We’re continuing VinePair’s new Shift Diaries series with a trip to the Windy City, asking real bartenders around Chicago how much they earn in tips on a typical Friday night, what their crowd is like, and what everyone around town is drinking. VinePair asked bartenders working everywhere from a Ravenswood brewery to a pop-up restaurant in the West Loop to chronicle their shifts from happy hour to last call.

Name: Antonio Moreno
Age: 32
Location: Cultivate by Forbidden Root
Pronouns: He/His
Total Tips: $300
Shift: We usually have about four servers and two bartenders working, and we are pretty booked throughout the entire night. We just opened up our patio, so now we are getting a lot more business from people seeing us outside. We’re in a weird area next to some construction currently, but the patio definitely helps bring people in.

Usually, I get in around 2 p.m. on a Friday. We open at 3 p.m. and then for the first few hours, we’ll get some happy hour business. We’re getting a few people who work in some of the offices around us. They’ll come in with their laptop, and they’ll get a few beers. We also offer half off all of our bar snacks, so people will get some popcorn or chips or the fried chicken skins, which are fantastic with pimento cheese, and they’ll get a flight, which is discounted down to $10. We get a really good crowd of happy hour people just posting up to the bar. Not so much table-wise, but a lot of bar patrons, so it’s a nice start to the day. For the most part, it gets really busy around 6 p.m. or so, and then we’re usually good all the way until about 9, 9:30, and we close at 10 p.m.

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We are a brewery, so we sell a half-and-half mix between beer and the cocktails that I’ve created. It’s a little bit of a wealthier area with a lot of family types, so we do a lot of Old Fashioneds and Martinis. We offer three versions of Old Fashioneds: our typical whiskey Old Fashioned, a Mezcal Old Fashioned, and a Rum Old Fashioned. The Mezcal Old Fashioned is probably the second best-selling drink, and the rum is pretty new, so that one is still growing.

There are constant questions about the beer. I try to stay as informed as I can about our process from the brewers. We offer a house flight of 5-ounce pours, and that is the No. 1-selling beer item just because you get about a pint and a half or so. Or, you can make your own flight if you like, but we offer our house flight for a discounted rate, so it is very, very popular. Every once in a while, I serve a couple of beer cocktails to try to incorporate some of our beer. I have a Cosmo Charleston, kind of like a Cosmopolitan. It uses Koval cranberry gin and also some of our IPA. It’s one of our GM’s favorite drinks I’ve ever made for him. I’ve also done a Malt Row Mai Tai because the strip of Ravenswood Avenue that we’re on is called the Malt Row because there’s so many breweries. I have some homemade orgeat and some Malort in there, so it’s nice Chicago Mai Tai.

We’ve only been open for seven months, so I don’t have super-crazy stories yet to draw on. There was one weekend that our air conditioning broke, and I thought I was going to die because I was just so hot. The beer was helping.

Name: Kyle Bagley
Age: 53
Location: Graystone Tavern
Pronouns: He/His
Total Tips: $350-$400
Shift: We’re kind of a local watering hole with Wrigley Field in our backyard. Usually, it starts with regulars and then towards the middle of shift, you end up with strangers and people that may not always be in the neighborhood coming to check it out. There’s a couple who are close to retiring and they always come in, and that’s how I start my shift — slowly getting into the groove, talking about their week and the regulars’ week.

If we have a DJ playing, he starts probably around 10 or 11 p.m. and then the mood and the conversation gets a lot more lively. And I get a lot more lively because I get some libations in me. The party really gets started around 11.

Our demographic is really interesting here. It goes from 22 to 60 years old. Typically, we pour a lot of draft beers. We have some really cool local beers that we feature here, and then we have some specialty cocktails — Old Fashioneds and some other things. We watch a lot of golf here, so we do some Transfusions and some golf-themed cocktails, and those seem to be really popular this time of year.

A lot of people move into the Wrigleyville neighborhood when they’re done with college because there’s still affordable apartments here. Every year, you have an influx of new blood, so you have a whole new time of discovery with them, learning who they are, and then they get a different job or they move to a different neighborhood to get out of the madness that is Wrigley.

