The day I left Chicago, I went to the apartment of the man I wrote about in my last post. I spent my remaining three hours getting devoured like he was on death row and requested my pussy and ass as his last meal. I tend to lose track of time when I hook up with this person, so we set an alarm to ensure I’d get a car to the airport on time, but when it went off, I said, “Two more minutes.”
That’s how I feel about Chicago as a whole. I just wanted two more minutes. I really, really didn’t want to leave.
My friend and I were a little nervous about me getting to the airport because my Lyft driver took a solid ten minutes circling the block trying to find us. Once she picked me up, she then proceeded to tell me look out the window because “isn’t that baby so pretty!”, didn’t know if New York City was on the east or west coast, and asked why Chicago sex friend wasn’t coming with me. I texted him this and told him next time, if given the option, I’d pack his mouth in my carry-on because I know what it do. [insert tongue emoji a thousand times]
I adored Chicago. I… liked it better than Boston, which is saying something. I’m still moving to Boston at the end of the trip, but if it wasn’t so far from my friends and family, I’d sign a lease in Chicago in a heartbeat.
I lived my best life there. I stayed in a gorgeous (and very expensive, but worth it!) 3-story townhouse with a roof I ate lunch on every day. I got Classpass and found my love for Pilates again. I ate at many of the best restaurants in the city, wrote at the best cafes, walked around and shopped in the best neighborhoods, hit up the beaches, and went on dates with some fabulous people. I can’t recommend spending 6 weeks in Chicago during the summer enough.
Let’s break it down, once again, into my blog’s namesake, shall we?
I ate a lot here. Chicago is an incredible eating city; nothing will ever top Austin, but I could almost argue Chicago’s on the same level. I didn’t have a single mediocre or disappointing meal here. I also didn’t cook here… at all. I went out for every dang meal.
Gilt Bar: The cacio e pepe… oh my GOD. Get it and the chocolate cream pie.
Honey Butter Chicken: Fuckin’ fantastic. After 5 weeks in Asheville, I vowed to never eat pimento cheese EVER AGAIN, but their pimento mac and cheese was divine.
Bad Hunter: If you go here and don’t get the potato fry bread (with burrata and cherries), I’m pretty sure you’ll get arrested. The menu is seasonal (though I think the fry bread is a staple), but if they still have it, get the beef kabob on polenta, too. Great mocktails, too.
Little Goat Diner: Get the crudité platter (it comes with homemade naan with everything seasoning on it) and the “One Twisted Sundae.” The latter is a fudge brownie topped with pretzel-flavored ice cream, caramel sauce, whipped cream, and pretzel pieces. It was divine. I came back and got the turkey club, which was so damn good and, remember, I’ve tried the best delis in NY and Boston.
Clever Rabbit: My friend told me their burger was “stupid good” and she was right. Best burger I’ve eaten in my life.
El Metro Cantina: These tacos are better than the ones I had in Austin. Get the chicken tinga and the pork. Their red and green salsas are legit.
High Five Ramen: Get there early (like 4-4:30pm). The wait can get up to 4 hours and it’s a twelve-seat establishment. Get the classic ramen, half-spice. It was delectable.
The Violet Hour: Really cool speakeasy in Wicker Park. I love how it’s designed. Strong drinks.
Café Baba Reeba: I usually don’t go for tapas places, but everything on this menu was delicious. I loved the fried chicken thighs, beef kabob, stuffed mushrooms, and burrata. I enjoyed this place so much and couldn’t make it there during a week I was on deadline, so I had it delivered. I ordered the chicken and mushrooms again, as well as their garlic potato salad and Brussel sprout and manchego salad. Incredible.
Gyu Kaku: There are a few of these across the country and when I’m back in NY, I will *absolutely* be hitting it up. I love Japanese barbecue, but sometimes it can get expensive. This place was very reasonably priced and all the food was delicious. Get the jelly sake. It’s so weird and yummy.
Stan’s Donuts: Classic glazed is where it’s at. Game over.
Sawada Coffee: Their black camo latte made me see God. It’s matcha and espresso, which, yes, I KNOW it sounds disgusting, but it turns out it’s DELICIOUS and tastes like chocolate. Get it with almond milk instead of regular milk. Just trust me.
3 Arts Café: Chicago sex friend recommended this place and holy shit. It is my dream place to write. I thanked him profusely. (Get their fries with garlic aoli and their warm chocolate chip cookie + a cup of coffee. Yes, I am aware that I eat like a raccoon.)
