Somehow my family picked the all-time best weekend to be in Chicago. No joke, it was like all the stars aligned and the Windy City’s gods smiled down upon us. Our reason for going to Chicago was so that my sister could see Hamilton, in celebration of her 18th birthday. We had no idea we’d be in Chicago the same weekend as the cubbies’ historic ascent to the World Series (!!!) Like what?! It made the city feel a little more electric and Chicago really goes all out with their decorations–so the combo of halloween decs and historic statues donning cub-wear really pulled on my heart strings. Plus, Kyle Hendricks, a pitcher from the Cubs went to my undergrad at the same time as me! & On top of all that, the band Joe Keery is in (aka Steve Harrington from Stranger Things) was playing a free double-header. I’m by no means a Chicago expert, but I really love that city, and I feel like I left a piece of myself there. I don’t think it’s a coincidence that two of my absolute best friends from college are from the Chicago-area. So read on for some of my suggestions and please share your own, because I know I’ll be back soon.

Whenever I travel somewhere, I tend to get a little distracted by food, drink, and live music. So traveling with my family is a great excuse to hit up some of the kitschy, touristy places too and man, did we hit them up. We bought the CityPass which gave us “VIP” access to the Field Museum, The Shedd Aquarium, the Art Institute, 360 Chicago (fka the John Hancock Observatory) and Willis Tower (aka Sears Tower). The pass costs about $100 bucks, but for all  you get I definitely feel like its worth the price, especially if you have a few days in the city and it’s your first time.  But if I had to narrow it down, I would definitely choose 360 Chicago over Willis Tower (less crowds, better views imo), and the museums. The Ferris Wheel isn’t included in the City Pass and I would probably skip it because the views are way more insane from 360 Chicago.

Continuing the tourist theme, I definitely recommend Portillo’s (the one on Ontario Street) for a an Italian Beef sandwich or Chicago-style hotdog.

If you are like us and seeing Hamilton in Chicago, I 100% recommend going to Revival Food Hall before the show. It closes at 7pm, which works out fine since the show starts at 7:30 and its literally a 3 minute walk from the theater. If you are with a big group it is great, because people can choose whatever sort of food they want, since it is basically an upscale version of a mall food court; it even has a great cocktail bar. I recommend the poke bowls from Aloha and acai bowls from Graze. If you are feeling a little more adventurous, try a sandwich from Danke which uses interesting cuts of meat..like blood pate.

The next day we started the day off with coffee and donuts from Stan’s Donuts. They are pricey, but really good. Our favorites were the cookie butter and pistachio ones–do the cookie butter one for sure.

Sorry to keep going on about food, but I just have two more restaurants to cover. I was super looking forward to both of them. First up was Girl and the Goat, it’s been around for awhile and has spawned a few sister restaurants, but somehow still remains a hard res (I made mine months before our trip) and was bumping even when we were there at 5:15 pm on a Friday. It’s known for its interesting takes on slightly out-of-the-box meats, but I thought where it really shined was its bread, oysters, and veg dishes. So for sure, get the chickpea fritters, whatever breads/butter they are offering and the oyster specials of the day.  I was not a fan of the pig face (too fatty) or the octopus (too chewy). But the pork shank, escargot ravioli, calamari bruschetta, and bucatini were all two thumbs up. The cocktails are also strong and good so don’t skimp on those. But it’s pricey and if I had to do it again, I think I might have chosen the more Asian-inspired, Duck Duck Goat.

As much as I drone on about food, my favorite parts of the weekend involved live music. I have been wanting to attend a Sofar Sounds for awhile now, so I was pumped this past weekend when it actually happened in Chicago. If you haven’t heard of Sofar Sounds, it stands for “Sounds from a Room” and basically musical artists gather in a secret location (it can be a house or a small music venue) and jam for us lucky listeners. They take place in cities all over the world and I can’t recommend them enough. My sister and I were a little skeptical because all we knew was that it was taking place at someone’s house out in Avondale, Chicago. Pushing our nerves aside, we grabbed a wine bottle from a small shop around the corner form Girl & the Goat and ubered over. All of the Sofar sounds volunteers/workers were incredibly kind and welcoming and the other people attending were friendly, warm, and loved live music. We loved each act that performed and it was cool because they were all so different from one another. We sang along, sat cross-legged, and drank our wine from the bottle in a cozy living room. What more could you ask for?

As mentioned above, my other favorite part of the weekend involved Post Animal. We shamelessly went to both of their concerts that were happening the night we were there: one at the Broken Shaker and one at a random house referred to as “Charm School.” As a sidenote, definitely go to Broken Shaker in Chicago–I’m partial to the one in Miami as I mentioned here, but the Chicago one is like Miami’s cool little brother. The vibe at the first show was so cool, laid-back and intimate with amazing projections to add to the experience.

The house party, if possible was even cooler. Literally, I’ve never felt so un-cool in my life by comparison. It was a packed house, but there was something so cool about being in a house, with everyone dressed up, jamming, and $2  pbrs being  sold out of the kitchen. Also props for that house having a gumball machine gilled with tampons, #girlpower. Anyways, it was one of those perfect, magical nights that’s hard to put into words and I’m so glad I got to share it with my sisters.

And last but not least I want to talk about Alinea. I have wanted to go to Alinea since the very first time, years ago, when I stumbled across a picture of its infamous green-apple taffy balloon. Then the more I learned about Chef Grant Achatz, the more infatuated I became. While Alinea was going through a renovation, I dreamed about going to its pop-up restaurant in Miami at the Faena. When I found out we were going as a family I knew I had to make it happen. You have to buy tickets before hand and buy your meal in full. It’s hands down the most I have ever spent on a meal, but I bought it for my mom and I to experience together and I don’t regret it at all. I might have hyped it a little too much in my mind and at times during dinner I felt not-quite-bougie enough, but it was something I’ll never forget. I ate in the Salon, which is the lower-priced option and I don’t want to give too much away/I’m sure there are better pictures floating around the internet, but here’s just a taste of what went down. That’s some Harry Potter shiz y’all.

Chicago you are the kind of city I crave. I am real deep in love and already plotting the next time I can see you again.

Just curious:

1. Are you a cubs fan?
2. If you could only do one thing in Chicago, what would it be?

Curiously yours,

bailey evin

PS As if that wasn’t all enough, I got to dress as my idol Cher, since it was Halloween weekend. I mean, peak life goals accomplished honestly.