Cancel

Open app

Search

Reggie's Trainwreck Rooftop Deck

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

REGGIE'S TRAINWRECK ROOFTOP DECK · YELP ASSISTANT

Ask Yelp Assistant

Reggie's Trainwreck Rooftop Deck Photos

REGGIE'S TRAINWRECK ROOFTOP DECK ATMOSPHERE

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

You might also consider

More like Reggie's Trainwreck Rooftop Deck

Recommended Reviews - Reggie's Trainwreck Rooftop Deck

Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
Yelp app icon
Browse more easily on the app
Review Feed Illustration

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.

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

See all

Photo of Andre W.
572
2130
1459

10 years ago

Helpful 4
Thanks 0
Love this 0
Oh no 0

11 years ago

Helpful 1
Thanks 0
Love this 1
Oh no 0

10 years ago

Helpful 2
Thanks 0
Love this 1
Oh no 0

13 years ago

Helpful 2
Thanks 0
Love this 4
Oh no 0

13 years ago

Helpful 3
Thanks 0
Love this 1
Oh no 0

13 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0
Photo of Kay M.
70
38
76

7 years ago

Helpful 0
Thanks 0
Love this 1
Oh no 0

8 years ago

Helpful 3
Thanks 0
Love this 1
Oh no 0

7 years ago

Awesome service. Professional through and through. Bouncers with IQs above 65. Not to be missed.

Helpful 0
Thanks 0
Love this 0
Oh no 0

10 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0
Photo of Ravi M.
10
39
4

9 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

6 years ago

Helpful 3
Thanks 0
Love this 0
Oh no 0

12 years ago

Helpful 0
Thanks 0
Love this 1
Oh no 0

7 years ago

I love this one,great place,music,food and cheap drinks!!!I highly recommend this place!

Helpful 0
Thanks 0
Love this 0
Oh no 0
Photo of Dan R.
28
13
6

8 years ago

Cool place. Live music great vibe. Cool people. Will go back daily if I go to RSNA again.

Helpful 0
Thanks 0
Love this 0
Oh no 0

10 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

6 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0
Photo of Em A.
2
215
0

8 years ago

Nice place to hang out during the summer. Beers are cheap. Food is good. They even have a shower to cool off under I'm the summer.

Helpful 0
Thanks 0
Love this 0
Oh no 0

5 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0

11 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0
Photo of Lee M.
55
23
1

8 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0
Photo of Jan M.
230
6
1

8 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

12 years ago

Helpful 2
Thanks 0
Love this 2
Oh no 0

10 years ago

Helpful 4
Thanks 0
Love this 2
Oh no 0
Photo of Steven S.
15
12
23

10 years ago

Helpful 2
Thanks 0
Love this 4
Oh no 0

7 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0
Photo of Erika H.
146
24
58

10 years ago

Helpful 1
Thanks 0
Love this 1
Oh no 0

9 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0
Photo of Vegaz- T.
1029
18
6

7 years ago

Helpful 0
Thanks 0
Love this 1
Oh no 0

7 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

8 years ago

sick place to have some fun. been my spot for years, keeps gettin better. Great to grab some eats and drinks before or after a show.

Helpful 0
Thanks 0
Love this 0
Oh no 0

10 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0
Photo of Nat H.
208
36
6

12 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0
Photo of X B.
2
23
0

12 years ago

Helpful 1
Thanks 0
Love this 1
Oh no 0

12 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0

8 years ago

Helpful 2
Thanks 0
Love this 0
Oh no 0

11 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0
Photo of L L.
36
955
4737

10 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

7 years ago

Good time. Easy spot to get to... Train or street parking. The service was good. The chicken wings were delicious.

Helpful 0
Thanks 0
Love this 0
Oh no 0

14 years ago

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

Helpful 1
Thanks 0
Love this 0
Oh no 0

Page 2 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

You might also consider

Verify this business for free

People searched for Bars 22,258 times last month within 10 miles of this business.

Verify this business

Fatpour Tap Works McCormick - Coastal Cobb Salad

Fatpour Tap Works McCormick

3.9(442 reviews)
0.2 mi•Near Southside
•$$

My husband and I were seated upstairs for NFL Sunday. Jess was warm, funny, knowledgeable and…read moregenuinely invested in making sure we had a great experience. She asked what we liked, helped us navigate the beer selection and recommended a hazy that was spot on. While we were still talking, our beers magically appeared. She laughed and said, "Welcome to Fatpour. This is the service you'll always receive here." That perfectly captured Jess. She wasn't just doing her job--she genuinely cared. We noticed the same woman constantly jumping in to help the staff. Jess smiled and called her the "captain of this ship." Watching her manager work was just as impressive. She wasn't standing around acting like the boss she was right beside her team bringing drinks, grabbing dishes and helping wherever needed. We asked Jess if she ever felt nervous having her manager around, who we found out is the General Manager and her answer said everything. she loves when her manager is there. She told us her manager supports her, teaches rather than tears people down, and still holds everyone accountable when necessary. Jess told us she has felt supported all around since her first day and that her colleagues have truly become like a family. Honorable shoutout also to the gentleman who was working amongst them with the rad leg tattoo! We dont hope just Fat Pour is here next time we visit but that this same crew is here

Good place to go if you arrive late to the hotel and need a bite to eat. They closed at 2am…read more Your basic bar scene, mult-TV screens with games on. Typical bar food, appetizers, pizza, handhelds, drinks...etc. Nice staff. Food was average. It's not bad but it's not amazing either but it will be satisfied for foods

