::ROOFTOP REVIEW At The Robey:: I don't care what city I'm in - from Rio to Radford ima find a rooftop regardless. My brother is tired and has a toddler. I'm child-free and perimenopausal. Somewhere betwixt the two of our sad state of affairs we found enough energy to go out on the town to see the city lights. Actually I insisted upon it and no matter what age we are, an older sister can always bully her younger brother into submission. As the internet is basically a bowl of chopped n screwed AI nonsense - I went to the only remaining search engine with integrity - Reddit. Query: "best rooftop bar in Chicago no douchebags don't piss me off Reddit?" And The Robey was the answer. Now mind you our 51st state, Canada, was on fire last week and air quality in Chicago was shot to hell. But we decided to SEND IT and go outside anyway. What a delight! It was precisely the vibe I wanted. Quiet, a likkle queer - I will not elaborate - good for friends and lovers. The tables have a low profile that makes scene watching intimate and accessible. Comfortable chairs, low candlelight, open walkways. Feeling chilly? The inside is quite lovely too. I can't speak for the weekend scene - mama is a smooth 46 and my days of Friday and Saturday night rooftops are far behind me. But a Sunday or a work night?? I'm in there. Other things I loved: - the drinks were fantastic!! Like we had already been at another bar (review incoming) where I exceeded my 2 drink max by 4 (mind your business) so I was down for "just one more" at Robey. Welp 3 additional drinks later... -excellent table service and recommendations - the grotto. I can't explain. -city lights. Air quality on -1000 and they still gave me all the feels. Imagine on a clear night?!!! Ugh anyway if you want a great view of the city without being in the building you're trying to look at this is the spot. Decent prices too - as in I woke up the next morning and wasn't disgusted at my card alerts lmao read more

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This is by far one of the nicest spots I've seen in Chicago with a lovely view of the city. Go here at sunset or just right before to catch the entire city in a golden hue. They have some great cocktails and a very interesting triangular shaped area to sit in. Cocktails were great but honestly this spot is perfect for a date night with lovely views of our favourite city. read more

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This is the place for a cocktail in Wicker Park. Amazing views of downtown in a small cozy cocktail lounge on the top floor of Robey Hotel. If you are looking for a nightcap after dinner or a drink to close out an weekday evening I would suggest this place. I went on a wed night at 10pm and it was pretty full but we got bar seats. It seems like a place where you have to take a shot and it might be full but if its not it is definitely worth it. read more

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Came here for the cocktails and views! So so pretty. The service was slightly slow, but fine if you're not in a hurry or anything. Cozy vibes. I had the secret garden cocktail, delish! read more

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Love the space and ambiance! Service was a bit slow, but the vibe was amazing! I highly recommend for a party of 4 or less. read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

The Up Room at The Robey is a comfy spot for a drink and a view. We were staying at The Robey and went to the Up Room to check it out. There was an event underway outside on one side, which limited outdoor seating. Our hostess took our order and told us she'd let us know when a space opened up outside. That was very kind of her. I ordered a Grotto Smash - Reyka Vodka, Blackberry, Mint, Lime. Oh my, it was tasty! I had a few more! They made NA versions of the same drink for Mark. How cool is that? We spend a lot of time outside taking pictures. I think we may have been outside when the server let us know there was a space for us to sit outside. Fabulous! It was a nice evening. read more

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This place was a perfect date spot to pop into after dinner and before a comedy show at the den. It is so dang cute and swanky feeling. The little private room outside is a fun touch for a group. LOVED my cocktail read more

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My friend brought us here as we visited Chicago and it was wonderful! It had beautiful views all around and the drinks were delicious. I definitely recommend coming here, especially if you are visiting the city. read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

Robey Rooftop: We came here for a private event and it was wonderful! Views: The views are beautiful. It is cool to be able to look at the city in a different angle and appreciate the beauty of it. Drinks: The espresso martini and skinny margarita was delicious. The bartenders working the event were so patient and very professional (even when they could have easily been very overwhelmed). Food: Their focaccia like bread, veggie sandwich, and hummus were a personal favorite. I can't wait to come back and try out the cafe and other parts of the hotel! read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

