In stark contrast to Nobody’s Darling, Dorothy’s is nearly empty, eight customers total, including myself. The space is speakeasy-like, a red door marked “lounge” is your only indication as to what lies downstairs. Dorothy’s is large and luxurious, with rich red wood paneling and art deco wallpaper, lots of potted plants, and velvet couches meant for lounging. Romantic jazz swells over the speakers. I feel like I stepped into an underground Dyke bar of the 20s, reminiscent of my white whale, Le Monocle.

The customers and bartenders are exclusively white, and the fashion doesn’t quite match the sumptuousness of the space. There is an entire menu of bubbly, if you’re so inclined you can purchase $120 bottles of Champagne, to further lean into the Great Gatsby of it all.

My bartender has butterfly clips and peekaboo blonde highlights, a picture of modern Dykedom. They are precise and friendly, with thick silver rings and a diligent expression.

Dorothy’s is the most unique of the bars I’ve been to thus far. Not a neighborhood bar or a nightclub; a true cocktail bar that just so happens to be for friends of Dorothy. It’s surprisingly spacious, a large three-quarter thrust bar is the centerpiece of the space, and there is seating to seat all desires of seclusion. Separated from the bar by a half wall is a lounge with red velvet couches more like beds, meant to be sprawled on by multiple flirtatious Dykes.

Since the crowd is sparse, I mostly focus on the space itself, and of all the bars, this is the place to do so. You can tell every color, every seat was chosen with the utmost attention to detail, creating a space out of time. Real candles illuminate the space, catching the cut crystal glassware at a magical angle. It’s moody and intimate, I wish I were in my suit with a hot Dyke on my lap and a martini in my hand. I feel like I’ve time traveled, but only to the idea of the past, not an actual place in time. Which is probably a good thing, all things considered.

Speaking of martinis, I order Dorothy’s Martini, and it fits the space perfectly, served in a beautiful crystal Nick and Nora. I like beer well enough, but at my heart, I am a cocktail drinker, and I appreciate Chicago Dyke bars for allowing me to indulge myself.

I wonder why both Chicago Dyke bars fall within the realm of cocktail bar when no other bar thus far has come close to this category. You’d think New York would have at least one Dyke bar on their pedigree of world-class cocktail bars. The two Chicago bars are the newest on the list, opened within the last year or so. Is this indicative of a new Lesbian bar trend, or is there something about The Windy City that lends itself to cocktail drinking Dykes?

Dorothy’s feels like it’s trying to figure itself out and establish its place in the hearts of Dykes across the city. There are three bartenders working tonight, all in various mashups of Dyke and bartender style. They seem overall uninterested in chatting with customers or building rapport, which as a bartender, I completely understand. But in a place as new as Dorothy’s, that interaction is integral to building connection and culture within a space. They lounge against the fridge and chat amongst themselves, a slow Sunday evening with coworkers.

Dorothy’s does feel entirely Dyked out, at least tonight, butches and femmes move through the space with ownership. This is the kind of place I would want to take a date, to dress up and slow dance to jazz under the disco ball. I almost wish there was a vintage dress code to fully embrace this outside-of-time feeling.

I can see Dorothy’s blowing up in the next few years, ushering in a new era of Dyke bars that are focused on quality and nostalgia, and my recovering hipster heart is a little excited to be here at the beginning of it all.

Thick framed black glasses: 3

Chicago, IL