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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?
    Live music
    Divey
    Casual
    Moderate noise

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    Recommended Reviews - Reggie's Trainwreck Rooftop Deck

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    Reviews With Photos

    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.

    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.

    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. *

    All Day IPA

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    9 years ago

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    14 years ago

    Rooftop basketball, free pool, bags, outdoor shower, food and booze. Amazing.

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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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    Photo of Dave B.
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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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    12 years ago

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    10 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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    8 years ago

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    10 years ago

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    11 years ago

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    9 years ago

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    12 years ago

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    12 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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    12 years ago

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    10 years ago

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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

    Read more highlights

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    We hit up the Arc Bar for a bite and a drink after visiting the Auto Show. We sat at the bar and…read morehad really terrific service from the bartender, Vince. He was friendly, fast and efficient and really seemed to care that we had a good experience. I believe in calling out exceptional service professionals and Vince is definitely that. Drinks were tasty, food came out quickly and we had fun watching the Olympics at the nicely appointed bar this Sunday afternoon! Cheers, Arc Bar!

    I was here for a conference and needed something easy for dinner. I ended up sitting by the bar…read moreafter debating on taking the food to go and eating upstairs in my room. The service was super quick and my server/bartender was great! It seemed like she barely put my order in the computer and then the food magically appeared. She anticipated my needs and was very accommodating. The food was decent and the wings were generous. I ended up eating all of it! The lime ancho chile rub was surprisingly delicious and you can't go wrong with buffalo wing flavor. She gave me two blue cheese sauces so I was able to douse the wings with more than enough sauce. I ended up taking my dessert back upstairs. I wasn't sure why they called it Grown Up banana pudding but it was a creative spin to banana pudding. It was different but also not bad. I'm still not sure what I think of it. Overall, this was such a convenient spot for dinner (and lunch) while in the area for a convention.

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

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