Tipsy Cow Cantina

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16 Reviews
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$30 and under
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Live Music Nightly Free Chips and Salsa Always Drink Specials Daily Mexican Street Food- Tortas, Tacos, Salads
Dining Style
Casual Dining
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Mexican, Tex-Mex, Southwest
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Hours of operation
Tue–Sun 5:00 pm–10:00 pm
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Phone number
(773) 283-5545
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Payment options
AMEX, Discover, MasterCard, Visa
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Dress code
Casual Dress
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Executive chef
Gregg Readdy
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Cross street
Lawrence Ave. and Central Ave.
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Public transit
1.5 blocks from Jefferson Park Transportation Center (CTA, Pace, Metra)
85 Central Bus
81W Lawrence Bus
Beer, Cocktails, Full Bar, Gluten-free Menu, Happy Hour, Takeout, Wine
What 16 People Are SayingWrite a review
Overall ratings and reviews
3.9based on all time ratings
Noise · Moderate
87% of people would recommend it to a friend
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1 review
Dined on May 12, 2018
Overall 3food 2service 5ambience 5

Great and friendly staff. I noted on my reservation that it was a special occasion (ie. a bunch of tired mommas having a get together without their kids in tow for once) and there was a cute balloon tied to a chair at our table.

Food... just ok. The guacamole and salsa were really good but my salad bowl was ehh. The lettuce was too soggy, it was more like half soup/half salad. Then we wanted to get dessert but they no longer carried the dessert that was on the menu.

Live entertainment...I always love live music but it was way too loud. We couldn’t hear each other talk over the table.

3 reviews
Dined on May 12, 2018
Overall 5food 5service 5ambience 5

We love this little gem in our neighborhood! Great food, drinks and music!

3 reviews
Dined on May 5, 2018
Overall 2food 2service 1ambience 4

Loved the music but our service was subpart. I went to celebrate 5 de Mayo, and they were playing 60s music. The food wasn't authentic. Drinks were light... I don't think I'm coming back.

15 reviews
Dined on April 17, 2018
Overall 5food 5service 5ambience 5

love the taco tuesdays with live music- food is great, fresh, great margaritas

1 review
Dined on March 22, 2018
Overall 5food 5service 5ambience 5

Live music was great! Fun little restaurant and bar.

21 reviews
Dined on March 9, 2018
Overall 2food 2service 4ambience 4

This was our first time going to the Tipsy Cow. We went on a Friday evening at 5:45… the crowds didn’t roll in until we were leaving.
We decided to order the 3 taco dinners. Because there are 5 different fillings, we decided to order all 5 between the both of us so that we could check them all out. The only one that we both really loved the flavor was the beef. There was nothing spectacular about the rest. The sides - beans and rice - were disappointing… the beans were too spicy and the rice too bland.
The service was good. I was pleased with the buckets of chips on each table and squeeze bottles with 2 different salsas. We enjoyed the live music. Overall, the food was nothing outstanding.

10 reviews
Dined on February 17, 2018
Overall 4food 4service 4ambience 4

Been here twice now and we really like it. Food, service & drinks are good and reasonably priced. Friend had hibiscus margarita, said best she's had. Having the live music makes the place that much better & supporting local artists, didn't think it was too loud. Love the games. We will definitely be back.

15 reviews
Dined on February 6, 2018
Overall 5food 5service 5ambience 5

Love this place! Taco Tuesdays fun- $1 tacos and great live music! Neighborhood gem! Will definitely visit again and often.

2 reviews
Dined on January 23, 2018
Overall 3food 3service 4ambience 3

The food was alright, definitely not authentic Mexican food

8 reviews
Dined on January 20, 2018
Overall 4food 3service 3ambience 3

Overall good to see the location get another shot at a restaurant. The food was ok but I was underwhelmed. The beer selection is GREAT. Tacos were ok but steak was over cooked. Best thing was the beans. Delish!

88 reviews
Dined on January 19, 2018
Overall 1food 1service 1ambience 1

Where to start- it was bad, bad and bad.
"Cantina" trying to be a large bar, live music venue and restaurant all in one- doesn't work!
Live music is great, when you have the right space. The person singing and playing was so darn loud, we were miserable- zero conversation.
For a cantina, it had entirely too many TVs to boot- here trying to also be a bar, not enough space and too many mixed vibes going on, so confusing.
Service was fair at best, literally had to find our waitress for more water and the bill.
We ordered the Jalapeno cheese sticks, empanadas and chicken quesadilla- all of which we didn't finish any of, the breading on the sticks and empanadas was enough to choke you. The quesadilla was nothing special.
The noise and bad service just made us want to run out of there.
We really wanted to support the local spot, but not this one, unfortunately.

1 review
Dined on January 10, 2018
Overall 5food 5service 5ambience 5

The waitstaff and cook/manager went above and beyond to make for a very enjoyable evening in ambiance and food service. The entertainment was fabulous! Five Star !!!

1 review
Dined on December 31, 2017
Overall 4food 4service 4ambience 4

We enjoyed our meal at the Tipsy Cow Cantina. It was reasonably priced. There was parking. The food was enjoyable and we had our share of chips and homemade salsa. I'm sure that we'll be back.

40 reviews
Dined on December 29, 2017
Overall 4food 4service 5ambience 4

Having no idea what to expect on turning up to the Tipsy Cow Cantina on a cold and blustery winter night, we were pleasantly surprised to discover a comfortable, cozy local gem of an establishment.

The place is nicely eccentric: decorations are reminiscent of a Mexican cantina (appropriately), and you relocate a tipsy cow (!) to indicate need for service. Live music through the evening keeps the noise levels up.

Margaritas are inventive and tasty, though the beer list might be considered eclectic, with oddities that are worth trying, but the range is decent and there is something for everyone. The food was that rare combination of cheap and delicious; accompanied with attentive service, this was a memorable evening and we will return.

Reservations recommended!

4 reviews
Dined on December 29, 2017
Overall 5food 5service 5ambience 5

Fun place. Good food. Great service. Fun music. Small food menu but great drink menu. Will be back.

2 reviews
Dined on December 28, 2017
Overall 5food 5service 4ambience 5