The Best Bars in Chicago No Matter What Your Going Out Style Is

woman in berkshire room chicago

When the drinks flow faster than the river running through the city, I know I’m in my kind of place. Chicago is filled with great food and endless cool things to do. But as a bartender, I always appreciate a great place to have a drink. Having a guide to the best bars in Chicago is a must for your visit.

I’m not very picky when it comes to bars, as long as it’s approachable. I don’t like anything to be too much. I enjoy fun and creative cocktails as much as I enjoy a bottle of Bud Light. And I hate being judged for either choice. It all depends on what I’m in the mood for.

What matters most to me in a bar is atmosphere, where the patrons are friendly and the bartenders aren’t condescending. I was pleasantly surprised to find out that Chicago is filled with hip cocktail bars with none of the pretentiousness, as well as plenty of ratty neighborhood dive bars to choose from. Whatever mood I was in, Chicago had me covered.

Explore more helpful posts on Chicago:
  • Read my list of favorite restaurants in Chicago here.
  • Read how to spend the perfect three days in Chicago here.
best bar in chicago the berkshire room
I had no idea that behind this sign would be my favorite bar ever.

The Berkshire Room

I’m starting with the Berkshire Room at the ACME Hotel. That’s because it is hands down my favorite bar I’ve ever been in, period. This is not a bar I read about before arriving in Chicago so I was doubly excited to find this gem. Actually if I’m being honest, my boyfriend read about it when we were out and about on the Louis Vuitton City Guide app that he had downloaded for our Paris trip.

That’s how I found myself sipping delicious cocktails at this hotel bar.

The prettiest bar I’ve ever been in.

The bar looks like an old Spanish mission but with a modern feel to it. The bartender was whisking up craft cocktails in a short-sleeved flannel and Chicago Bears hat. He looked like he belonged at the neighborhood country bar I work at in New York. With only a few other customers in the bar due to the fact we were in there before the work day ended, he started chatting us up. Of course “just one drink” turned into a few cocktails.

For how nice the place is, the drinks are extremely reasonable. Also, going before the end of workday happy hour rush made for a very relaxing environment. The bartender said the place starts filling up with suits once 5 o’clock hits. Depending on your drinking style, you might want to show up for a mid day cocktail. Unless of course you’re the after-work drinks mingling type.

interior of the prettiest bar in chicago
The Berkshire room is beautifully decorated and still you can walk in off the street for a drink.
cocktail on bar at berkshire room
Did I mention heavenly cocktails?

Three Dots and A Dash

I saw one picture of the extremely over the top cocktails at Three Dots and Dash and knew I had to go there. The most important thing to note though is it’s a little hard to find. The address will map you in front of a Southern BBQ spot, with no tiki bar in sight. The actual location is around the corner, through the alley, directly behind the BBQ place.

This bar is extremely dark which made pictures difficult. One of the biggest struggles of being an aspiring photographer is that I never want to actually lug camera gear around. Sometimes that’s a good thing though because in a bar like this I can only make so many attempts at a decent photo before I put the camera away and focus on my surroundings.

Pricey, but worth it.

For how insanely packed the place is, the bartenders are way too nice. They are mixing up drinks with five or six ingredients each. Then topping them with some of the most intricate garnishes I’ve ever seen. Yet they are still extremely friendly and offer a lot of help with the menu.

At about $15-18 a cocktail, they aren’t cheap. And since they actually taste like something you would be drinking on a beach somewhere, I could only stomach one. I don’t typically like sweet cocktails and even if that’s not your thing, this bar is an absolute must for anyone who appreciates a well-done cocktail bar.

three dots and dash coaster on bar
The ambiance of this speakeasy screams date night.
cocktails at three dots and a dash
I couldn’t imagine putting endless amounts of these together in one bar shift.

Bad Hunter

If you read my post about the best Chicago restaurants, you will know that the best burger you will ever find in your life is at Au Chevals. The bar and restaurant right next door is the best place to sit and have a drink while you wait for your table to be ready.

