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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?
Casual
Moderate noise
DJ
Good for dancing

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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

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.

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 ;).

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.

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4.1(477 reviews)
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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 made a reservation at The Berkshire Room during the first week of October for my wife's birthday…read morecelebration on Halloween weekend. We were really looking forward to the evening and had planned part of her birthday around this reservation. Now, just 10 days before our reservation, I receive a generic text message informing me that they have booked a private event and will no longer be honoring our reservation. No phone call, no personal email, no attempt to help find an alternative or make things right. Just a text saying they can't accommodate us and would be happy to reschedule for another date. I completely understand that things change and businesses have opportunities for private events. However, accepting reservations weeks in advance and then canceling them less than two weeks before a major holiday weekend is incredibly poor customer service. What makes this even more frustrating is that it's Halloween weekend in Chicago, and most comparable restaurants and cocktail bars are already fully booked. Finding a replacement this close to the date is nearly impossible. The most disappointing part isn't even the cancellation itself. It's the complete lack of consideration for customers who made plans in good faith and trusted that their reservations would be honored. If you're planning a special occasion around a reservation at The Berkshire Room, I'd strongly recommend having a backup plan. Apparently, a confirmed reservation doesn't mean much if a better opportunity comes along. Very disappointing experience, especially from an establishment that positions itself as an upscale cocktail destination.

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Trust the mixologist - your Dealer's Choice cocktail is in good hands

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4.4(324 reviews)
1.7 mi•Fulton Market, West Loop, Near West Side
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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!

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 :)

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Twas a combination of a black manhattan & a vieux carré Delicious

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Longman & Eagle - Summer Squash Salad (v): Zucchini Bread, Chèvre, Peas, Pickled Kholrabi Vinaigrette, Pecans

Longman & Eagle

4.1(2.6k reviews)
2.4 mi•Logan Square
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We came here because a friend recommended it. We stopped on a Sunday for brunch. I'm giving it a…read morefive. The only minor negative was the lack of signage outside. We didn't know if we were going to the right place. That being said. The hostess was kind. We chose to sit at the bar. The bartender was great. There were a few back there and all kind, knowledgeable and helpful. The food was outstanding. I had the Turkish eggs and we shared the potatoes. They looked like big tater tots. But 100000% better. And my hubbs got the smash burger. Just so impressed. I truly. Loved every bite. And to make a big deal about the food we had.......i am because it was that great. Coffee was great and so were the other bevy's we had. We will def be back and try the dinner menu(great tip from the bartenders--)

Bottom Line: Though overall very decent, not a place I'd make a special return trip to but it is a…read morepub-upscaled option (pricey one) if you're in the neighborhood and will provide at least a quality experience. Call and up your credit limit though. I can't help but feel there is somewhat of mismatch here. A mismatch between the talent in the kitchen and an ordinary corner pub--a nice corner pub in the historic Logan Square neighborhood but nothing that makes it necessarily standout for a City pub--and that's ok for a pub. It's a pub. It presents with lots of warm, woody tones making you want to settle in with a nice Maraska and stay a while with good conversation. Overall the libation selection is varied and sophisticated. I do love that they offer good Sherry, Port, and Madeira which is very rare. Most places you'll get a blank stare if you ask for Madeira. The wine selections are internationally representative but highly overpriced and under poured. The brew selection is the least impressive of the libation lineup and is IPA, golden lageresque heavy with an obligatory stout and a couple of seasonal Oktobers (It seems modern American palettes demand their beer to be only golden and hop-forward.) The dinner/dining environment is split in two with bar area tables and a back dining area. The place has a long history as some type of bar typically found on almost every corner back in the day. The spaces are intimate and dimly but warmly candle-lit. Where this place really excels though is in its gastroness. We ate tapas style (everything is shared). They offer quite an array of original, chef-level creations that, though a bit pretentious, are quite enjoyable--just don't look at the price--just enjoy. Actually read the ingredients though so you know what you're getting not just thinking you know what you're getting. Ask questions. Nevertheless bravo for the originality and creativeness. I'm just not sure this (Michelin) two-star level food experience belongs paired with a nice but regular ole' pub (and that's ok) versus its own venue, but hey, they're the ones taking the risk. I would have been supremely happy with a (Michelin) two-star, pub burger (non-smashed), superbly made, medium rare, walked through the garden, with Comté (cheese), a slab of Canadian bacon, a sunny side up (chicken) egg on top with hand cut pommes frites (fries), salade de chou (coleslaw), and a nice Porter (Porter). I still would've given four stars, potentially even five. I will say that the opportunity to rent a room upstairs is evocative of euro-style boutique or old school road houses and adds an another level of interest. I'm just not sure I'd want to stay there but I feel that's separate and aside from the gastropub discussion. Nevertheless, I don't think you will likely go wrong here unless you got really bad service, just hate the sophisticated take on pub food, or are just insulted by the prices. If you're nearby give it a try to form your own opinion.

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Longman & Eagle - Bar area

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Longman & Eagle - Smash Burger & Fries

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

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