Has to possibly be the best South Side rooftop, with an inside and outside bar. It's been a long time favorite for watching sports and hanging out. Reggie's is best known as the sports bar near the McCormick Center station. For those wanting a dive bar experience, the lower part is pretty cool. The rooftop is where it's at though, so make your way to the upstairs. Back in the day they used to have more specials that brought people in on weekdays at the upstairs bar. It unfortunately doesn't have most of these anymore, and also doesn't seem to have as large as crowds. The last time here there were only a few others on the rooftop. A good thing about that was service was fast. The prices are unfortunately what have increased. It's about $10 for Long Island iced teas, which used to be cheap. These were still pretty strong though. It's about $9 for shareable bites. We got the Hummus. It came with quite a lot to dip. There was a generous amount of pita slices and vegetables. Atmosphere here still is pretty cool. There's a pool table and they still play hip music. Good to use the bathroom before. It's pretty gross, especially the one on the rooftop. The weather can play a part too, as the rain gets in everywhere, including on those at the pool table. read more

Reggie's Trainwreck Rooftop Deck - Outside - Bars Near Me - Chicago, Illinois

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Loud but good service. Mixed crowd. Food was hot and the shrimp platter was good. Burger was NOT good. Drinks were strong and staff was kind. read more

Reggie's Trainwreck Rooftop Deck - Bars Near Me - Chicago, Illinois

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Went there after having been in Chinatown and the teen wanted some different options for dinner. We sat on the rooftop and it was great. There was a pool table, basketball net and a shower, assuming in case you are overheated. We saw a couple of the marathon runners use it. The food was great. When I saw people get an order of like 30 wings knew that was the way to go. Our server was excellent and she was spread pretty thin as she was covering a lot of tables. read more

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Love atmosphere in this restaurant is definitely a vibe, pet friendly have fun shooting pool up on the rooftop where you can shoot hoop up there read more

Love the vibes here! The food was solid and good enough to keep me coming back. We have a salad, wings and a burger. This is a casual laid back rooftop restaurant bar with music. Just a note the rooftop is one floor up so there no skyline views but it's still cool. The best part of this place is that you can see the train drive past. We really enjoyed this restaurant and it was walking distance to the Hilton Garden hotel we were staying. read more

Both the waitress on the first floor and the young man bartending on the rooftop were extremely rude. Belligerent when answering questions and double charging for a vodka and lemonade with an additional shot. We were the only customers in the restaurant and I was shocked at how rude they were. We left after one round of drinks deciding to eat (anywhere but there) at Il Cucina a few blocks away. Granted we were not your typical young patrons, but this is a very bad look for this place ! read more

This place is awesome. Went to the rooftop part with 3 friends and the bartender was extremely accommodating. She's either a great actor or she was genuinely interested in talking to us. Either way 10/10 service. The drinks were great. She made a peanut butter and jelly drink for me that I'd never had before. Everyone sitting there was nice too. Chatty and willing to give us recommendations. Music was great too. read more

Visited my friend in Chicago and she said we had to try the wings. I could see how this place would be awesome in the summertime but it was not as cool on a 10 degree February night. It was super packed so we had to play musical chairs until we could scoot close enough to a table. For how busy it was, the service was super quick. We got drinks right away and the food took longer but it wasn't too bad of a wait. It's right on top of the L line which came by every few minutes so it felt like an authentic Chicago experience. read more

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We went on a Friday night for dinner and a couple beers. The atmosphere was great, and the music was awesome (though a bit on the loud side, if you are sensitive to noises). They had a good selection of beers, and the burgers were delicious. However, our server was inattentive for the first 45 minutes after we placed our order with her. We received our first round of drinks, and then nothing for 45 minutes. Finally, I had to go find her and ask if we could order a second round, and I believe that's when she realized that she never put in our food order. Our food came out about 20 minutes later. Ultimately, she ended up taking a percentage off the bill, which we did appreciate. The bathroom was kind of gross, so if you can hold it, I'd avoid using the bathroom on the rooftop. My fiancé said the bathroom on the first floor (part of the downstairs bar) was clean and in good shape, so that's an option too. Overall, I'd give it another go if we have a different waitress due to the ambience and food. Other tables with different servers seemed to have a much different experience than us! read more