What’s kind of sad is that as the neighborhood gentrifies, they’re tearing down a lot of the three-flats and they’re putting up single-family homes, so we lose the nuances that made the neighborhood so interesting. I’ve been in this neighborhood forever. Most people in the neighborhood used to be looking for a deal: “What can I get for $3?” We used to run these specials where we’d do three hours all-you-can-drink for $20 or $30, but as the neighborhood has changed, so has that clientele.

People now expect a cocktail program. They expect you to have excellent beer choices and excellent liquor choices, and your back bar has to have everything in it. We have to have great food. Before, I could have frozen chicken tenders, and nobody gave a shit as long as they were getting something in their belly to absorb more $3 vodka. Now, we have to really, really be conscious about what quality of product we’re putting out there and making sure that we change our menu to reflect seasonal changes and make sure that we’re using locally sourced and fresh ingredients because people really pay attention to that stuff now.

Name: Cinthia Miranda
Age: 43
Location: Sueños at Soho House
Pronouns: She/Her
Total Tips: $300
Shift: It’s a good vibe. We have people that come in for happy hour, getting off of work in the West Loop. It gets busy around 4-5:30 p.m. and then it dies down for a bit and we get our first round of dinner reservations around 5:30-6 p.m.

During the course of a happy hour, I’m mixing 40 to 50 drinks. It’s more Micheladas, which we serve with our Michelada mix and a Pacifico draft. They come with chamoy and Tajín and an oyster to top it off. People really love it. We definitely prep a lot. We put a lot of time and energy even into the garnishes. We have pineapple that we slice and put chamoy and Tajín on and put it in the dehydrator for four and a half hours.

We have specialty drinks that were done by our beverage director, Danielle Lewis, that are influenced by Baja, San Diego, and also a little bit of New Orleans and Spain. We mix mezcal and tequila with piña, guava, and a little bit of dried chili and make that into a Spicy Margarita. We also have all-artisanal tequilas and all-artisanal mezcals, so you’re not going to find your typical celebrity tequila like Casamigos. I’ve been seeing people just wanting something very simple, where they taste more of the tequila or the mezcal, maybe on the rocks or neat or with a splash of lime juice.

People are coming in being curious about this pop-up. They’re asking “How long are you guys here? Do you guys have a brick and mortar? Are you staying in the neighborhood? If not, what other neighborhoods are you looking at? Can you tell us a little bit more about the chef? I’ve followed him. Can we speak to the chef?” Everyone always wants to speak to the chef, which he is open to. He loves talking to everyone.

Name: Sean McQueeney
Age: 27
Location: The Owl
Pronouns: He/His
Total Tips: $300
Shift: Lately, we’ve been doing a lot better because of summer weather. I was not at work last Friday, but two Fridays ago was just a normal busy summer day. It was really warm. People showed up around midnight, and then 2 a.m. hit and then we got even busier. The DJ played Blink-182, and everybody screamed the words. They just ate it up. It was very funny.

The crowd is more on the younger side, people who want to hear live music on the weekends. We serve a lot of beer and a lot of shots. We have a new cocktail program with a lot of good summer drinks. It’s mostly beers and shots after 2 a.m., but anytime before then, I’m making a lot of cocktails: Old Fashioneds, Margaritas, and a few of our house cocktails.

We get a lot of the industry folks who come in after their shifts. Mostly, we’re just asking how each other’s days have been, and how the week is going. Some people I know better than others, so I can ask more personal questions. Over the four years I’ve been at the bar, I’ve met a lot of people. I moved out of Michigan to get away from everybody I knew, and now it’s ironic because I know everybody again.

But I like having regulars. They help pay my bills, so that’s first and foremost. It’s good to have a relationship with the people that you work in the neighborhood with and kind of vent about something that went wrong or share something that went great.

At 4 a.m., people will close out their tabs, get one more drink, and ask their friends if they want to do a shot. In the summer, people don’t really mind going outside to wait for their Ubers. In the winter, people don’t want to leave, but our staff is polite enough. We’re like, “OK, we need to get you out of here.”