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    Whiskey Business - Holly Jolly Pop-up!

    3.4 (437 reviews)

    Whiskey Business - Holly Jolly Pop-up! Photos

    WHISKEY BUSINESS - HOLLY JOLLY POP-UP! ATMOSPHERE

    What's the vibe?
    Moderate noise
    DJ
    Casual
    Outdoor seating

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    Recommended Reviews - Whiskey Business - Holly Jolly Pop-up!

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    Biscuits and gravy baby
    Danielle R.

    Looks can be deceiving but you do not want to pass this place up. The drinks are good, like really good. And the food? Off the charts for the bar vibe they are going for. Highly recommend coming in for brunch; biscuits and gravy are fire and the chilaquiles might just be the BEST I've ever had. Service was bomb, do yourself a favor and ask Billy for an espresso martini. The cherry on top is the rentable Rooftop!

    Katie C.

    If you're looking for that summer vibe this is definitely the bar for you. Their outdoor seating has lots of sunshine and umbrellas for coverage. Ordering is super easy - with the simple scan of a barcode you can have everything delivered straight to your table. We still had our waitress check in on us periodically to make sure all of our food/drinks were coming out. There's lots of activities to do in the outdoor area as well. They had a cute unicorn spray water, connect four and a big jenga. There are a ton of drinks on the menu - I was surprised to see my favorite the 'dirty Shirley'. The food was also super delicious. Hands down one of the best experiences.

    Chicken and waffles
    Emma S.

    Great rooftop with really fun 80s neon decor (big fan of anything neon). As you'd except, they have good whiskey based drinks, as well as many other cocktails. The brunch platters were delicious- the French toast and chicken are must try's! Looks like they do outdoor movie events during the summer, and have a decent number of TVs to catch any sporting event that happens to be on. Even when raining the rooftop is a great hangout spot

    Breakfast sandwich
    Mirella K.

    It was my first time at Whiskey Business and I had a lot of fun! My friends and I reserved a little ski chalet room specially made for the holiday season for our friend's birthday brunch. Whiskey Business has 2 floors with a rooftop patio that's vibrant and cute! The ski chalet we reserved was on the rooftop. Reserving the ski chalet was $65 and it was so worth it - it was super cute, warm, and we truly felt like we were at a ski lodge. It was perfect for the holiday/winter season. It wasn't busy even though it was brunch time on a Saturday (thank goodness)! Our food was reallyyyyy yummy - we got the avocado toast, buffalo soldier fries, and breakfast sandwich. Everyone loved their meals and the prices were super affordable, too! Our cocktails were alright, they were pretty small and nothing too special. Our server was alright too, she wasn't really friendly and seemed annoyed we were asking questions about some food items on the menu. Whiskey Business is a great place for food and drinks with friends. It has a fun atmosphere and is surrounded by other restaurants and bars in Wicker Park. I'd for sure come again!

    Pickle backs!
    Thuy Dan T.

    Whiskey business has a nice patio rooftop for you to enjoy with an adjacent indoor bar if you'd like to sit inside. The staff is friendly and there's something at the top looking for an open table for you. There are servers throughout but if you sit inside the bar, you just walk up. If you'd like one of the bigger tables, I'd recommend calling ahead to make a reservation. When sitting in the patio is definitely gets hot under the sun! Not as many fans or misters and the umbrellas are a hit or miss. The frozen drinks are pretty sweet (too much for me). We ordered Jameson shots with pickle backs and the shots were plentiful but the pickle juice was so pretty small. We kept having to ask them to pour more. All in all, a positive experience and I would consider coming back when I'm in the area!

    Latrice A.