The UP Room is visually so stunning. Perfectly quiet, dimly lit, high up. Vibes are so great however their drinks were so bad. We had 2 matcha martinis and they were -1947393902/10 bad. Dirty martini was horrible also. Such a shame cuz the place is so pretty. read more

Up Room - Matcha martini - Cocktail Bars Near Me - Chicago, Illinois

New obsession, a must try if visiting Chicago or just need a place to hang with friends after a long day at work. It's welcoming, the drinks are fantastic. Staff are incredibly kind and the view is fabulous! read more

Up Room - Mezcal cocktail and Cabernet - Cocktail Bars Near Me - Chicago, Illinois

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this place is perfecttt. the best place to savor the summer sunset with near panoramic views!! make sure to come cute or the servers might out-dress you lol. the drinks are creative and not outrageously priced considering it (averaging $17). honey heights was exceptional and sweet, as was secret garden. great date or girls night spot but also makes for a swanky group or corporate event space. read more

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I would recommend this place solely on the view. This bar is such a cool spot to go to during the warmer months. The drinks were good and the service was nice. You are able to take the elevator directly to the top floor. The bar is not the biggest area, so I recommend coming early to get a seat outside to enjoy the view. read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

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So funny story, every time I am in the Wicker Park area, I make an attempt to walk-in to this place but was always unfortunate, however, for the first time on a Friday night, we got lucky and I could finally visit this cocktail bar! (with a large party?!) Up room was the final stop on our food and drinks crawl experience and we loved it! They do not have a lot of tables inside however they have a pretty huge patio. We also found out an enclosed space where our party could relax and enjoy good conversations. The enclosed space was heated so we could enjoy it even on a cold wintery night. My friend and I tried Chai me to the Moon and Sky High cocktails and they were amazing! I'll definitely come back to try more cocktails. The view is beautiful and you can see the entire Chicago skyline on a clear night! Overall, a nice cocktail bar you should check out if you are in the neighborhood. read more

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This staff is so unprofessional. My friend and I came here last night. When we were leaving the bar, the hostess ran up to me and told me I need to pay my tab. I was very confused because I literally paid my tab and spoke with the bartender a few mins ago so I told her this. She made me follow her back to the bar to check. At the bar she asked for my name to look up my tab and then she asked which bartender I closed out with. This made me even more confused because if you don't even know the name on the tab or the bartender how are you assuming that I didn't pay my tab?!!! This just indicated that you stopped me because I'm Black and assumed I didn't pay my tab. I pointed to the bartender and that bartender came up to me equally confused as to why I was back regarding my tab and he told the hostess yes she closed out already. The hostess just looks at me and goes "Okay you're good". I know people make mistakes and I was so nice about the situation until that point but the fact that she only said that and tried to brush it off without apologizing for chasing me down and wrongfully accusing me of not paying my tab is evil. I literally told her she needed to apologize to me for what she just accused me of and she immediately became defensive and tried to make up excuses. One of the other confused in a different way bartenders tried to interject in the conversation and side with the hostess which was also unprofessional because he didn't even see the part where she chased me down, wrongfully accused me, and made me walk back to the bar so why are you even defending her? The hostess ended up apologizing in the end but it is ridiculous that this situation even happened. She had absolutely no reason to stop me and accuse me. Also I want to add that when we spoke with the hostess at the beginning of the night to get two seats they told us it would be an hour wait which was fine so we asked to put our name down and they told us there'd be no point because they close soon. They told us we could check the outside seating. It was cold out so I asked if there were heaters outside and they said no. We went inside anyways to stand and get drinks and there were literally two seats at the bar so we sat there. We also went outside to take pictures outside and saw there were heaters outside!!! Why lie about that? It seems like they were just trying to turn people away. Please don't support this place. read more