Since I already had my dinner planned, all I could do at Bad Hunter was have a few cocktails. I find it so regrettable when I stumble onto a place where the people are so nice and the atmosphere is so perfect but I know I’m limited on time. I hate that I’m just one person with a stomach only so big and I can’t consume everything on vacation. Gluttonous, I know.

The friendliest staff who will ever serve you.

The bartender started talking to me and my boyfriend when I pulled out my camera to take pictures. I was immediately up and out of my seat when I saw the window peaking into the most beautiful restaurant kitchen I have ever seen. It wasn’t until the bartender asked if I wanted to go into the kitchen to take pictures that I absolutely fell in love with this place.

She had already checked with the chef to see if he would let me in and he agreed. Now I don’t know about you, but I work in bars and restaurants and that’s something most wouldn’t ever do. The food coming out looked incredible. This place is definitely on my short list for my next trip to Chicago.

dirty martini and menu at bad hunter
A perfectly made dirty vodka Martini, yes please.
cocktail at bad hunter
The teeny tiny clothes pin – I can’t with the beautiful details.
inside of kitchen at bad hunter
I want this kitchen in my apartment in New York, staff included please.


You ever been out in a city and see a place that just screams you? A bar, a clothing shop, or maybe a café – and you know you have to go back when you actually have the time to go in? I walked by Rossi’s one morning and knew it was my kind of bar.

I was also pretty sure I made a mental note of the name and location to come back to so I wouldn’t forget. This place was only a few blocks from my hotel so of course I would find it again, right? But it actually proved to be just a little difficult when I couldn’t remember the name and started Googling dive bars in the area.

It wasn’t until I got out on foot and looped through the city retracing my steps that I actually stumbled onto it again. After I had built it up so much in my head, I was concerned that it might let me down. Luckily, It did not.

The bartender just sealed the deal.

Now I appreciate a bar with a distinguished looking bartender more than anything. The older guys with raspy voices from too many cigarettes or the women with tattoo sleeves and leather skin. You know what I mean, the career kind of bartenders who are a little rough around the edges. The ones who know that being a bartender goes beyond just knowing how to make drinks.

If you can imagine that bartender then you can picture the man behind the bar at Rossi’s with his 80s rocker haircut, in a Cheerios shirt and hippie glasses. If you can do that, you can also imagine what Rossi’s is like. So if you want something unrefined and a little unpredictable, a night drinking here is exactly what you need.

rossi's dive bar entrance
The world’s most perfect dive bar.
inside dive bar rossi's in chicago
The epitome of a dive bar is a cash only sign.

L & L Tavern

Like most travelers, I rarely visit any destination without consulting Anthony Bourdain. And like most travelers, I was deeply affected with the news of his death. I’ve never really understood how people react so passionately to celebrity deaths, but Anthony Bourdain changed that for me.

Which made L & L Tavern one of the most memorable places on my trip. Before the Cubs game, I wandered over to this extremely large hole in the wall. With a self-proclaiming sign declaring it the “creepiest bar in the USA,” you can imagine the unease I felt walking in.

It was pretty quiet, except for a few patrons at the bar and the guy behind it, who appeared to be more in his living room than tending bar. The only TV in the bar looked to be about as old as me, and was playing Jeopardy on full volume.

A shot of Mallort for Anthony Bourdain.

What I ended up doing in this empty bar was make friends with the bartender, who happened to be the owner who was featured drinking with Anthony Bourdain on his show. I had my first (and only) shot of Malort – the Chicago liquor that tastes like the sound tires make when they skid across a blacktop.

After a few shots and beers, I headed to the game feeling a little closer to Anthony Bourdain.

mallort magazine ad on bar in chicago
Have a shot of Malort, but also, don’t have a shot of Malort.
beer in koozie on bar
The koozie goes everywhere.
interior of l & l tavern
And again with the cash only sign.

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