My last time coming here. They don't care about black women being patrons or coming here and having complaints about their service. They pretend you are not important if you are a black woman. They paint you as being "difficult" even if you tip. I will never come here again. I just wanted fair and normal service and they ignored me. Not ever coming here again. IF YOU ARE BLACK DO NOT COME HERE!!! read more

This place is fun! I would recommend going to the rooftop for sure. They have a little basketball shoot-out. My friends and I got the frozen margarita, and it was super refreshing. I would say that the drink could have more alcohol, but nonetheless, it was good! The place was so cool. We got a free ride through their colorful (possibly sketchy-looking, but it's not) bus to the White Sox game, which was a plus! Overall, good vibes! read more

Sweet venue and great dive bar. Free pool table was awesome on the rooftop. Good times to be had here.

Come for the music, atmosphere, and drinks. The food is sub par but does the job. The wings are pretty good. The burgers are nothing extraordinary. The rooftop is set up for winter & is warm. Amazing service. read more

Reggie's Trainwreck Rooftop Deck - the outdoor dining area - Bars Near Me - Chicago, Illinois

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Listen this place doesn't look like much from the outside, or from the inside. BUT, best wings I have ever had, hands down! My friend had been raving about how crispy, but and juicy the wings from here are. This place definitely did not disappoint. They mix Buffalo and bbq and it is sooo good. I sat on the rooftop part in the winter, it was pretty cold but the entire place was packed due to a rock concert going on dow stairs. I will definitely be coming back here in the summer time to enjoy their rooftop and some more wings. read more

Love it. Grimy, loud, and delicious. Quite possible the best wings I have ever eaten. Well done.

Rooftop chillin'! This rock n' roll bar is a loud place to get some cheap beers and watch some TV while jammin' out. Roof tops are a great place to drink in Chi-town, and this is a fun roof top to do it on. Their rooftop is up on maybe the third or fourth floor of a big ol brick building. The rooftop has a bunch of bartenders, big screen TVs, and for some reason, an outdoor shower. Maybe they're optimistic about what kind of action they're gonna see. In my experience, it's often a bit cold to be showering on a rooftop. The bartenders are friendly here, with a decent selection of local beers and macro brews. They have big screen TVs showing sports, but when I went the sound was off and the music was on. They have pool tables and lots of outdoor seating, some of which are around places to keep warm. Downstairs, they have rock bands, with some actual real bands I'd heard of performing around there. Nice! They serve food here. It's greasy bar food- burgers and wings. I'm not sure where they're getting the trainwreck part of the bar around here. The rooftop does overlook the elevated train tracks of the L. When the trains whiz by, it feels like a real scene here in the South loop! read more

Very cool pace with great outdoor seating. Very casual with outdoor rooftop seating overlooking the train tracks. Just had drinks which were good. Food looked like standard bar food. read more

I'm was happy to find a place operating during COVID -19. Rooftop has easy parking and was comfortable to be outdoors on the rooftop with the weather. read more

I'm shocked to see so many low stars ! However you have to have personality up here . It's not much waitress covers so I a little hey y'all my food isn't here yet won't be rude lol the wings are my favorite ! I hate they super big but they are good . The quesadilla are good too . Drink are reasonably priced ! The area is fun and able to laugh and engage read more

Always a great time! Great food and reasonably priced drinks! I would highly recommend for a night out on the town with friends. If you're ever in need of something to do, or somewhere to be, this place offers all that you'd expect from a lively rooftop experience. read more

I was overwhelmed with hospitality by Emily the bartender. Felt like I was a regular who's been coming here 20 years. I love dive bars so much and this was perfect. Great music and Emily was very knowledgeable about the area and her drink recommendations. Didn't dine but the guests around had wonderful looking food. Will be back every time I'm in Chicago. The world needs more bars like Reggie's and more bartenders like Emily. read more

