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    Reggie's Trainwreck Rooftop Deck

    3.4 (104 reviews)
    ModerateBars
    Open 11:00 am - 2:00 AM (Next day)

    Reggie's Trainwreck Rooftop Deck Photos

    REGGIE'S TRAINWRECK ROOFTOP DECK ATMOSPHERE

    What's the vibe?
    Divey
    Casual
    Moderate noise
    Live music

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    Recommended Reviews - Reggie's Trainwreck Rooftop Deck

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    Outside
    Steve A.

    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.

    Huge fried pickle spears
    Christina B.

    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.

    the outdoor dining area
    Dakota B.

    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.

    Janelle S.

    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. *

    bar area

    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.

    All Day IPA

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    10 years ago

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    11 years ago

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    12 years ago

    Fun place to have a few drinks with friends, shoot a few hoops, & enjoy some delicious chilli-mac!!

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    14 years ago

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    12 years ago

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    13 years ago

    Great spot great food. Best fried pickles I ever had, the wings were pretty good too.

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    12 years ago

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    11 years ago

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    11 years ago

    Best wings in the Chi. Got me through last winter. Keep doing specials!

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    9 years ago

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    10 years ago

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    11 years ago

    This place was awesome, beers were cheap workers have a great attitude, ambiance was nice. I will definitely go back.

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    12 years ago

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    11 years ago

    Love going there on Tuesday nights with my friends for the wings upstairs is way better then down stairs

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    Page 3 of 3

    Ask the Community - Reggie's Trainwreck Rooftop Deck

    Review Highlights - Reggie's Trainwreck Rooftop Deck

    Really, REALLY good barbeque ribs AND a free pool table.

    Mentioned in 3 reviews

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    Apolonia - Pistachio ice cream

    Apolonia

    4.4(342 reviews)
    0.2 miNear Southside
    $$$

    Had a casual dinner here over a weekend Drinks were on…read morepoint and boozy The bread was phenomenal The pastas are fresh in house and all of the food was great Overall would recommend to anyone - veggie friendly as well

    Apolonia offered excellent food, but I will never go back…read more We ordered the tasting menu ($72) and added the wine pairing ($48) and with tax and tip the bill for two was just under $320. None of this was a great surprise. No cocktails, by the way. The tasting menu was photocopies with two menus per sheet of paper and a very sloppy cut for a non-rectangular menu. The problem was the service. I like a paced meal but 2 hr-55 min is absolutely ridiculous. The restaurant was not able to get food onto the table, either because of the quantity of quality of the staff, and the room certainly wasn't very crowded, perhaps 35 customers in sight. I think there were 4 cooks, 2 servers, 2-3 runners/busboys, and a hostess who hustled around doing a lot of odd jobs. Every item served was delicious. The plating was nice as well. The wines were not so successful. Of the four wines on the menu, two differed from the descriptions and the pairings ran from OK to Combative. I have lots of details about the food and wine, but that's not the issue. The poor service was inexcusable. I only get to Chicago one every 2-3 years and there are so many good restaurants that this one has been crossed of the list with a permanent Sharpie.

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    Apolonia - 08.21.25 Kale and brussels sprouts was also good.

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    08.21.25 Kale and brussels sprouts was also good.

    Reggie's Trainwreck Rooftop Deck - bars - Updated September 2026

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