Beaches: I tried going to Oak Street beach, but it was closed for an event, so I walked 15-min north to Long Avenue Beach. I was warned by a friend that it would be crazy busy and, yep, it was. But I enjoyed it nonetheless. I liked Kathy Osterman Beach much more. It’s a little bit of a hike and is nicknamed “the gay beach,” so, out of respect, I shamelessly flirted with a very attractive woman while wading up to my waist in the FREEZING COLD water (and got her number).
Movie theaters: I took the blue line to Logan Theater and enjoyed this super cute place until the film “Eighth Grade” DESTROYED ME. I also went to a “Clueless” shout-along (where the audience all quotes the dialogue together) at The Davis Theater with my friends and it was fabulous. The theater was gorgeous.
Workouts: I highly recommend Ascend for their classic reformer class with an instructor named Sheridan; she’s a sweetie. I also like Pilates Pro Works’ machine classes if you want a challenge. If you like aerial silks, Air is fabulous. Challenging, but incredibly fun.
Wicker Park shopping: Wicker Park is a very cute area. It’s essentially the NYC East Village equivalent. I went to Penelope’s—a super affordable option—and bought a cute lil’ cotton off-the-shoulder black romper that makes me feel like Audrey Hepburn if she was into toddler cosplay. I also went to Una Mae’s (slightly more expensive) and bought a delicious white cotton shirt and long, dark navy bodycon dress. But my favorite shop was Moon Voyage (very pricey, unfortunately), where I impulse bought an expensive slinky black dress for absolutely zero reason (I’ve been dying to find a dress like this for years though) and this light pink silk tie-front top.
I wore that shirt to coffee with Chicago sex friend and he told me it was very distracting. I told him it was payback for him sales technique-ing me. :)
When I first got to Chicago, as I’ve mentioned in previous posts, I went on a date with a 24yo for the first time in my life. I’m a 30yo woman who, all throughout her twenties—with the exception of someone who was 26 when I met him—dated older, this was an experience that made me laugh at myself. But, as I’ve written earlier, he was great. Incredibly intelligent and eloquent and a total cutie. But our schedules just didn’t sync and we fell out of touch. No harm, no foul. He was cool.
Next, I went out with someone hilarious, but there was no sexual or romantic spark for either of us. I did want to hang out again as friends, but, alas, I couldn’t find the time. He was cool, too.
Then I went on a date with a super adorable woman in an open marriage who I really liked! She did pole-dancing and I really wanted to go to a class with her, but then she had a family emergency… and then my job got crazy… then I got strep throat… and our schedules didn’t mesh. I felt horrible because I truly did want to hang out again—I wasn’t trying to pull a slow fade or anything—and I actually did want to redeem the “one free threesome” coupon she kindly offered to me on behalf of her and her hot ass husband, but, AGAIN, it just didn’t work.
About three weeks before I left Chicago, I met the gorgeous dude from my last post who I ended up hanging out with for the rest of my time here.
I do not regret this choice.
In all, everyone was fabulous! The Chicago dating scene is great! I only went on one “bad” date, which I’ve written about in the next post. And it wasn’t even bad because I thought it was hilarious.
Chicago, you are tied for first place with Boston. Not sure how that happened, but you are. I rerouted my drive home to return for a few weeks next month. Maybe I’ll be living there permanently in a few years… Who knows.
Dana Hamilton is a writer from New York City currently traveling across the United States on her own for all of 2018. Passionate about everything having to do with the body, she writes about sex, dating, relationships, body image, and eating disorder recovery. She is a frequent contributor to Playboy and her work has appeared in Cosmopolitan, Marie Claire, Teen Vogue, New York Magazine, Time Out NY, and SELF, among other publications. Before she became a freelance writer, she was an editor at two "Big Five" houses in the book publishing industry. She has also written four books (under a pseudonym) for HarperCollins and is currently working on her fifth novel. She holds a BA in writing and nutrition from New York University.
Passionate about everything having to do with the body, Dana Hamilton writes about sex, dating, relationships, body image, and eating disorder recovery. She is a frequent contributor to Playboy and her work has appeared in Cosmopolitan, Marie Claire, Teen Vogue, New York Magazine, Time Out NY, and SELF, among other publications. After driving (and dating) across the country and back on her own for all of 2018, Dana now splits her time between New York, Boston, and Chicago. Before she became a freelance writer, she was an editor at two "Big Five" houses in the book publishing industry. She has also written four books (under a pseudonym) for HarperCollins and is currently working on her fifth novel. She holds a BA in writing and nutrition from New York University.