Where to Drink (and Eat) Alone in Chicago — A Girl's Guide to Drinking Alone

By Joanna Carpenter, Guest Writer

Hello, fellow GG fans! Joanna here, excited to be dropping in as a guest writer to share my favorite places to drink and eat solo in Chicago. I spent a weekend in the Windy City recently and let me tell you—Chicago does it right. The hospitality, the creativity, the vibes: you name it, they've got it.

I'm a serial solo diner. I fully believe that one of the great delights of life is plopping down at a bar with a book and enjoying a hospitable moment without your bubble getting invaded by a guy who can’t comprehend that you do indeed find Careless People more interesting than him (also if you haven't read Careless People, you should).

The thing is, going solo seems to be getting even tougher these days, especially in New York. I think the emotional hangover from the destructiveness of the pandemic and the drastic shifts in guest behavior (largely for the worse) play a huge part in making going out solo difficult, and have also impacted our hospo-ecosystems more than we even realize. I also think, point blank, that there is still an undeniable undercurrent of misogyny that ripples through our service offerings and larger culture, which I'm pretty sure was part of the onus of Sammi creating A Girl's Guide to Drinking Alone to begin with! (Editor’s Note: it was!)

To that end, Chicago was a breath of fresh air, a very tasty adventure, and a lesson in what true hospitality can and should be. What's more, they're not trying to prove anything to anyone. It's simply the way things are, from the unapologetic PSAs of prices being higher because a restaurant insists on giving its staff healthcare, to the thoughtfulness and personal touches that are such a reflection of the spirit of the midwest. For those of you going solo, here follows a detailed (a.k.a fangirling) love letter to some of Chicago's special places. Hope you enjoy!

*Shrimp & Grits and a Bloody Mary at Little Goat DIner*

Let's start with the Little Goat Diner.

This airy, retro-coded spot is the sister restaurant of the famous Girl and the Goat from Chef Stephanie Izard. This was actually my last meal in town after my friend Brandon insisted I go. I stopped by on my way to O'Hare, perfectly timed to avoid the Sunday rush. The host guided me over to the counter, and I got to sit with my book and peek through the service window into the bustling kitchen. Stephanie Izard's menu pays a cheeky homage to her Asian heritage, and the Bloody Mary I started with was perfectly balanced and zesty (also why aren't more people putting kimchi in their Bloody Marys?!). One of the dishes the Diner is known for is their Shrimp & Grits. Now readers, I listen to my Southern friends when they tell me how to be picky about grits, and I think they'd be thrilled by this iteration. The shrimp were perfectly tender, the grits were delightfully creamy with just the right amount of salt and cheese, and the texture popped with the addition of braised pistachios and brussels sprouts leaves. My sweet server was kindly non-judgmental when I basically mutated into the Beast from Beauty & the Beast, slurping his big bowl of oatmeal; some dishes are too delicious for dignity.

All in all, Little Goat Diner is a perfectly breezy visit, ridiculously tasty and fun to sit at the counter solo.

*Steak Frites Sandwich, a Bloody Mary, and Joanna’s reading of choice at Obélix*

Up next is Obélix, a beautiful yet unpretentious French spot suggested by my friend Alicia, who always has my complete faith when it comes to food recs.

When I arrived for brunch at the bar on Saturday, there was a nice mix of solo diners and couples and the mood was relaxed. I started off with a Bloody Mary (shout out to going two for two on great Bloody Marys) then dove face first into the Steak Frites Sandwich on the bartender's recommendation. When I came up for air (again, zero dignity, only vibes), we got into a lovely discussion about everything from people watching to current events to allergies murdering our collective sinuses and it was silly and delightful. I wrapped up with one of Obélix's special pastries: a flaky croissant stuffed with fluffy sweet cream and pomelo gelee, paired with a glass of dry, zippy rosé cremant. The bartender and I continued to bond over our favorite pairings, and by the time I waddled out of the restaurant I was already planning my return visit - 10/10 for everything.

Of course, I have to mention my jaunt to The Green Mill.

You probably know at least a little bit about this iconic Prohibition-era jazz club and its history as a favorite haunt of Al Capone and Billie Holiday. I always find that spots like this can be hard to visit solo, especially as a woman. Very often you're surrounded by couples in full romantic throes (and to be fair I did have to ask the couple next to me to stop leaning on my leg as they got quite cozy), or it's so crowded you end up edged into an awkward corner, or you get some tourist bro insisting on mansplaining to you about the whiskey that you ordered while he talks over the music you came to hear. Not so with Green Mill. I was able to snag a seat at the long, snaking bar and while it was crowded as always, management there does not mess around when it comes to guests respecting each other and the performers onstage. The bartenders are wizened, effortlessly slinging drinks with the perfect amount of "seen it all" snark. Gloriously, management requires quiet when the band is playing, unlike clubs in New York. This meant that a couple hundred of us were piled into this legendary place, all respectfully, quietly sipping and basking in lovely music. It felt sacred, even though to the staff it was probably just another Friday. Finally, and I know that perhaps this is a small thing, but: as someone who constantly hydrates when I'm out, I'm always so appreciative of bartenders who will keep refilling my water without making me feel like I'm bothering them. The folks at the bar were kind and diligent about keeping both my water and my glass of cheap Sauvignon Blanc full, and when I wandered into the night after the set was over, I was more grateful than ever for the existence of old places like The Green Mill, where a girl can still sit unbothered and sway to some tunes alongside everybody else.

