Windy City

Well, I got back to Dallas last Monday night after five days in the Windy City. I turned 26 while I was gone. The trip was perfect, and I’m now closer to 30 than I am to 20, which is really weird to think about.

My best friend Jane moved to Chicago in August, so naturally my birthday gift from her was a plane ticket to spend a few days in her new city together. As we both say: best selfish gift ever. That’s what happens when you’d like to plan a trip, but you’ve used all your PTO: you bring your friends to you.


Sunrise over Chicago
My first view of Chicago after getting off the train at Block 37

My flight was at 5:15am, so I never actually went to bed, but I did sleep on the plane. For those who haven’t used it before, I tried The Parking Spot for the first time and I would highly recommend. You park in a gated lot near the airport, a shuttle picks you up right at your car, and gets you to the airport in just a few minutes. It actually ended up being cheaper than Ubering to and from the airport (#notsponsored).


City views
When your best friend leaves you an orientation note introducing you to her new place

I arrived in Chicago just before 8AM. After finding my way to the train, a train ride and a Lyft ride later, my carry-on and I finally made it to the apartment around 10:30. I was exhausted. Caroline, you are not 19 anymore. All-nighters are not a thing in adulthood – at least not something you can easily recover from.

Gorgeous architecture down by the river
City lights and night skies
Vino + a vegan home cooked meal

I changed into my sweats and spent a few hours working, relaxing and taking care of a few things before I headed out to explore. I made my way across the river and into bigger, more extravagant versions of the stores we have in Dallas. Jane was cooking dinner my first night there, so I popped into Whole Foods to grab a bottle of wine. Velvet Devil merlot. It’s the one bottle Jane, Patrick, and I all love. I opted to walk back to the apartment and enjoy the city views on my way. Jane cooked this incredible meatless (fake meat) pasta dish, zucchini pesto, and butternut squash. I don’t eat much meat, but I’ve never really tried out meat substitutes… it was really good! We spent the evening catching up on life and just enjoying being in the same place for a bit.



Oh look, it’s Buddy!

Friday, I woke up and grabbed some breakfast and a Nespresso brew and got a little work done. I wanted to dump any video down onto my computer before leaving, but eventually, I gave up and decided that the day must start. So I hopped in a car and headed to see my former boss, Danielle Moss. I met Conor, Buddy, and Tuck. And yes, Buddy really is everything you hope he’d be – so much personality packed into such a tiny body. And in case you were wondering, her place is just as incredible in person as it is on Instagram. It was great catching up with Danielle over coffee and seeing a little behind the scenes of an Everygirl photo shoot. Thanks again for having me, D!

Getting a little work done at the 3 Arts Building

After I left Danielle’s, I headed over to the 3 Arts Building to get a little work done at the cafe, where I wrote my last blog post. It was a 2-mile walk back to the apartment, but I thought I’d brave the 40º weather for the sake of exploring along the way. Chicago shopping is like an outdoor mall: the most beautiful storefronts along every sidewalk.

Give me all the beautiful old architecture
Fire escapes
I know #ihavethisthingwithceilings isn’t really a thing but…
Rag & Bone
#ihavethisthingwithfloors @anthropologie

I met Jane and Pat back at the apartment, and we popped into to Bottlefork (which I just found out has since been closed since I was there a week ago?!) for happy hour drinks before heading to Beatrix for dinner. If you’re into healthy eats or creative cocktails, you’ve gotta check out Beatrix. Potato salad deviled eggs, roasted cauliflower salad, wild mushroom risotto, and a turmeric-infused bourbon cocktail later, I was sold. Will definitely be going back during my next trip!

A quick note on friendships… Patrick, Jane, and I all have drastically different opinions about big topics of conversation: religion, politics, money – you know, all the things you’re not supposed to talk about? A lot of our dinner conversation revolved around these things – the election, politics, money, power, religion, human nature – and it was pleasant. This is a common theme in a lot of my relationships: we don’t shy away from talking about tough things, because we believe that’s how progress is made. There are things to be learned on both sides of any argument even if at the end of the day no one’s overall position is changed. Learning to have hard conversations well is part of what allows us to grow and our relationships to thrive. Total rabbit trail, but that’s a peek into our dinner conversation.


How gorgeous is this set up at Restoration Hardware?
So sophisticated
Basically my dream bathroom
When the stairwell looks more like a funhouse…

On Saturday I woke up with the most awful allergies. You literally couldn’t have counted how many times I sneezed.It was embarrassing actually. At some point Jane and I decided that her continually saying bless you was just obnoxious. We got up and had breakfast at the apartment before heading to the 3 Arts Building to explore Restoration Hardware. Everything is perfect and most all of it is way out of my budget haha. For reference, my almond milk chai + a coconut water from the previous day totaled $15. RH inspired conversations about how we envision our lives when we feel “more adult” or “more settled” while simultaneously realizing that most people never feel settled because life is always changing, and there will always be new obstacles.

