Documenting the life and times of a dreamer on her gap year. 

A Windy City Welcome

A Windy City Welcome

This past weekend, I had the opportunity to return to one of my favorite cities ever -- Chicago! Here’s a post chronicling what I ate, wore, and did over three action-packed days.

Even the most hardcore of sports geeks (i.e., my godfather, a retired senior copy editor/assistant sports editor for the Dallas Morning News) will probably find this a bit strange, but this past weekend my dad and I headed up to Chicago with one event in mind: The National Hockey League Draft. Yep, pretty strange -- my aforementioned Uncle Bo commented that he’s never known anyone to attend a sports draft for fun instead of work! But let me tell you, the experience way surpassed my expectations.

Of course, some of that came from the fact that it was in Chicago, of all places. My paternal grandfather grew up in the bustling Greektown, so my dad has been a Chicago lover from an early age. There’s just something intensely refreshing about the Windy City that inspires me beyond words, so it’s no surprise to me that my first blog post is about my experiences there.


We arrived in Chicago at about 1 p.m., and I’m sad but not all that surprised to say the main thing on my mind was food. Our Starbucks from three and a half hours earlier seemed like it had been in a different century, so by the time our taxi driver finished the long, traffic-heavy drive from Midway to downtown, I was pretty much ravenous. Unfortunately, the majority of the restaurants close to our hotel were only breakfast places and closed at 3, so once we had checked in and left our bags with the bellhop until our room was ready, we basically would have had half an hour to eat. We’re heathens and need way more time than that, so we just started walking toward Navy Pier. The walk is about three quarters of a mile, and we got all the way there before turning back around and going to the Whole Foods across the street from our hotel. Ah, Whole Foods. You never let us down (please Jeff Bezos...don’t ruin it). A curry wrap and some plantain chips later, I was totally revitalized and ready to head to the draft.

I wore what must be a limited edition Rags of Honor tank top (I can't find a link anywhere!), a grey shirt emblazoned with the secondary Blackhawks logo, along with some Rewash army green joggers and my trusty Adidas sneakers.


I also wrapped my Dallas Stars jersey around my waist when it was too hot to wear, a look I repeated with my Blackhawks jersey on Saturday and that I’ll definitely be incorporating into my “she likes sports, but she also owns real clothes” looks in the future.

After the draft, we considered going to Giordano’s (a Chicago must!) but the wait was an hour, and it was already 10 p.m. by the time we arrived at Navy Pier. Thus, we headed over to America’s Dog, a hot dog place in their fast food court. I had my first-ever Chicago dog (sans sport peppers), and just like every other thing I experienced in Chicago, it definitely made me fall a little more in love with the city. I mean, I even liked the relish. Who am I?

Then, we headed back to the hotel, ready for a full Saturday of Chicago adventures.


We woke up fairly early on Saturday to take advantage of the complimentary hotel breakfast and be on our way to the later rounds of the draft, which started at 9 a.m. I wore a grey Blackhawks t-shirt and my all-time favorite leggings, cropped black ones from Tangerine (where are you, perfect leggings? I can't find a link for them!!), with my Adidas sneakers and Blackhawks jersey. To tie together the color scheme I added a navy-and-red Bring Hockey Back snapback with “Legs Feed the Wolf” emblazoned on the front. Some fellow fans asked about where I got it, and I was so happy to give one of my favorite hockey brands a shoutout -- the unique hat definitely made me stand out!

The Fan Fest, an outdoors event with activities, food, and photo ops was filled to the brim with friendly fans, and it was seriously a joy to be there. The highlight was obviously my first meeting with the Stanley Cup...my awkward hand placement is definitely because my hands were shaking with excitement!!

We’d basically powered through six hours of fun in the sun on the Embassy Suites breakfast and a couple of Vitamin Waters, so a snack back at the hotel was definitely in order.  What better way to celebrate the end of an athletic endeavor like the NHL Draft than some PopChips and an ice cream sandwich? That’s definitely a sign of traveling with your dad.

I showered and napped while my dad did some work, and then it was finally time to get our Giordano’s. Thank GOODNESS. Off to Navy Pier we went. I wore a floral romper from Forever 21 in green and yellow, and my blue Steve Madden Brando sandals. An easy-breezy outfit perfect for a warmer summer night, and best of all, super convenient for a weekend getaway as it’s an entire outfit in just one packable piece!


The Chicago Pride parade had been going on earlier that day, so the Pier was full of beautiful rainbow decorations celebrating the vibrant LGBT+ community of Chicago.

We got on the waiting list for Giordano’s, pre-ordered our pizza (Super Veggie, yum), and kept walking around the Pier.

Finally, it was time to eat. We each started with a chopped salad, which was maybe my favorite new find of the weekend. Any salad with pasta that is still somehow healthy is a friend of mine. And of course….the star of the show….the pizza (apparently I was too hungry to properly focus!).

We were way too full for dessert, so we just walked around the pier for a little while. We got super lucky, as we stumbled upon a fireworks display! Every Wednesday and Saturday night throughout the summer, fireworks go off above Navy Pier, and it was a treat to see...fireworks equate to such pure joy for me, as I usually only get to see them on Fourth of July and the Happiest Place on Earth!! We just seriously had such great luck in Chicago. What a perfect end to a great day. 


Sadly, our trip came to an end Sunday morning. We packed up and stopped by Yolk for a…light breakfast.

Apparently there are several locations of this breakfast restaurant in the DFW area. Lucky lucky us!! Though the iced mocha wasn’t my favorite, the breakfast more than made up for that. I went with one each of the Nutty Monkey Cakes and the Banana-Blue Crunch Cakes (the latter definitely gives the Giordano’s salad a run for its money on my favorite food discovery this weekend!). I topped that off with a giant side of the applewood smoked ham. It seriously felt like Christmas morning.

I think I wore the perfect outfit, not only for traveling but for concealing my gigantic breakfast! I wore a Forever 21 bodysuit with an open back, my Free Press wide-legged black pants (they’ve become a staple in my wardrobe) and the Adidas’ made another appearance.

So comfortable, this outfit basically felt like pajamas, which I proved by sleeping through the entire flight!

Thus ended my trip. Short and sweet, but totally action-packed and probably my favorite trip so far this year. Thank you, Chicago!!

Totally TOMs: Warehouse Sale Haul!!

Totally TOMs: Warehouse Sale Haul!!