    Busy here on Thursday which we learned was ladies nite, hey cool I was with my gal pals I believe we Arrived at 6:00 p.m. close so there was no crowd or no wait to be seated and we were able to seat ourselves and the waiter who was very overwhelmed because he let us know that they were under staff but he did a great job he seemed like to Anticipate when we needed him eated him also I ordered a drink that I was not fond of and the and he swapped it out for me even though I took a couple of sips And we only went with appetizers which was the spinach dip and a quaso nachos It was nice casual vibe it was starting to get crowded as we left

    Mimosa Brunch
    Joneice B.

    Partied here on a Sunday morning with my friend who had reservations for brunch with her cousins. I didn't end up eating here because I had reservations at another location. I will say that they're mimosa deal seem like a really good bargain. I enjoyed my momosa which was made with Wyclif champagne or maybe that's Proseco not sure. My friend got some wings and those looked delicious and they also smell like they had the right level of spice. The outside roof deck had lots of space and a good amount of locations to take some cool pictures. I definitely will come back when I want some good wings and some whiskey.

    Inside bar area
    Elizabeth A.

    Came in for a quick drink while waiting for a dinner reservation nearby. The environment inside was really chill and welcoming. The drinks were well priced and yummy. We paid around $50 for 4 drinks and a shot. We tried the spicy mango margarita, paloma, mojito and espresso martini. All four drinks we recommended and would get again. There is also games to play like darts, skeeball, jumbo connect4 and jumbo jenga. The man serving us was also very nice and personable. Definitely looking forward to coming back and checking out the rooftop next time!

    Rie U.

    First things first, the rooftop patio is a nice little space for hanging out with friends. There are umbrellas so a little drizzle or sun won't ruin your visit. There are couches for bigger parties, and TVs all around if you're the kinda person who can't miss a game. The food was solid. Didn't blow my mind but also didn't underwhelm me. The chicken and waffles is a smaller dish, which turned out perfectly for me. Totally needed all the deep-fried foods! The Truffle Shuffle Fries were tasty and I'd get that one again! Lastly, 18% gratuity that's automatically added to your bill?? I'm sorry but that's kinda crappy. Also, the electronic billing system doesn't tell you that you've already had 18% added to your bill and it prompts to you add a tip. Wtf? That's some shady business practice imho.

    Rooftop patio
    Brian T.

    Gorgeous rooftop bar during the warm weather. And I believe during certain days they show specific movies. Prices for cocktails are about the usual and they offer bar food until late. Games typically first come first serve include giant connect four and giant Tetris among others

    Chesley M.

    It's always the rooftop for me. I'm a sucker for a good rooftop and Whiskey Business certainly passed the test. This was last summer and sorry it took me so long to review. The happy hour specials are great. It's nice to just chill on a hot summer day. Everyone who works here is simply amazing when it comes to hospitality. I've been here twice since last summer and unfortunately didn't get videos and these were all I had in my camera roll. This is a summer time Chi must. Great for a hangout spot after work or hanging with friends. They' even have rooftop movie night. There is plenty of (paid) street parking. Keep in mind I'm a Bourbon girl so the name alone made me want to check this spot out. Glad I did. Looking forward to our next outing ;).

    Ashten W.

    We hosted a collaboration event with Guaranteed Karma (a company that rewards volunteers for their altruism) and Whiskey Business on a summertime Chi Saturday afternoon. They were so fun to host an event with. The staff is super welcoming, hospitable, and friendly! After spending an hour street cleaning with the crew, we enjoyed cocktails and delicious shareable bites perfect to share with a large group! If you're visiting Chicago or live in the neighborhood, it's the perfect spot to create good memories with ya friends.

    Rooftop patio
    Alvin T.

    Don't get me wrong this place has a very fun and social atmosphere--we went on a Saturday afternoon and it was lively and had great things such as a large connect four board and Jenga. Come here for a good time and for drink, the food could be a bit better. The chicken and waffle board was mediocre at best. The chicken pieces were very small and did not have enough flavor and the waffles were more on the dry biscuit side rather than the fluffy side. We also ordered some mimosas that were pretty average. That being said, I think if you were to just enjoy the atmosphere here this place is definitely great!

