

Travel Story: Chicago

My bachelorette weekend in Chicago was a girls trip of a lifetime. It was filled with close friends, a ton of laughter, sparkly nails, bedazzled hair and shades, sightseeing, the best restaurants, snazzy nightlife and so much more. We had so much fun!!! Have y’all heard of the POV Cam? We used it all weekend thanks to my friend AGVG and it was a fun way to capture the weekend. And trust me, we definitely captured the weekend…. 1M iphone shots to prove it. Here are the highlights! 

FRIDAY SEPTEMBER 1ST 〰️ The Details …as I remember: 

12:30PM Arrived in Chicago. (For the first time since I was in middle school! Clearly it had been too long!) The bird’s eye view is stunning! 

1PM  Maggie greeted me with a mini champagne bottle @ the O’Hare airport. 

 

1:30PM Arrived at the Loews hotel in River North – Alex greeted me with another champagne toast (spoiled!!) We caught up, unpacked, went to the store to stock the hotel rooms, and I wrote notes to my girls in every room. 

4PM  We jumped up and down when everyone trickled in! 

4:30PM Drinks at the Loews rooftop bar – Streeterville Social. All fun and games until a bee took a bath in Taylor's drink. 

 

5:30PM Quick walk around hotel in River North 

6PM Surprise champagne and chocolates from India with In the Know Experiences! So sweet! 

They helped us get all of the rooms on the same floor. A pro tip! 

                                           

6pm – 7:30pm We all got ready and bounced around with drinks in hand. 

8PM Dinner at Shaw’s Crab House – An old school vibe with a great Oyster Shooter.

10PM Three Dots and a Dash Tiki Bar, *note: The infamous Banana Dolphin Daiquiri* made a great tiki table statement – late night flight peeps arrived! The whole group is here! We’re in Chicago!!

  

12AM Redhead Piano Bar to close out the night!

SATURDAY SEPTEMBER 2ND 

8:45pm – fun walk to hot yoga at Studio Three 

9:30am yoga – the best class!!! Highly recommend it if there's a studio near you! We had so much fun. We brought the energy to the class in the back left corner. I kept thinking how grateful I was that so many friends from different seasons of life were in the same room. 

 

11am – Brunch @ Goddess and The Baker 

1:30pm – Walk to the river! Everyone got dressed and ready and bedazzled. The stick-on gemstones were originally for the sunglasses I bought for everyone… ahem, *Shady Ladies* but my friends took it to the next level…. Just love’m! 2PM Architectural boat tour with Wendella Tours!!! Will need to go back to hear the details all over again...I had too much fun out on the water chatting with everyone. Matthew facetimed me for a moment during this which was sweet. 

   

4pm Pizzeria Portofino. This place was so fun. We’re literally in Italy!!! But we’re in Chicago!! Great pizza…and the burrata.. YUM. 

 

6pm – Bach shower! So fun!! 

 

8pm – dinner at EMA! Will never forget this hummus. 

 

10pm – As Jayne said, “on the weekend they call me: BUB CITY”– a country bar just felt right– Krista Lynn Meadow and her band performed and she fit right in with all of our main character sparkly outfits. Her tall, sparkly cowgirl boots gave her bonus points. 

  


SUNDAY SEPTEMBER 3RD 

9:45am Met up at Blue Bottle Coffee // FoxTrot Market // Museum of Ice cream – shops along Pioneer Court. Right around the corner from our hotel. 

Saw the Bean with part of the group and walked through Millennium Park to the Gardens, Lakefront Trail, and the Yacht Club along Lake Michigan. 

12:30PM Got dressed and had brunch at 12:30pm at Somerset in Gold Coast

2PM Shopped in Gold Coast – went in Vuori and Aritzia and while everyone was shopping around, I picked up a book on Willem de Kooning to read. 

3PM American Girl Store – We all got in our feels since this place brought back so many childhood memories.  

3:30PM Mall – Inspired by gorgeous dresses in Azeeza

Accessories shop - got Katherine Day a furry bunny key ring for old time's sake. She used to love that kind of random stuff. 

4:15PM Most beautiful walk along the lake back from Gold Coast. 

4:55PM Collapsed on a big couch in the hotel lobby after a day of walking and shopping. 

6:15PM ART IN THE PARK/ ART ON THE BEACH 

7:45PM We cancelled our reservations – we weren’t feeling a formal dinner and we ended up dining at….none other than Eataly

9PM on: Chill night with everyone in the hotel – giggling away. 


MONDAY SEPTEMBER 4TH 

8:30AM We packed up, then split up into small groups and explored the city this morning.  

10AM Then we met back up at our go-to spot along Pioneer Court (Fox Trot / Blue Bottle Coffee) 

10:30AM Bopped in the Krewe Sunglass Pop-Up Shop

11:30AM Found a random taco spot. 

1:30PM Walked to the West Loop (River North ✔️ Gold Coast ✔️ West Loop ✔️)

2:30PM Stopped in Levain bakery (Had to! 🍪)  

3:10PM Walked back to the River and wanted to end my time in Chicago with a classic “Chicago Dog” hotdog. Very important mission. Just when I was about to give up hope, a vendor stood out in the distance. A great ending to a Chicago love story. Laura Saur said it was a life lesson 🤣 “You’ll find what you desire when you stop looking for it.”

3:45PM Everyone who wasn’t loving their life with a Chicago dog picked up Foxtrot for the last time and we enjoyed lunch at the Loews hotel bar until we departed! 

4:30PM Uber to airport with Katherine Day until we got to the gates and had to part ways. Nothing better than a sister! She helped so much with the planning and making the weekend so special! 

7PM Flight home to Charleston :) I have to say, I would go back to Chicago in the summer every year. 


With each girls trip and wedding I'm in, I learn how to be a better friend. I felt so loved and showered. And I want to give all of that back in return to my friends who traveled from all over to be there over Labor Day weekend. There were truly 12 MAIN CHARACTERS on this trip. We had the best time. A big shout out to my besties for making it so sweet AND SO FUN:) I’m becoming a pro at this ole’ celebrating life’s occasions thing! Invite me to your next party! Ha! I’m soaking up our special season and eager to be a party of my friends’ moments when it’s their wedding season too! Keep celebrating! 〰️ MK

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