Because our entire lives revolve around food, we looked for the closest, cutest place. On the way, we stumbled onto a little farmers market (so cute!) and eventually made our way into Q for brunch. Yep, just Q. I ordered way more food than I could eat, and left stuffed. We shopped most of the day. Jane got new snow boots and I got a new top for going out. Worn out by my sneezing, I took another allergy/cold/whatever pill as soon as we got home and took a powernap to make sure I’d be ready for dinner and hopefully a little going out.

When I visited Danielle, she and Conor recommended Bad Hunter, and I’m so glad they did. We got fried kale sprouts and parsnip chawanmushi (which is like a veggie and gravy-type situation). While we were at dinner, I got a message from one of our friends from college, Evan, asking what our plans were for the night. He was also in the city for his birthday and had seen that we were in town. So we spent the rest of the evening out with him catching up.


Sunday was my birthday, so I tried to strike the balance between a relaxed day and doing all the things. We took a slow morning before walking down the river to Hampton Social. We just sat and talked for hours, making up for the weekly girls nights we’ve missed for the last couple months. Two different local musicians really completed the atmosphere. It was just a lazy Sunday morning with all the good vibes of Coldplay, Jack Johnson, Frank Sinatra, and Ed Sheeran.

A necessary stop while in Chicago
Brunch drinks of choice: Montauk Point + Frose All Day
Sorry for the chipped polish

A girl sitting next to us asked about the drink Jane had ordered and we started talking. She moved to the city back in April and her sister was visiting for the weekend. Before Liz left, she offered to take our photo in front of the Rose All Day sign and let us know where she and her sister were headed next. It’s little situations like that that make you realize maybe making friends as an adult isn’t so bad after all.

Now I knew I’d have Monday to do a little more exploring by myself since Jane would have work. So I took the opportunity to also make a new friend and asked a stranger out to lunch the next day. What’s the worst that could happen?

Because you gotta get one of these

After we tabbed out, we headed to the Sky Deck, AKA Sears Tower AKA Willis Tower. We waited in the lines and did the touristy thing. But gosh… the VIEWS! Just unbelievable. There is just so much city, so much to take in. 103 stories up, we walked out on the glass floor. Now I’m not scared of heights. I actually love heights, and when I say that, I mean that I would actually have more fun if I could repel from the 103rd story.

Proof that Chicago is actually 50x bigger than Dallas.
Thankfully not scared of heights

103 stories up. Don’t fall.

For dinner, we had reservations at a small restaurant with a dining area the size of a small apartment. It’s called Blue Door Kitchen, and every detail is just so cute. We had a light dinner: deviled eggs, white bean soup and a glass of red. I left happy and full.

When we got home, my lunch date texted me to make plans. I let Landon* pick the place because who knows Chicago better than a local?



Monday, I got up and honestly felt too nervous to eat breakfast. I love travel, I love exploring, but it gives me so much anxiety. I just never feel settled on travel days until I’m seated on the plane. So I took a slow morning of making sure I had every last thing packed before getting ready to head to lunch. Jane’s cat Wednesday was adamant that I not leave. On the way to lunch, I had the most lovely Lyft driver who had some solid recommendations for my next trip. Thanks, Craig. He dropped me at Forbidden Root, this cool little microbrewery in West Town.

I wish I had taken photos, but that didn’t feel appropriate. I think we were at lunch for three hours? We listened to each other’s stories and bonded over similar values and opinions. Landon drove me back to the apartment so I could do any last minute packing and turn in my apartment keys before heading to catch the train.

After I got through airport security, I settled in at Starbucks and called my mom, excited to see her and Willow after I touched down at DFW. If you follow me on Instagram stories, you know that I almost cried when I had to say bye to Willow.



Friendship is so sweet. Experiences are everything. Both are definitely worth the investment. I couldn’t have asked for a better birthday than to spend a few days catching up with my best friend and exploring her new city!

When Jane and I booked my flight, I was thrilled that my flights were at such late/early times. I’d have 5 full days that way. After taking the trip, I realized that while that may technically true, my energy and anxiety levels don’t always allow for my experience to reflect that. Pulling an all nighter does not equal having a full first day. I think if I did it over, I’d travel at slightly more ideal times.

I actually really love a walkable city, and if I did live in Chicago, I really might not have a car. Larger cities have UberPool or Lyft ride sharing. It’s a great way to take cheap rides if you’re not traveling far or aren’t concerned about making a train or flight. I didn’t Uber as much as I thought I would, and rides didn’t cost as much as I expected.

When you’re in a city like Chicago, reservations are the way to go. You might even need to make them three weeks out because the city is constantly crawling with tourists.

Jane and Patrick have a Nespresso and it is life changing. I recently posted about Keurig on Instagram. I love how convenient it is, but I hadn’t ever had at-home access to barista quality coffee or espresso until staying with Jane and Pat. I’ve actually listed my Keurig on a local sale page, and you better believe I’ll have a Nespresso in my possession very soon.

I need to take it easy in the food and beverage department. I eat small portions, which is not what you get when you go out. Going out for two meals a day several days in a row is not something that agrees with my body no matter how healthy I’m eating.

Life favors the bold. That’s some solid advice from my Uncle Don. I took advantage of 5 seconds of courage, and now I have a new friend in Chicago.

*Name changed


Leave a Reply

Your email address will not be published. Required fields are marked *