    Rooftop

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    Thank you Chesley! We hope to see you again soon!

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    Alyssa, Thank you for an amazing review! Hope to see you again soon!

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    Page 1 of 11

    Ask the Community - Whiskey Business - Holly Jolly Pop-up!

    Are the bottomless mimosas at a specific time? If so when?

    Hi Dena! We do not offer bottomless brunch anymore, however, we have something even better now! It is called the F.O.M.O. - (F***ing Oversized Mimosa Option) Giant Mason Jar… Read more

    Hello do the haunted cabins have space heaters?

    They are enclosed and have space heaters

    Are the Wednesday movies outside on the rooftop?

    Weather permitting yes they are. Typically between November and March we only feature the movies indoors.

    Are children/people under 21 able to get in?

    I've never seen children in the establishment before. Might be best to call and double check.

    Is the rooftop open in the winter - even to hang in the cold or do they provide heaters?

    Hey Steph! We have curling courts up on the rooftop :) Check out our Facebook or Instagram for photos! Hope to see you soon!

    Is this establishment kid-friendly for Sat and Sunday brunch?

    Not particularly, it is more of an adult day drinking vibe. They have a DJ, however the music isn't all that loud. The rooftop is more mature and the brunch menu isn't kid friendly. However, personally I enjoy an adult vibe.

    Do you have to be 21 to get in?

    Most nights they have bouncers, but not in the AM for brunch.

    View All 9 Questions

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    The Berkshire room is the Acme hotel's speak easy, but man, the drinks were rough! My Hermosa was…read morehonestly one of the worst drinks I've ever had! It tasted like a 5 year old got into their parents' liquor cabinet and just randomly poured whatever cheap liquor was in there, and mixed it with water! The ambiance was nice. Lightly lit, and easy on the eyes, but our server was inattentive and unfriendly, which made the drink that much more unappealing! Hopefully you have better luck than me here!

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    This spot inside the aviary came highly recommended considering it is part of the Alinea group…read more Service was quick and we were told we could request for a bartenders choice cocktail if we provided some general guidelines. My first drink was average and full of ice - disappointing. I did talk to them and swap it out for a mezcal sour which turned out to be much better. They were understanding and accommodative and offered up an alternative drink as well. Overall service was good and cocktails were decent. The fanfare to book this spot and the very rigid booking policies made this seem like a much more exclusive and sought after spot. The drinks were good but not spectacular. A good spot for pre dinner drinks in that neighborhood.

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    I don't know, maybe I'm just a hater, but I've given Gretel a shot twice now and left disappointed…read moreboth times. It was mainly about the service. Disclaimer that both times we sat at the bar. So this has nothing to do with servers at the tables. It just felt cold and not at the level I would expect for the prices and reputation. For example, we ordered the smoked trout caesar salad once at the recommendation of a friend, and didn't love it. It was very, very fishy. Like not just the smoked trout itself, the dressing also tasted way heavier on the anchovies or something than we're used to. And we love caesars! We didn't say anything about it because it's literally in the name that it may be fishy. The issue was that it was so obvious we only took one bite that the bartender commented on it when he was clearing our plates. "Too fishy?" We confirmed. And then he took the full plate of food away that he himself had just agreed with wasn't great, and returned with our bill that still charged us $20 for a salad. I mean, it's fine. But it's just an example of the kind of service you get there. We were barely checked on, even when drinks were empty. Even when making eye contact. Even when we were obviously done eating for several minutes and the bartenders were staring at our plates.Even after asking for a check and watching conversations happen leisurely behind the bar while we sat there. I know sitting at the bar is a different style of service, but it ventured more into inattentive than spacious. The space is cool. The food is fine. It just doesn't make up for feeling like a burden when I'm paying $100+ for lunch for two.

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    Whiskey Business - Holly Jolly Pop-up! - whiskeybars - Updated May 2026

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