Pro Tip: Take The Girls Trip!

A love letter to friendship (and Chicago)

I settled into my friend’s couch in downtown Chicago. It was around 9pm and we were both in pjs, a box of Captain Crunch between us. She had made us both chicken and pesto pasta for dinner, and refused to let me help.

“It’s so easy!” she insisted. “There’s nothing for you to do!”

We both ate with our feet curled under us, lounging on her sofa, yapping about anything and everything under the sun. I had politely asked if she had a little something sweet for dessert (I live for something sweet) and if not no worries, I could pick up my own groceries tomorrow. She playfully pulled out the box of cereal and both of our eyes lit up.

“That’s IT,” I said.

We took turns scooping handfuls of sugary cereal, and continued our chat til I couldn’t keep my eyes open. I remember thinking as I dozed off that this is what my stupid little life is about. This is why I bought the plane ticket—to chat til midnight over a box of cereal while the L train rumbled outside my friend’s cozy Chicago apartment. Bliss.

Awa and I! 😍

My friend Awa and I met performing in a show together. We played sisters and sat next to each other in the dressing room. I’d sum up our relationship as just being…totally ridiculous. Like we are so dumb, in the best way. No one makes me laugh like Awa. I played a beggar woman in the show we were in and every time I put on my costume, she would sing the Game of Thrones theme in a funny voice. We sing nonsense songs. We’d get in trouble backstage for laughing too much. But we also have deep, profound convos about life and love and all the things. It’s so cutie having a friend like Awa!

Awa is on tour with a show now, and even though it ran in DC, I had an idea that I should see the show in Chicago, to take a trip and make a memory out of it. I called her out of the blue to tell her and she said “YES. DONE!” and that was it. I’m fortunate enough to have a job that I can take on the go, and we both chatted about having time in a new city to just be. We didn’t make any major plans because it was a working trip for both of us, but also because we didn’t need to. We literally just wanted to vibe, and that’s exactly what we did.

We ran errands at Target. We walked on the treadmill at her apartment gym. We treated ourselves to sushi. I worked while she performed, and of course, saw her show while I was in town. It was just a bunch of little everyday joys—good food, great convos, and inside jokes formed in real time (I’ll spare you, hehe)

Awa is a star and was performing in Jaja's African Hair Braiding at Chicago Shakespeare Theatre hehe

If you’ve read my previous posts from this year, you know I’m prioritizing friendships in 2025. Perhaps it’s just because I work from home and could very easily stay cooped up in my house all day, but I really want to make an effort to love and support my friends this year. I want to be the friend who shows up. I want to be the friend who celebrates her friends' successes. I want to be the friend who calls you up just to say hi and check in. It’s so easy to get caught up in work and life and responsibilities that friendship gets tossed to the back burner. But your relationships are so worthy of being invested in. 

I heard somewhere that you’ll never regret spending money on quality time with loved ones. Whether that’s a trip, a dinner out, a coffee date, or preparing a meal at home—it’s always money well spent. And I totally agree. 

So take this as your sign to book the flight. To text your bestie. To make plans. Life is too short! And who doesn’t want cutie midnight convos on the couch with Captain Crunch? 🤍

A Mini Guide On Planning A Girls Trip To Chicago

• Southwest Wanna Get Away fares are where it’s AT. I was able to score an incredibly cheap flight and was honestly inspired to look for more flights because of how reasonable these fares are. Southwest also makes it super easy to make changes. I was actually scheduled to travel a week earlier, but Awa got sick and it was also like…5 degrees. Switching flights took two seconds and cost nothing. A dream!

• Keep it casual. Yes, this is coming from someone who just made custom stickers for an at-home coffee house (lol) but there was so much ease during this trip because we were just vibing. Of course, trips with more people will probably take a bit more planning, but prioritizing quality time was the most important thing.

• The Ralph Lauren in Chicago is four (wait, five!?) levels and is completely stunning. I spent an afternoon working at Ralph’s Coffee (duh) then spent like, 45 minutes walking through the enormous store. The way it’s curated had me basically crying, and I’m extra so you may not feel that way, but wow. It’s so much bigger than the two in the DC area. 

• The Coach store on N Michigan Ave is full of cuties. I popped in as I was walking home just because and I think I made like, 3 friends instantly. Everyone there was so nice and the store is beautiful!

Things I Wish I Did But Didn’t Have Time For

• The espresso martini flight at Starbucks Reserve: I was in Seattle last year and didn’t make it to the Starbucks Reserve there, but I knew I had to walk through the one in Chicago. It’s huge! If I had more time, I would’ve made a reservation for some coffee cocktails at the bar, specifically their espresso martini flight. 

• Dinner at Girl and the Goat: If I had planned ahead of time, I would have made dinner reservations at Top Chef’s Stephanie Izard’s restaurant, Girl and the Goat. I was there during restaurant week too, gah! I totally would have done the restaurant week prix fixe, but they were booked til 9:30pm on the one night I was free, which is simply too late for me and my grandma self. 

• The Art Institute of Chicago: It would have been nice to take a peek at A Sunday on La Grande Jatte and American Gothic, but an art museum requires a totally free afternoon with time to stroll imo, which we didn’t quite have enough of. I’m also completely spoiled with free museums in DC, and a ticket for the Art Institute is $32, so a part of me felt like it was ok I missed it? I need to take advantage of what I have!

I hope this little post inspires you to take the trip. I hope you say yes to time together with your besties. And I hope you never forget that friendships are worth every ounce of effort. I’d love to hear about your own girl's trips, or even a small and meaningful thing you’ve done for a friend recently, or vice versa. It’s almost Galentine’s after all! 

Cheers to the girls🥂✨

xx, Kristen

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And if you want to hang on the daily, be sure to follow me on Instagram! This week I shared low cost ways to feel fancy, I confessed to being an aisle seat girlie and you can see Awa and I enjoy our sushi night 🍣💕