Reggie's Trainwreck Rooftop Deck - bar area - Bars Near Me - Chicago, Illinois

Fun hangout. Totally chill. Lots of seating. Music was fun, little loud for a decent conversation. Food was sooooooo good. We had wings, fries and onion rings. Service was a little slow to acknowledge us but after we got our order in service was fine. Drinks were strong and good. My one margarita should have been enough but of course I had several. Fun times. Liked the atmosphere. *Restroom upstairs near the bar was a Trainwreck! I didn't even want to wash my hands. :( Hopefully that was a one time thing. * read more

Reggie's Trainwreck Rooftop Deck - Bars Near Me - Chicago, Illinois

Loved this place. Laid back rooftop bar with good drinks and excellent chicken wings (had to try them because literally EVERYONE ordered them while we were there) soooo good. Was within walking distance to hotel which was a plus. We will definitely visit again. read more

Reggie's Trainwreck Rooftop Deck - All Day IPA - Bars Near Me - Chicago, Illinois

Reggie's was a regular hang out spot due to the fact that I live right next to it, however, after yesterday nights service I will probably never come back! The waitress working the back tables was so rude and non attentive. I left a 20$ bill on a 10$ tab because I wanted to get the hell out of there ASAP! I understand it's a bar, but at least come over and ask if we wanted food! I think she may have had a personal problem with me or something considering she was attentive to all her other tables. Probably need to work on etiquette. Also, when I asked to speak to the owner or manager the door boy was not helpful so I'm taking to Yelp to make sure people avoid this establishment if you want poor waitress service! read more

This is a cool place to go and just chill and on top of that they have some good food. Since they don't have a children's menu we ordered my grand daughter a hot dog. I can still taste my grand daughter's hot dog in my mouth...Oh this isn't one of those thin finger looking hot dogs but it actually filled up the bun. OMG, they know what a real Hot Dog is, I mean it was thick and it was flavorful and once everyone took a pinch of my Grand baby's Hot Dog she was guarding it with her dear life...lol She is only 3 but she gripped her hot dog with both hands and gave all of us the side eye like no one else better touch my Hot Dog!!! I can't wait to go back and order my own Hot Dog...lol I have been here about 5 times now and I have not been disappointed yet!!! The Burgers are clearly cooked fresh and the wings, whew they make you want to order more they are so goooooooood!!! I also liked the the fact that when they made a mistake with the amount of pieces of chicken they gave us that they were apologetic and sent up an extra wing!! If you want more than the small cup they give you of Ranch Dressing remember that is extra! I would say as a side note if you have a Resturant.com coupon that your drinks will be full price and that was a shock to us, as a courtsey after we spent well over 150.00 dollars for the group you would think they would have given us our two drinks for the special price but they didn't so now I know don't order the drinks unless I want to pay full price. I don't know how it works with Groupon but I do know on their Half Price Sandwich day you can not use your Groupon so it ended up being cheaper for us to use our Groupon at another time. Our last visit we ate up at the rooftop for the first time it was so nice and with the group of us it made it even more fun especially with their outdoor shower...fun, basketball hoop and just the wait staff and other customers... I would tell anyone if you want a great burger go to Reggie's!!! read more

Summers in Chicago are fantastic and spending a day or night on Reggie's rooftop is definitely something you should consider. It's got a kind of CBGB kind of vibe to it, as others have mentioned, and it is a dive bar but we enjoyed ourselves. They have a pool table, a shower, and a basketball hoop (almost like the kind you see at an arcade). Service wasn't a problem, but we sat at the bar, so that might have helped. We didn't try the food, but it all sounded great. We'll definitely be back when we venture down to Chinatown again! read more

Great food, fun atmosphere. the staff aren't the best, but I think that is part of the appeal. Very fun neighborhood spot for everything from brunch to pre game drinks (Go sox!) to late night partying! read more

Just what I needed after a long day of traveling. Pretty relaxed. Low key and fun. Night life is low key and fun.

