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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
    Casual
    Moderate noise
    Happy hour specials

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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.

    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.

    Frozé

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    5 years ago

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    6 years ago

    Whiskey business is amazing! I love and everyone should go and specially ask for David as he treated us wonderful!!

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    6 years ago

    The chicken sliders and the pretzel bites were gross. The waitress was rude and unwelcoming.

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    Page 4 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… 

    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 Franklin Room

    The Franklin Room

    4.3
    (635 reviews)
    2.0 mi
    $$$

    The Franklin Room is one of our favorite restaurants in the city--and we're lucky enough to live…read morejust a few minutes' walk away! From the ambiance to the food to the service, you can tell they hold themselves to a high standard, and they consistently deliver. We love coming here for date nights and even celebrated our anniversary here. It's also one of our favorite places to bring friends and family when they visit. Great food, wonderful atmosphere, and consistently excellent service. A true hidden gem in Chicago!

    The vibes were nice. Lighting wasn't too bright, a dressier atmosphere, and definitely felt like a…read moregood spot for drinks and dinner. Service was fine. Our server was nice and water refills came at the right times. The burger was honestly pretty mid. It tasted fine, but our server said it was one of the best burgers in Chicago and I definitely wouldn't agree. 5/10. The salmon was tender and had a really interesting crust. It wasn't charred like I expected, almost had a rubbery texture, but I actually enjoyed it. The lemony miso sauce was delicious, the pickled cucumbers added a nice crunch. 7.5/10. The prime bone-in ribeye was fine. Good flavor, but nothing really stood out about it. 6.5/10. Dessert was the highlight of the meal. The chocolate crunch dessert was sooo good. Loved the marshmallow pieces and all the different textures from the crunchy mousse. 8/10. The salted caramel gelato had a great texture, but it was way too sweet for me. It tasted more like straight sugar than salted caramel. 6/10. Overall, a solid last-minute date night spot with good vibes, but the chocolate crunch dessert was definitely the standout.

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    The Berkshire Room

    The Berkshire Room

    4.1
    (475 reviews)
    2.5 mi
    $$

    The Berkshire Room is one of my favorite speakeasies in Chicago. While they offer a fantastic…read morecocktail menu and a full bar, I almost always order The Dealer's Choice. You simply choose your preferred spirit, flavor profile, and glassware, then let the mixologist create something just for you. It's one of my favorite cocktail experiences in the city, and they've never steered me wrong. What I especially appreciate is how knowledgeable the bartenders are. They're always happy to offer recommendations if you're unsure what to order, but they're equally excited to create something completely unique if you're feeling adventurous. Watching them craft each drink is part of the experience. I've even hosted a birthday gathering here in their private side room, where we enjoyed charcuterie boards alongside our cocktails. If you're just stopping in for drinks, though, I'd recommend grabbing dinner beforehand, as the food offerings are fairly limited. More often than not though, you'll find me sitting right at the bar. I love watching the bartenders showcase their craft and chatting with them about the incredible selection of spirits they have on hand. It's a great spot for anyone who genuinely appreciates well-made cocktails and the artistry behind them. I'm also a member of their loyalty program, which is well worth joining. It can be used at The Berkshire Room as well as several other excellent restaurants, making it an easy way to earn rewards while exploring some great dining spots around the city. Whether you're a cocktail enthusiast or simply looking for a sophisticated place to unwind, The Berkshire Room consistently delivers. I'll definitely be back for another Dealer's Choice soon! #YelpEliteSquad

    I came here in 2023 and remember constantly remembering how good the cocktails were so decided to…read morestop back in and they were just as good as I remember! I came the night I got engaged so we decided to go on our anniversary as like a cute little celebration after dinner. The service is always amazing and the interior is very chill, great music. They can make anything you ask for but their cocktail list is extensive and has so much to choose from! Highly recommend.

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    Trust the mixologist - your Dealer's Choice cocktail is in good hands
    Trust the mixologist - your Dealer's Choice cocktail is in good hands
    Host your next event at this speakeasy cocktail and whiskey bar in River North!
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    The Office

    The Office

    4.3
    (320 reviews)
    1.7 mi
    $$$$

    The Office is a nice speakeasy! I had wanted to get a floral drink at the restaurant upstairs…read morecalled "the Aviary" but they were actually totally full, whereas the speakeasy wasn't. I sat at the bar downstairs and can confirm the place has a classic speakeasy feel -- the the basement of a place behind a locked door, very dark inside with mood lighting/glass cases and leather chairs/couches around small low tables. It's definitely a great date spot! I took off a star because it's pricey -- I got the "milk punch" on their classic cocktail menu which was $25 and is pretty small, but it's a nice drink and tasted very much like a milk punch drink I got at a speakeasy back home (in Austin, TX). The bartenders were super nice and provided excellent service, no complaints there! The bathrooms were also immaculate. Overall, this is a very nice speakeasy! I've been to many in my day and the ambiance is definitely on par with the best, but I gotta say some other unique ingredients (ideally more floral options!) would really take their menu up a notch! Nevertheless, I would def rec a visit to those visiting Chicago, and would go again even just for vibes :)

    This is a speak easy below the aviary. We sat at the bar and were the only ones there so got to…read morechat with the bar tenders. They were super nice. It's got a speak easy library vibe. Maybe seats like 20? The food was surprisingly great. They have a raviolo that is like $20 for one but it was the best thing I've ever put in my mouth. I wish I could have a whole plate of them. Drinks were also great.

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    Twas a combination of a black manhattan & a vieux carré  Delicious
    Twas a combination of a black manhattan & a vieux carré Delicious
    Basque cheesecake was delicious
    Basque cheesecake was delicious
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    Longman & Eagle

    Longman & Eagle

    4.1
    (2.6k reviews)
    2.4 mi
    $$

    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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    Happy 2024 everyone!! - Bahr
    Happy 2024 everyone!! - Bahr
    Smash Burger & Fries
    Smash Burger & Fries
    Sport Pepper Vesper: Letherbee Gin, White Dog Mash #1, Cocchi Americano, Sport Pepper

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    Sport Pepper Vesper: Letherbee Gin, White Dog Mash #1, Cocchi Americano, Sport Pepper
    Gretel

    Gretel

    4.5
    (476 reviews)
    1.6 mi
    $$

    This is my third time at Gretel and the food was even better than I remembered it! We came around…read more5pm on a Sunday and there was only about a 10 minute wait. They sat us downstairs. I had only sat upstairs at the bar and outside, so I was happy we were able to see the downstairs. It's very intimate down there with only a few tables, while the upstairs is a lot more of a lively bar atmosphere. Service was good and fast. They are known for their burger but I am not a huge burger fan. Their other food is amazing though! Even my boyfriend who loves burgers agreed that the chicken sandwich was one of the best and maybe even better than the burger. Definitely get the mac & cheese, chicken sandwich, and french onion soup. The french onion soup was super cheesy and the mac & cheese was so creamy and perfect. Typically I don't like bacon in mac & cheese, but I love that they don't overdo it here where it overpowers the entire dish. It was only some tiny pieces of bacon just for the flavor.

    Came for the burger, but stayed for the drinks. Maybe I chose a bad night, but I thought the burger…read morewas disappointing based on its hype and Gretel's reputation. Hands down, the saltiest burger I ever had in Chicago. At least, they were generous with the fries. Laidback vibes and cool space, I would come back to try the other cocktails on the menu with friends.

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    Flowers
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    Outstanding butter & brine oysters from portsmouth maine
    Outstanding butter & brine oysters from portsmouth maine
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    Whiskey Business - Holly Jolly Pop-up! - whiskeybars - Updated August 2026

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