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    Reggie's Trainwreck Rooftop Deck

    3.4 (103 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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    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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    1 year ago

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

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    3 years ago

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

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    5 years ago

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

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    Page 1 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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    Woven + Bound Restaurant

    Woven + Bound Restaurant

    (56 reviews)

    $$$

    Near Southside

    This is inside the Marriott Marquis in downtown Chicago. As soon as we checked into the hotel, we…read moredecided to go downstairs and get some food to eat. I ended up getting a grilled cheese sandwich and my date got the burnt pork belly ends. I believe it was called. We ate there about midday on a Monday. It wasn't too busy as most people hadn't gotten in for the huge convention yet for Ace Hardware. The tomato soup was very delicious. I wanted croutons and they had some sort of croutons, but they were a little different than when I was used to. They only have Pepsi products and I'm more of a Coke girl. On her last night there we returned there as well for dinner. I will post pictures of the food. My date had the burger which he said was super delicious and it was very big and I had the chicken Caesar salad, which was pretty good. The bar was very bustling with a lot of business folks. It was so convenient just to walk downstairs and go have a meal and not worry about going anywhere on our last night since we had early flights the next morning. The only thing I had an issue with was the fact that our waitress had left for the evening and did not notify us and we sat there for a bit before we got a check and I was told that she had given her duties to another server which we had no idea . Poor communication on her part. We did have margaritas the first time we got there and they were pretty delicious. The truffle fries were good as well. Our first server was pretty attentive, but that might've been because it was not quite busy. The first time we went. If I was to stay in that hotel again, I would stop by for some food.

    We were able to get seated here as a party of 4 without a reservation on a weekend which was nice…read more The restaurant is in the hotel and there's lots of tables. View is also decent with big windows and good natural lighting. To start we got the fries and Brussel sprouts. Both were super good. The brussel sprouts came with jalapeños in it which went well together. I love that there are so many vegetarian options here. I got the mushroom steak which was a cool unique dish. The gravy it comes in was yummy. For sides I got the Mac and cheese and garlic mashed potatoes which were both delicious. I got the mule cocktail twice and it was so good I would definitely get it again. Could barely taste the alcohol. For dessert we got the strawberry tres leches which is again a unique dish and a very vibrant color. The only thing I'd say is that the service here wasn't too good. They also brought out our bill prematurely when we weren't done ordering more food and drinks.

    Apolonia - Pistachio ice cream

    Apolonia

    (325 reviews)

    $$$

    Near Southside

    I like this restaurant--not my first time as I am often at the McCormick Convention Center for…read moremeetings and am looking for something within walking distance but also a little bit removed. The staff are friendly and attentive; the space is appealing--bright and simple. At the time of my visit, which was at opening for lunch at 11:30, it was quiet, but was more lively by the time I wrapped up. I had the blue crab bucatini and loved it. My only complaint that I could have eaten twice as much as the portion (which was reasonable, though).

    I was trying to decide on a final location to dine at for restaurant week and happened upon…read moreApolonia. Made a reservation and was seated right away on a Sunday for brunch. I loved the modern interior and child enjoyed the fuzzy, soft undersides of the tables. I ordered from the restaurant week menu and had the following: warm seafood salad (calamar, octopus, lemon vinaigrette), cacio e pepe' polenta (brisket ragù, sunny egg), and cinnamon roll. I didn't care for the warm seafood salad as it was overly oily and passed it off to hubby to finish. The cacio e pepe polenta was good but the portion size was so small I finished it in like 3 bites. I was excited for the cinnamon roll but it was a letdown. Our friend who dined with us described it as the "driest cinnamon roll he has ever eaten." I ordered the frittata Española (potatoes, fontina, piperade) for my child which was pretty standard. There was maybe a 30 minute delay between the time we finished each dish and when the next one would appear. The restaurant wasn't terribly busy but there seemed like there were only 2 chefs working at the time.

    VU Rooftop - Brunch buffet + bottomless mimosas at VU!

    VU Rooftop

    (387 reviews)

    $$

    Near Southside

    Visited a few times for happy hour during my stay the…read moreambience is fantastic especially on the deck the fire pits are warm and cozy, food average bar food with the exception of the shrimp- big juicy and delicious from the hostess to the servers everyone was plant and accommodating if your are looking for a good happy hour experience on a beautiful day - make it a stop

    Here's a revised version with the view included:…read more I've visited VU Rooftop several times and it's always a great experience overall. The ambience is one of my favorite things about this place -- the atmosphere, the music, and the beautiful view from the 22nd floor always make it feel like a special night out in the city. The service during my most recent visit was great. Sarah, our server, was amazing -- attentive, friendly, and made sure we had everything we needed throughout the evening. Unfortunately, this was the first time I didn't enjoy my food. I ordered the grilled chicken skewer appetizer, and while it looked good, something about the flavor just didn't sit well with my taste buds. It may simply come down to personal preference, but it wasn't something I particularly enjoyed. One thing I do appreciate about VU Rooftop is that their menu changes seasonally, which always allows for a new experience each time I patronize. Even though the food didn't quite hit the mark for me this time, it won't stop me from returning. The ambience, service, and those 22nd-floor views of the city are always worth the visit. I'll definitely be back -- I'll just probably skip the grilled chicken skewer appetizer next time.

    Brando's Speakeasy - Karaoke bar

    Brando's Speakeasy

    (656 reviews)

    $$

    The Loop

    Such a fun vibe and a great crowd! I went in on a Sunday evening and it was decently packed. The…read morebar itself is dimly lit and moody. There's plenty of booth seating, as well as tall chairs at the bar. Once it was karaoke hour, I put myself on the list and started singing. Everybody is fun about it, whether the performer is conventionally a great singer or not, and I absolutely love it! There was even a group of 4+ girls who sang together on stage, and the energy was so infectious, it got the whole bar yelling the lyrics along with them. Would highly recommend!

    Stopped in with friends and ended up having a much better night than we expected. The place has…read morethis fun mix of old-school charm and lively energy, and it really comes alive once the crowd settles in. What surprised me most was how welcoming the atmosphere felt -- people were cheering each other on during karaoke, and it created this upbeat, easygoing vibe that made the night even better. Drinks were well-made, the music kept the room energized, and there was always something going on that pulled everyone into the moment. Even with the place getting busier later in the night, the staff stayed attentive and kept everything running smoothly without making anyone feel rushed. I also loved how organized the karaoke setup was. Being able to add songs without waiting around made the experience feel seamless, and it helped keep the energy flowing. It's the kind of spot where you can unwind, have a laugh, grab something tasty, and forget about your week for a while. All in all, it turned out to be one of those unexpectedly great nights out. I'd absolutely come back and recommend it to anyone looking for a fun, relaxed place to hang out and enjoy some good music and good company.

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

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