Photos
Fatpour Tap Works McCormick - Crabcakes, mushrooms, and brussels sprouts side

Crabcakes, mushrooms, and brussels sprouts side

Fatpour Tap Works McCormick - Roasted Half Chicken

Roasted Half Chicken

Fatpour Tap Works McCormick - Fatpour Smash Burger

See all

Fatpour Smash Burger

Best Bar

Best Bar

4.3(68 reviews)
0.3 mi•Chinatown

With trendy decor and a unique variety of drinks, Best Bar is 100% a hidden gem. I'm not sure why…read morethis place isn't more popular, but this is your sign to stop by! We stopped by around 9:30pm on a Saturday after unsuccessfully trying to find a spot at some neighboring bars. The bartender was super friendly and attentive, making everyone feel right at home. The vibe itself sits somewhere between a dive and cocktail bar, so it's a great spot to relax if you want to feel just a little fancy without actually having to dress up. I can't remember the exact names, but the drinks we opted for were essentially unique takes on a lychee martini and espresso pistachio martini. The lychee martini was not too sweet at all and had a lovely, refreshing hint of pear with a tasty, crunchy sugar rim. The espresso martini was super creamy without being rich, and was also very pistachio forward. I love when what seems to be an amalgamation of flavors comes together into a perfectly balanced whole, and these drinks hit the mark. I will absolutely be back to try more of the menu, and can't recommend this spot enough if you find yourself in the area!

Always a good pure and inviting vibe in this place…read more The bartenders are really nice and quick with service. Theres a lounge area and a displays of tvs to watch as well. They serve thc drinks for those who garden and dont drink alcohol! I love the bars that have them.

Photos
Best Bar
Best Bar
Best Bar

See all

Apolonia - Pistachio ice cream

Apolonia

4.4(346 reviews)
0.2 mi•Near Southside
•$$$

Apolonia absolutely deserves 5 stars for the brunch service. My daughter and I were looking for…read morebreakfast around 11:00 this past Sunday, only to find many places ended breakfast before that. Apologies was nearby our hotel, the Marriott Marquis. We started with a cappuccino and an O.J. Both were perfect and my daughter commented that it tasted like they had just fresh squeezed the oranges moments ago. We considered ordering the pastry tower, but instead opted to share three dishes. It eneded up being more food than we could finish. Portion sizes were big, especially for the quality and price. We shared 1 savory and 2 sweet dishes: the banana business croissant, the warm cinnamon roll, and the fritatta Espinosa. Each one completely impressed us and we're so delicious. We told the server we couldn't belive they were both baking high end pastries like this and preparing amazing savory dishes. Overall, our service was quick and friendly. The room was clean, spacious and modern. If I visit Chicago again from the East Coast, I would happily visit Apolonia again. I would love to try some of the brunch drinks and more items.

We were looking for somewhere to get dinner before a concert at Soldier Field and I'd had this…read moreplace bookmarked (mostly for their pastries which we didn't try but I liked this meal enough to go back and try those things). They were really fast and good at getting us out super promptly, which was appreciated. I didn't take a photo of everything we ate so I don't remember all of what we ordered. The food was good but a four stars because some items were really delicious (the black truffle bread and mussels toast for example, maybe some of the pastas) but some of the items were just fine (e.g., red prawn carpaccio). If Yelp did fractional stars, I'd probably do a 4.5 or 4.25, but because the food is more expensive I expect every dish to be more impressive. I found the pistachio dessert that a lot of people mentioned in the reviews to be underwhelming although fun to look at (however what I care about is taste).

Photos
Apolonia - Bar

Bar

Apolonia - Salmon crudo

Salmon crudo

Apolonia - 08.21.25 Kale and brussels sprouts was also good.

See all

08.21.25 Kale and brussels sprouts was also good.

The Staley - Meat lovers pizza

The Staley

3.5(57 reviews)
0.3 mi•Near Southside

Always a good time when greeted by AGM Joey at The Staley, cheering on the fighting Illini and the…read moresuper huge and plentiful TV screens, and enjoying the delicious breakfast pizza prepared by sous chef Christopher. It's my new favorite pizza, made with fresh egg, gooey cheese and chunks of bacon (not itty-bitty bacon bits)! Shared with my friend the always, fresh hot, decadent chocolate cookie skillet with a huge scoop of vanilla ice cream and drizzled with generous amounts of chocolate syrup! The new general manager, Vincente, graciously introduced himself - how nice to have a charming caring GM making you feel special. Thank you :) The place is always clean, organized, and the wait staff is consistently friendly professional and efficient.

We visited for the first Bears game of the season and had the BEST time. Alondra was our server and…read moreher customer service is what led me to writing a review. We got there early to secure a good seat for the game, and from the moment we arrived she was high energy and extremely attentive. I never felt like I had to ask her for anything because she anticipated our group's needs extremely well, and any recommendation she had like ordering more shots, we happily to took her up on it. The screens are the perfect size for an event like this, the birria nachos are a standout; and I appreciate when the bar chills my glass for a martini, which they did. Overall a fun place to watch the game with other fans (this is a very social place), and we'll absolutely be back this season. Thanks Alondra!

Photos
The Staley - Game area

Game area

The Staley - Brussels sprouts

Brussels sprouts

The Staley - Boneless chicken nuggets

See all

Boneless chicken nuggets

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

Loading...
Loading...
Loading...