After several failed attempts to get a table at the Up Room in the past, we finally got a table. The space is relatively small in terms of seating, but the patio is huge. There is also an enclosed seating space which very few know about. We tried the chai me to the moon and the Sky High cocktails, both of which were great. The service was fast and the server was attentive. The view is just breathtaking and was definitely the main highlight! They have an unobstructed view of the whole downtown skyline and it is a treat to the eyes. read more

Up Room - Chai me to the moon - Cocktail Bars Near Me - Chicago, Illinois

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Enjoyed after dinner drinks at Up Room recently. Up Room is a rooftop bar atop the Robey Hotel. It has a modern, sleek vibe and is surrounded by windows on 2 of its 3 sides. Service was very good. They allowed us to choose our table, and we chose indoors because it was so windy. I ordered a glass of wine (extensive wine list to choose from) and my daughter selected a cocktail that she enjoyed. The real draw is exploring the patio outside. It's 2 sides of a triangle with amazing views of downtown. Definitely a place for a photo op with your friends or family! read more

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13th Floor! The Up Room located in the Robey Hotel in the Wicker Park area. A Very cozy intimate and beautiful rooftop. Views from the rooftop were breathtaking! The nightlife in Chicago is something different I tell ya! Stopped in for drinks after a great dinner, decided to try out a cute rooftop! Perfect for the winter moments as they have a cute warming shack. They also have a dope rooftop pool that sits on the other side of the bar which is great for summer months. They also have a cute cocktail menu with plenty of options. Our server was great, he served us with grace. Check em out! read more

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Absolutely Amazing I wish I could stay up here all night the ambiance and the servers are just great I want to gatekeep but it's already been popular for a while now. read more

This is my second time visiting this super low key rustic/ vintage rooftop in Bucktown's downtown area. I say downtown lightly but it's still a whole vibe. Note, this low key rooftop is inside the Robey Hotel which in and of itself is hard to miss if you're not quite sure what you're looking for. The first time I attended was a summer Friday evening and it was popping. The drinks were delicious and the service was top tier even during rush-hour/ season. This past Thursday evening I have to say it was a different feel but I still enjoyed my experience. My neighbor and I chose to come here to catch up with a low key vibe. I ordered the neon nights and he ordered the Oaxacan on Broken Glass beverage. First rule, order both! Second, enjoy because these were quite tasty. For a $17.00/ piece drink, this definitely was worth it. I'd be sure to return. read more

Up Room - Neon Nights - Cocktail Bars Near Me - Chicago, Illinois

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Went up the gold escalators after dinner at Cafe Robey around 9:30-10pm ish on a Sunday without a reservation and we were seated right away. It was pretty empty when we were seated, but it steadily filled up as the night went on. This place has the most stunning view of the city skyline. Once you get your waters and drinks, you're able to get up and walk outside without your seat being taken. They have heat lamps outside too. The inside feels cozy and intimate with the dim lights and music. The music wasn't loud so it was easy to carry a conversation. You don't have to shout to be heard. Perfect date spot All the drinks were delicious and came out pretty quickly. Peach emoji and lucky 13 were sweet, almost candy like. Oaxacan has a fun, smokey element that you can keep or remove by taking out the smoked thyme. Old fashioned was a sweeter rendition of the classic drink. I'll definitely keep this place in mind for when I have out of town guests to show them a different view of Chicago skyline. read more

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I think this is hands down one of the best views of the city from this direction, and to be able to have drinks from up here in a beautiful setting makes it 10x better. The drinks are pretty much similar to what they have downstairs on the second floor, but I went with something else up here and it was great! There are two gender neutral bathrooms here and they are very clean as well. It would awesome to stay here at this hotel as guest! read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

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This cocktail bar is great, they have a lot of drink options and a wonderful view of the city, it's so beautiful. Highly recommend! read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

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Awesome views of the city!!! A roommate and I stopped by and loved the drinks and the gentleman who waited on us was super friendly and even made my drinks mocktails as I had to be sober. Would definitely stop by again! read more

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Such a great spot to enjoy crafting cocktails with an actual view of the city, 10/10, bartenders, servers and host team make me feel like home evrytime read more