Really Cool Rooftop! Totally came her on a whim and it had an awesome island feel. Even the guy who checked ids was friendly. The service however for food was seriously bad. When i first walked in I heard some guy yelling at the waitress" NO! I want to see your manager's manager". I didn't understand until I ordered my food and it took about 45 mins for 8 wings. I would be back to drink, but not to eat. read more

-My first time at this rooftop deck and I'm a fan! This is a perfect place to grab a drink or a bite to eat on a nice Chicago day. The rooftop has a great relaxed atmosphere with outdoor bench-style seating. The rooftop is pretty big and has a lot of space. They have a couple of TVs by the bar. There's also pool and a basketball hoop that you can use at anytime! Just be careful if you're not the best shot, the hoop basically overlooks the side of the building! Parking was pretty easy to find. -Food that I got was pretty good. I got the chorizo burger (1/2 off burgers on Thursdays when you buy a drink). The chorizo patty was flavorful and a great surprise. The burger came with a side of a peppery sauce, which by itself doesn't have much taste but goes well with the flavorful chorizo. Fries were very tasty with the burger. The only let down was that egg I got with the burger was overcooked. There are other daily food specials and I'll definitely try some of those. -Service was good. It wasn't too busy when I went with a group of 5 but the waitress was quick and responsive. The food came out fast and I never found myself thinking, "Where is my food?" A great sign. -All in all, a great atmosphere in the South side of Chicago with tasty food. read more

Reggie's Trainwreck Rooftop Deck - Basketball hoop on the roof! - Bars Near Me - Chicago, Illinois

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I've been coming to Reggie's for years. Pre-covid there were many specials that happened on different days but upon reopening doesn't seem like they have any. Patios still great tho! Love the basketball rim and pool table options. Plenty of space no matter what your group size is. read more

Just Awesome. -Outside Raised Deck -Cool Of Showers -Awesome Bartenders -Stiff Drinks -BasketBall Hoop -Plenty Of T.V's -Cigs Available Downstairs -Great Lunch Specials -$$$ -Drinks Can Be Pricey Due to The Amazing Chicago Afternoons & Evenings. read more

Reggie's Trainwreck Rooftop Deck - #Getdrunkhere - Bars Near Me - Chicago, Illinois

Arrived an hour and a half early for a bus to a concert. Already full. Okay! Bar super crowded, bartenders super busy. Okay! Ordered nachos, still hadn't come after an hour. Okay! No apology from the server. Not okay. Charged me for it anyways. Not okay. Ordered tequila shots. Not chilled, no lime. Not okay. The manger was cutting limes instead of helping frustrated customers. I certainly won't be back. read more

Trainwreck is an accurate description of the evening my group had. We were visiting from out of town and recommended Reggie as an nearby spot to grab dinner. Due to the size of the group were seated at 3 tables. Unfortunately the table I was seated at became the forgotten step child. We placed basic drink orders (beers & fountain sodas). The beers took 20 minutes to come, and the fountain sodas another 15. We placed appetizer orders and basically never heard or saw our waitress again. Our other two tables received their appetizers, and we thought ours should be coming soon. We were famished from a busy travel day, but rationalized: they are busy. So we waited. And waited. After an hour and a half our friends got their entrees. We had tried to find our waitress, but she kept avoiding us. Finally she came and told us they were out of Mac n Cheese, yet we ordered apps before our friends' tables and they clearly ate Mac n Cheese (they even shared some with us). This was already an hour after we ordered our apps. As our other tables were finishing their meals, a sympathetic waitress (from another table) finally helped track down our apps. What made matters worst was the bar manager argued with us on how long we waited. He was not apologetic, and questioned over and over how long we have been waiting. Even leaving to check in the system how long we have waited to prove a point. He also tried to justify why our other tables were served twice before we ever saw appetizers. Ultimately he did bring some complementary drinks and covered some of our meals, but the evening was ruined with the poor attitude of the serving staff and management. read more

