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    Whiskey Business - Holly Jolly Pop-up!

    3.4 (436 reviews)

    Whiskey Business - Holly Jolly Pop-up! Photos

    WHISKEY BUSINESS - HOLLY JOLLY POP-UP! ATMOSPHERE

    What's the vibe?
    DJ
    Moderate noise
    Casual
    Happy hour specials

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

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    Reviews With Photos

    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.

    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!

    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

    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.

    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.

    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!

    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
    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 ;).

    Rooftop
    Nick S.

    First time here in the spring on the rooftop. Nice vibe and the staff new what they were doing. Quinn was amazing she new her stuff amd was super friendly.

    Lana T.

    OVERALL: As instagrammable as you think it will be, but it's not just looks! The food, drinks, and overall service make this place a winner. ATMOSPHERE: I mean, I had to start with this one right. A fun rooftop in Wicker Park with fun colorful decor and string lights. They even had a giant inflatable unicorn. They play upbeat pop music that makes you want to dance in your seat. Such fun vibes! DRINKS: They have so many classic drinks like mojitos, old fashions, you name it but our favorites were the (what we called) an adult capri sun and the magic 8 ball shots. The magic 8 ball shots were mystery shots and as you can imagine, you shook a magic 8 ball to figure out your shot. Some options lead to dares and a reroll! FOOD: We ordered the chicken sliders, steak burrito bowl, and Mac and cheese. For a place that we thought might be all looks, typically I don't expect the best BUT this food was absolutely delicious. I would absolutely eat all of these things again. PRICE: I thought the prices here were quite affordable. $10 for Mac and cheese, $8 for the base burrito bowl (we added a protein for $5), and the chicken sliders were $14 for 3 sliders. Drinks ranged from $10-$15. The magic 8 ball shots were $8 each but some of us got some good liquor like Patron. The odds were in our favor that night! SERVICE: Our waitress was extremely attentive and kind. She was super fun to hang out with and encouraged us to video our magic 8 ball shot experience. 10/10 RECOMMEND!

    Frozé

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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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    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… 

    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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    A small group of us came in on a weeknight for after dinner cocktails... The venue is interesting,…read moresomewhat dim and vibrant at the same time. Definitely has a cool, fun vibe. Cocktails are ok... I say that because we ordered something that wasn't too off the wall which involved ginger simple syrup and they couldn't make it - odd for a truly craft cocktail joint. So, they're more mainstream with their cocktails. Service was just ok as well, not the best, but somewhat friendly. Overall - it's worth checking out, even if only for the venue.

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    Stopped by The Office last weekend after dinner, and what an experience! This intimate speakeasy…read moreis tucked away in the basement of The Aviary and only holds about 21 people, so it definitely has that exclusive, hidden gem feel. Reservations are $50 per person, but that amount goes toward your bill. And honestly, the drink options go way beyond the menu. I tried a daiquiri, a green tea shot, and a coffee inspired cocktail. Everything was unique, and they have an impressive collection of rare and hard to find spirits. The bartenders were extremely nice, knowledgeable, and informative, which made the experience even better. We also tried the cheesecake, which was a nice addition. The music was mellow but still gave the room a vibe. The atmosphere is intimate, cozy, and definitely feels like a place you go for the experience, not just a drink. Street parking is available. Definitely a fun spot to add to your Chicago night out!

    After my birthday dinner, my friends and I went to The Office, the intimate speakeasy in Fulton…read moreMarket, and it was such a great experience! The atmosphere is beautiful, cozy, and intimate, which made it perfect for continuing my birthday celebration. Our bartender was incredibly attentive, kind, and welcoming, and the drinks were absolutely delicious. We made a reservation and paid a deposit in advance, which was applied toward our final bill. I really appreciated how seamless everything was. They even surprised me with a little birthday treat and a candle, which was such a thoughtful touch and made me feel celebrated. We had a wonderful time from beginning to end. Great drinks, great service, and an amazing vibe. I would absolutely recommend The Office for an after-dinner experience, a pre-dinner cocktail, date night, or a special celebration. I will definitely be back!

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    What a wonderful meal! I went here as a party of 4 on a Friday night at 11:30. Who knew I could…read moreget amazing food this late at night? The pretzel, bone marrow, calf's liver, and chicken (with Miller High Life gel!!!) were wonderful. The drinks were well crafted and delicious. I will go back in an instant!

    It's been a "longman" standing joke with our family that we haven't been here yet, although we live…read more3 blocks away. For one, we are 2/3 vegetarian, and they had a reputation of being a bone eating, not vegetarian restaurant. Secondly, I use to frequent this location when it was "Winds" , a live music bar, and I'm a musician and advocate of live music. I even came here when it was "Smoke" dive bar previous to that. Thirdly, L&E also had a reputation of being a hipster hangout. I was pleasantly surprised how fantastic the NICHOLS FARM SUMMER SQUASH (V) Grilled & Shaved Baby Squash, Hari Chutney Vinaigrette, Coconut Curry Sauce, Zucchini Fritter, Garlic Labneh, with Spiced Pepitas was! Exceptional presentation and superbly delicious! My wife throughly enjoyed her smash burger, and I was pleased the fries were not fried in animal fat. Our dining neighbor that evening swore that they make the best vegetarian burger in the city. Prices were reasonable. Our server was very friendly, and Informative. He informed us the new chef, "she is more plant based." Nice beer menu selection of craft drafts and bottles, and local options, including up the street Hopewell brewery. Great ginger beer. We've always been interested in eating al fresco on Schubert, as we've passed it hundreds of times. We've finally broken the ice, and we will be back soon, and I can't wait to try the vegetarian Smashburger!

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

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