Up Room - Options for mocktails, here is the sober sour a mix of Hibiscus, ginger and lemon - Cocktail Bars Near Me - Chicago, Illinois

Recently visited Chicago and Up Room. What's Up Room? Not much, but Up Room is a very nice bar that has an amazing view of the city, especially at night. It's a rooftop bar that is on the 20-something floor and has a great view into the tall buildings of the city. The food and drinks are also great. They have some very interesting specialty cocktails and some good food to snack on. I tried a spiced Oaxacan cocktail and their charcuterie board, which was a decent amount to share with 3-5 people. The ambiance and service was also really nice. It has a comforting and relaxing atmosphere as a small bar, and the servers were very personable and gave us recommendations on drinks. Overall, would highly recommend. read more

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The sunset and nighttime view of the city is the reason to come to this rooftop bar. The cocktails are decent, though I personally think the nearby The Violet Hour makes better drinks. Service was timely, and the staff were knowledgeable. The NA drinks were reasonably complex, in order to justify the similar price to alcoholic drinks. TLDR: come here for the view, especially in good weather in the summer. read more

One of my favorite cocktail joints in the city! It oozes a nice amount of sex appeal as it has an amazing view of the city from a 360 perspective. Downtown just looks stunning from this view! Sitting inside is nice as well. This place is located in The Robey Hotel on the very busy NW corner of North, Milwaukee & Damen. Service here is always on point as I've been here on dates and with friends and its always good! The drinks are of course very good! One standout cocktail is the Oaxacan On Broken Glass, which is a mezcal cocktail. I definitely recommend! The Robey Old Fashioned, Black Manhattan and The Purple Rain is very good as well! With all this said, you can purchase champagne, wine, beer and neat spirits if you choose...there is a good amount of options. Small bites are available as well. Vibe here is amazing as its a chill spot which is always up my alley! It's not a huge internal space but its pretty cozy especially for dates. Get here if you haven't been. read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

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This is the most beautiful place in Chicago! The view was immaculate! To see all of the city lights was perfect! The service was great. The waitress were helpful and nice! The drinks were alright, nothing too unique, and were a few oz. The price was pretty high, but it makes sense for the view you are getting. I'm not sure if i would come back. I think one time was good enough. read more

Up Room - Drinks - Cocktail Bars Near Me - Chicago, Illinois

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Easily one of the best cocktails I have had in the city!! The Oaxacan on Broken Glass is the only cocktail I have had that has gotten progressively better as you drink it. They light the rosemary garnish so the presentation as incredible, and you taste the spicy flavor changes to the smokiness of the rosemary as you drink it. Still thinking about it! Not to mention the views and the ambiance are fabulous; it's a very unique view of the city. The service was great too. Cant wait to go back!! read more

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WOW! This place has an absolutely stunning view! Service - 5/5 - Got seated immediately with no reservations. Our waiter was conscious of my partners bad knee and made sure our seats were accessible without us even asking. Nice, personable and friendly staff. Ambiance - 5/5 - LOVE! Inside had great lighting so you can see the gorgeous lights of the city. The bar was surrounded with glass and you're able to go outside on the terrace to take further pictures and admire the view. Drinks - 4/5 - We got the espresso martini and the oaxacan broken glass. Both were made well with quality ingredients at a great price point. Overall, a great place to grab a quick drink with an awesome view. Would love a romantic date night :) We'll be back here on our next trip! read more

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We took an Uber to get here and came right when they were closing, unbeknownst to us. So you can imagine our faces showed shock, sadness and disappointment. But Patrick was super cool and still let us in so we could see the views. Aaand he still let us order drinks! We were super happy we could stay. The view was lovely and Patrick was so cool. The inside is dark but romantic with table candles and very intimate. read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

