When it comes to grabbing a cocktail, old standbys are great. Mostly. It’s nice to have a go-to spot when you don’t want to overthink things or get too crazy.
But old standbys are just that – you’ve been a million times. You probably also gravitate toward the same cocktail (guilty!) And chances are if you always hit up the same spot, a lot of other people do too.
There is something to be said for that feeling you get when you break away from the norm and lead your friends to a really cool spot they’ve never heard of before. Sort of like “YAAS – brownie points for me!” So where are those places in Chicago? Check out this list of some of my favorites:
The Berkshire Room is a bar in the ACME Hotel and it is literally my FAVORITE spot to take friends that mostly have never heard of it. (Okay, yes, that sort of means it’s one of MY standbys… but there’s enough variety to keep things interesting). The best part about it is that they have a drink called Dealer’s Choice, which isn’t so much a drink as a free-for-all of boozy possibilities.
Essentially, you pick a spirit base (I always love gin) ideal flavor palette – I usually go for herbaceous – and your favorite drinkware. I always go for whatever the bartender recommends, but I also have found a mad respect of the coupe glass. You will never get the same drink twice, and you will learn all about the spirits and the ingredients as the bartender weaves a story about them of science and deliciousness.
Lost Lake is very similar to Three Dots And a Dash… but way less crowded and expensive. Plus, it’s an excuse to head to Logan Square (and Avondale) and explore! They have an amazing cocktail selection (they had a fire a while ago and are still getting caught up with the kitchen) and plenty of adorable booths and barstools from which to enjoy them. I always love the Stranger in Paradise, a boozy mix of tequila, pineapple, lime, cinnamon, allspice, absinthe and a whole bunch of other exotic ingredients. And this place is great for groups – they’ve got a ton of punchbowl inspired drinks to share!
Violet Hour
You may have heard of the Violet Hour but I’m putting it in here for the benefit of the many who probably haven’t. It’s a speakeasy-type joint in Wicker Park hidden by a big beautiful mural across from Big Star. This is the perfect place to take your girls for some quality conversation or for an intimate date, all velvet drapes, high-backed chairs and low candlelight. You can’t go wrong with the great selection of drinks either! Just be mindful of the House Rules – no phones out at the table! (Or Jager Bombs, for that matter).
Upstairs at Le Colonial
Riley and I ate here a few years ago for his birthday (Le Nomad is an amazing fusion of French and Vietnamese cuisine) and during our visit I was reminded how freaking cool the upstairs bar and lounge area is. When they aren’t hosting private events, the space is perfect for date night. The giant fans, regal wicker furniture and intimate vibe makes a great place to sip martinis and pretend you’re in another country!
This is one of my other very favorite hidden cocktail spots in Chicago – and usually when I tell people about it, they have no idea it exists, which is even better! This spot will make you think teleportation is real. Underneath Green Door Tavern is a room that was actually used as a speakeasy during Prohibition. After that, it was primarily used as a storage space - gone but not forgotten. Eventually it transformed into somewhat of a private event space, and finally into the historical escape it is today.
Attention to detail is everywhere you turn – from the giant American flag hanging on the wall to the cocktail menu on Tarot cards. The cocktails are just as cool –this was the first time I had ever had a shrub cocktail (check out how I recreated the recipe here), which is a variation of the drinking vinegars popular in the 1920’s. They also have performance artists and burlesque dancers many evenings.
Booze Box
I always consider Booze Box to be a bit of a speakeasy – especially because of the way I discovered it. While readily available to research on their website, Riley and I actually stumbled into this one by chance. We were going for an evening walk in our new hood (the West Loop) and noticed an alleyway with a giant red arrow across from Green Street Smoked Meats. I figured it was a weird thing to have on a building if it didn’t lead to something… so I walked down the alleyway a little bit. I noticed there was a door, and Riley thought it was probably the kitchen. I had a feeling it was something else and decided to be bold and open it – which revealed a staircase. Feeling stranger by the second but also curious as a cat, we walked down them – and straight into a hopping bar scene.
Booze Box is right below Sushi Doku and has both a great selection of cocktails and Japanese Izakaya-style plates and street food. It’s a good late-night spot – on the weekends it’s open until 2 AM. Too long of a wait? You can always head over to RM Champagne Salon or Nellcôte!
Is there a hidden bar I missed? Let me know in the comments!!
