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Rudy and Ann's

4.3 (6 reviews)
InexpensiveBars

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5 years ago

Great neighborhood tavern! Everyone was welcoming, employees and patrons. Stop in if you're in the neighborhood.

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3 years ago

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17 years ago

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6 years ago

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14 years ago

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10 years ago

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Osito's Tap

Osito's Tap

4.3
(73 reviews)
3.9 mi
•$$

My first time here and it might be one of my new favorite bars in Chicago! First, I love the…read morespeakeasy vibe. It's located inside of a brightly lit liquor store, and it's a completely different vibe as soon as you enter into Osito's Tap. At 8:30pm on a Saturday, we were seated right away at the bar. There was a live DJ, but the music wasn't too loud which I appreciated. Sometimes with live DJs the music gets way too loud, but it was just some nice background music. The service was great, and our bartender was really friendly. We tried the For Ari, Nube Punch, and Jardinera. All the cocktails were delicious and unique. I typically don't like savory cocktails and usually cocktails with malort are intimidating, but the jardinera cocktail surprised me and I actually liked it a lot. I think the tomato flavor just worked really well with the malort. I would come back just for that cocktail, but there were so many other cocktails I wanted to try and didn't get to this time, so we'll definitely be back.

I was really excited to try Osito's!…read more The space itself is lovely and moody. We tried a handful of things from the menu but would have tried more, but as they got busier, the service declined. Everything we tried was delicious--especially the salsas! Their drink menu was fun and interesting so I would definitely recommend stopping by for a few drinks.

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Quezatlin - my Favorite
Quezatlin - my Favorite
Osito's Tap
Duck Tacos, Wings, and Chicken Thigh

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Duck Tacos, Wings, and Chicken Thigh
La Cueva

La Cueva

3.4
(9 reviews)
3.6 mi
•$$

What a wonderful place with many friendly people...we sat through a most festive drag show with…read morelots dancing...I really had a difficult time guessing genders or preferences but I had so much fun I kept ordering drinks...can't wait to go back...nothing like this in New York, Los Angeles. ..Long Beach or any other place I've visitied...and I have visited a lot...even better than Mexico City...

This is a scary place to see female impersonators. You have to pay attention in order to find it,…read morethe only thing that barracdes it from the font of 26th street is a wrought iron fence, but don't blink, its not a nice looking outside. Inside is okay though. First off, if you are not intimidated by the rough neighborhood, let their bathrooms scare you out of there, somewhat. I mean when you are walking and the floor tile comes up with you, this is not a good sign. Years ago, this place (which by the way has been around since the early 80's or maybe even the 70's), was not a bad hidden place. But as the years went on, the owner (Juanita Banana), turned it into a really thriving business. On any given day you could see the cowboys of Mexico show up there (why are married men in a gay bar), and just drink away the night while getting a glimpse of female impersonations. And really not a bad group, but you will probably need to speak the native language in order to understand. Very few touch on english music but sometimes if your lucky, you will see a Gaga impersonator. the drinks can be less expensive for the venue, but hey it is what it is. A mixture of gay and "straight" men in the joint, but you be the judge.

Photos
Miss Ketty
Miss Ketty
The hidden "Cueva" or Cave. Chicago's notable queens had
The hidden "Cueva" or Cave. Chicago's notable queens had
La Cueva

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Jacaranda

Jacaranda

4.7
(10 reviews)
4.0 mi
•$

My business partner and I went to La Villita to watch México tear up RSA in the first match of this…read moreyear's World Cup. We stumbled across Jacaranda bar which we soon found out is a hidden gem. We were welcomed by dozens of fellow México fans who -- like us -- were dressed up in the tricolor. The energy was electric. Despite how busy they were, the staff went out of their way to offer us great seats at one of the tables with a perfect view of their televisions which were of course featuring the game. They even had free raffle giveaways as well as complementary fresh homemade ceviche for all of the guests. This truly was hospitality at its finest, and it was paired so nicely with the friendly and generous patrons of this establishment. We certainly intend to return as soon as possible to watch more fútbol and appreciate the fantastic la Villita community.

Great service and fun atmosphere. The drinks were decently strong, but they mostly had well and mid…read moreshelf liqour. The prices were very in line with what they served, and they tasted great. My family has a fun connection to this location as the apartment above the bar was my family's first home when they immigrated to America from West Bohemia in 1903. There's much more to that story, but it's what's appropriate for this review.

Photos
Jack & Coke
Jack & Coke
Weekend Bar Tender Andrea preparing a cocktail for a customer on Jacaranda's 50th Anniversary Celebration Party in May 2015!!
Weekend Bar Tender Andrea preparing a cocktail for a customer on Jacaranda's 50th Anniversary Celebration Party in May 2015!!
Jacaranda

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Low Horse

Low Horse

4.9
(8 reviews)
9.1 mi

First off, I loved the vibe of the bartender! They were super friendly and welcoming. Truly the…read moreembodiment of Low Horse (opposite of high horse). Second, I love the vast array of games they have! I came because I saw they had a super Nintendo, but then I saw this huge game set-up at one of the tables which I learned is a 19th century Canadian game called Crokinole. With a quick Google search we learned the rules in a few minutes and had a blast. I love the tactile feel of these types of games and the classic formula of "shoot item in hole". Service was great, the beers came out quickly and the bartender even brought my credit card out since I forgot it. I asked about the Super Nintendo and they checked to make sure it was on and basically it's first come first serve! They also have the original NES in the back somewhere and a whole selection of board games to play. On the super Nintendo that have a curated selection of classics like Donkey Kong Country, Mario Kart, Super Mario world, and Super Street Fighter 2. It was such a throwback to be able to play these games and felt great to share a bit of my childhood with my wife. There's nothing like spamming punch with E Honda and destroying your partner over a few beers. Low Horse is a great bar in Wicker Park with a vast selection of games and perfect for catching up with friends!

Great service, nice ambience, average priced and well made drinks. Bar stools are wiggly as hell…read moreand not comfy. Lots of games to play!Overall definitely worth a few visits.

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Original Mario kart on Super Nintendo!
Original Mario kart on Super Nintendo!
Great vibes and a visit from the tamale guy!!!
Great vibes and a visit from the tamale guy!!!
Low Horse

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Rudy and Ann's - bars - Updated July 2026

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