NEVER have we had a bad experience here. Not once. We've been at least a dozen times since moving here. Indoor service, outdoor service, bar service. Always perfection. We love the little charcuterie boards here too. The cheeses, meats, nut mix is yummy, as are the olives! The cocktails are literally to die for. SO GOOD! AND they have those absolutely beautiful clear huge ice cubes! Gorgeous in an Old Fashioned! This lounge has very talented and skillful bartenders, who are literally so creative and artistic! It's a blast to go there and say, "Surprise me!" and then be served something incredible! The staff here are also SO friendly and helpful. And QUICK. We have never been left waiting. In the dozen or so times we have been there, we have had experiences with Audrey, Demetrio, Alice, Emma, Seth, Jesenia, and Managers Keke and Germaine. All absolute professionals. It's rare to find so many incredible people are in one place. I guess this is how you end up with "our favorite spot!" How do I know all their names? Because that is JUST HOW GOOD the experience is there. Worth remembering! Oh! Almost forgot, THE VIEW!! WOWOW!!! Take that view in! It's so worth it! read more

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Really cute spot to grab drinks with a view! I forget which drinks I got but they were good and fairly priced!

This place has one of the best views in the chi and the most amazing craft cocktails! I ordered a Penicillin (a drink even some experienced bartenders aren't familiar with) and the bartender Emma did an exceptional job making it. And to top it all off my server Alice was extremely sweet and accommodating. Whether you're a Chicago native or just visiting for vacation, I couldn't recommend this place more! read more

Up Room - Cocktail Bars Near Me - Chicago, Illinois

I saw an Instagram story of this place and had to check it out. Definitely did not disappoint. What a great spot! I went on a Wednesday night so there weren't too many people. We were seated right away. Everyone was really attentive and helpful. The views are amazing! Wow. I love seeing this side of Chicago. We were able to go outside and explore the 360 view of Chicago. The drinks were also amazing. There were $17+. I got the purple rain and the kiss like a rose. With just those two drinks, I was already feeling it. Great spot for a date night to talk over drinks. Definitely will come back here again read more

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The Up Room at the Robey Hotel located between Ukrainian Village and Bucktown, is this super hip, very nice, and popular rooftop bar serving some amazing cocktails. It was so busy this Friday night that we had to walk in sideways. Dark, old school we were afforded some of the best "people watching" we've had in the eleven months we've been living here in Chicago. My son and I had Wild Turkey 101 with a side of branch water The girls had The Roby Old Fashion made with Evan Williams Bonded 100 proof Bourbon and angostura, demerra and orange that they loved We walked outside on this blistering cold night to catch a 360° view of this incredible city, with Damon & Milwaukee avenues lit up to show off its "Holiday Lights". It was quite a spectacle. I really want to come back here in the summer and sit outside and see Chicago in an opposite season - and I will. read more

What a cool bar! This place is swanky. It's has very dim lighting. Very chill and relaxed atmosphere. You can step outside and you are high enough to see the city from the balcony! Service was fine. It was quick and friendly enough. Perfect for this type of place. They have a full bar, with limited brands. Many creative and custom drinks. I had a lemon drop martini that was perfectly sweet and sour. I also had an espresso martini that was really yummy, but a little sweet. Drinks can be pricey, but so worth it for the experience! read more

We checked the website before going which said they were open until 1am. Arrived a little before 11 and they told me the wait for 3 people would 45 minutes to 1 hour. I agreed and added my name to the waitlist then waited around. I got a text at 11:06 that said the estimated wait time was 1 hour. At 12:13, I still had not gotten the text, so we went to ask where we were in line. They said that they already did last call at 12 and that there was nothing they could do for us. It was especially frustrating because they didn't tell us anything about a last call or when we put our name down; just said "yeah no problem" and let us wait. Seems to me like a pretty big caveat for arriving at that time. Had they said they do last call at 12 we would not have waited, but there was absolutely no mention of that at all. So basically we waited around for nothing and the staff made us feel like idiots for having done so. Just be upfront about these things. It's not that hard... read more

Our group had a surprise engagement party for our friends here and we rented the corner space through coordination by Jillian from the Robey team. They were super flexible with our budget and allowed us to pick from a number of stationed appetizers and have a bar tab. Once we reached our minimum for the tab, they switched It to a cash bar! The coordination with Jillian's team was impecable and we cannot recommend her or this place enough for your next private gathering ! read more