Just not impressed with the service or quantity of food anymore. Restroom was nasty, they didn't have any wet wipes for the hands. The services was ok. read more

Mondays host is annoying and as a consumer I can't enjoy Reggie's because he talks too much. He's loud, obnoxious and says slightly racial and sexist comments. He should be fired, he needs to find a day job read more

Tldr: unprofessional staff harasses customers The atmosphere at this place is incredible: The pool table, the fire outside, the big tvs for watching the games, and the sound of whatever band is playing downstairs. Had a great night with my friends the whole evening, until my friend handed me her bill to bring up to the bar. I brought it to the bartender and walk off, only to hear "oh gee, thanks!" in the most sarcastic voice I've ever heard. I didn't think anything of it at first, until his buddy (presumably another employee) spouted "$7 on a $70 bill? Nice!" to me. Of course i apologized on behalf of my friend and gave the obviously upset bartender the last $5 i had on me to make up for the bad tip, and then accordingly i gave my friend shit for tipping so poorly. Do i think it was right that my friend stiffed the bartender? Absolutely not. Do i think if she had tipped like $3 more he wouldn't have said anything? Who knows. Is it right for someone to behave so unprofessionally after not getting a tip you should have gotten? Over like $5?? Absolutely not. Especially that his and his friend's behavior continued after i gave him the $5 more. His friend went outside and started violently stoking the flames in the pit so that embers got on my other friends - most of which were not involved in any way. In what world is it okay to go outside and harass customers? Grow up. read more

It was a cool June day when I was carried up to the Reggie's rooftop. Don't get me wrong, I like walking, but those stairs are pretty scary. I crossed the threshold and immediately liked what I saw. Hoomans with food abounded, as did comfy sitting spots. I started at a picnic table with some people I've never met before, but quickly became friends (they gave me their carrots). Then, just when I thought it couldn't get any better, daddy carried me to the couches. OH MY are those great! So much space, shady, and everyone came by to give me pats. I got chippos there too - even better than carrots! *Overall*: 5/5. Fantastic people, great seating, and all in the shade! Only thing missing was chicken, but this scnozz guarantees they have it! Location 4/5: It took a car ride to get there/back. I love riding in cars, but don't think I could walk this far. That probably means we won't be back a ton. Chairs 5/5: Couches, couches couches. The couches were amazing. I got 2 whole sections to myself, and didn't even need my normal cushion! Free stuff 5/5: All the waitresses offered me water, and everyone gave me food. Not sure if they have treats - but they had nachos, so who cares?! Ambiance 4/5: Rooftop spot means no traditional people watching, but I made plenty of friends since they were so busy. Trust me, there was plenty to do! Humans 5/5: So friendly and I got all the pats - randos, friends, waitresses, the whole 9! Wish someone had given me some chicken tho... read more

Oh Reggie you have done me wrong and all your Chicago patrons. How we've had many of good times on the train wreak roof top bar eating jumbo fried chicken wings and glorious pour-over craft beer. But last week I had to end my six year relationship with Reggie's Rock House. Showing up fashionably late as always, I happened to miss last call even though I stood at the bar for almost ten minutes with cash in hand. (Rude but I could care less) I did encounter the bar tender making a drink even though last call was over. This specific individual dug his dirty hands into the big steel container of ice to make his Manager's friend a drink. Yes you heard right dug his hand into the container of ice that serves you mixed drinks and water. This is filthy disturbing and a total violation of Heath codes. I must say the management of their people and lack of respect for their patrons has lost any Appetite of ever returning to Reggie's read more

Love love love this place! It was so beautiful outsi and my first time being here! We went on a Wednesday around 4:30 and the rooftop wasn't packed yet - also there were $5 long islands, $5 margaritas and some other specialties; also 1/2 price Apps -TVs all around, couches and a nice music selection... WIN! I'll definitely be back! read more

Reggie's Trainwreck Rooftop Deck - Beautiful scenery/view - Bars Near Me - Chicago, Illinois

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