*Saffron Tagliatelle and a glass of Trebbiano at Giant*

Okay. We must talk about Giant.

Is it slightly out of the way if you're staying in downtown proper? Sure. Should you care? Absolutely not. Another recommendation from my friend Alicia that I am delighted to pass along to you, Giant does not actually have a bar. It's a small, maybe 12-table spot plus a chef's counter, and you're going to want to make a reservation. I hadn't realized that there is no bar, and started to slightly panic at hearing that they were booked up with reservations, buuuut, since it was still early and I had to be out fairly quickly to catch a show, the host kindly tucked me into a corner table next to a shelf full of amari, where I really got to observe the dance of the dining room. My server greeted me with, "I'm so glad you're here, and I love that it's just you and your book!" I'm sorry - what?! Okay, fine. I live here now.

The restaurant was packed (it was a Saturday evening, after all) and he still took the time to walk me through the menu, asking about my favorite flavors and nudging me toward his personal favorites. I started with an Amaro Nonino and soda ("Oh, that sounds brilliant, I actually need to drink that more!") and their broccoli with chickpeas and roasted garlic. It was here that I discovered that a bowl of broccoli can actually be a religious experience. Who knew?

I followed with his recommendation of their homemade saffron tagliatelle piled with fresh dungeness crab and chili butter, paired with a bright, briny Trebbiano that had a bit more skin contact than usual and friends, I truly could have cried. I'm writing this weeks after the fact, and I'm still thinking about this meal. When I needed to head to my friend's show, my server seemed genuinely sad that I couldn't stay for dessert and when he dropped the check, he surprised me with a scoop of their housemade ice cream and brushed off my thanks with a wink, a wave of his hand, and a “see you next time!” Giant really is an emblem of excellence–go there, especially solo, and let yourself bask in the delicious, delicious love.

Finally: Kumiko. Dear god…Kumiko. Honestly, as I write this, I'm not even sure where to start as there isn't sufficient enough poetry in the English language to describe the experience.

Is it okay to cry at this bar? Literally asking for me.

Chef-Owner Julia Momosé has built a space and brought together a team that are an utter beacon of care, talent, and creativity. I've known Julia for a few years now just through industry circles and have always found her to be inspiring, so I was thrilled to finally have the opportunity to sit at her bar and experience the magic of Kumiko. (I went on Friday evening in the midst of all the awards buzz for the restaurant which will only get buzzier so you’ll definitely want to make a reservation.) The space feels sacred yet entirely unpretentious. The food is elegant and delectably clever. The cocktails are brilliant - playful yet unpredictable. Sit and let Maddy tell you the stories of her favorite bottles while you're making your way through each dish, and make sure to get Bridget's opinion on any of that day's special offerings. Oh, and if you can, head downstairs to the new whisk(e)y bar and sip on things you'll not be able to find anywhere else, lovingly nicknamed “Julia's suitcase bottles.”

*Truffle Milk Toast (aka the best dessert in the world) at Kumiko*

It occurred to me throughout my meal that a lot of us often go to bars and restaurants rushed and harried, acting like we already know everything, that service should be predictable, that we are there to consume, not to experience, like food and drink are obligatory things to be crushed and sped through. Kumiko gracefully, tenderly reminded me that every bite and every sip are actually fleeting opportunities for us to slow down, moments to be present in rather than control…there is always a new story to tell and a new bottle to discover, if you just let it happen. As I sat alone at this beautiful bar, I counted myself lucky to simply enjoy an evening of basking in the delight of an experience that was one of a kind—divine—and that's exactly how it should be.

Thanks for the hospitality, Chicago. I'll remember the Malort next time.

—Joanna

Little Goat Diner - 3325 N Southport Ave, Lakeview

Obélix - 700 N Sedgwick St, River North

The Green Mill - 4802 N Broadway, Uptown

Giant - 3209 W Armitage Ave, Logan Square

Kumiko - 630 W Lake St, West Loop

Joanna Carpenter is a Broadway actor who spent over two decades in the food and beverage industry. She is the founder of 86 the Barrier, a language learning program created for Spanish speaking immigrants and hospitality workers. Her favorite pairing is a good glass of bubbles with Flamin’ Hot Cheetos, and she believes that a nice conversation is always more important than a fancy mise en place. IG: @thejoannac