I lived in the area from 2008-2009 and found this place one night, loved it and frequented it often. Nice small cash-only neighborhood bar, bartenders always introduced themselves to you off the bat, many nights sitting around with a group of people of varying ages and jobs, all taking turns buying each other rounds- I stop by when I visit Chicago every few years and always a nice spot. People say if you are new the regulars stop and stare, not sure how valid that is but I spent age 30-31 there and now stop by in my early 40's so I don't care, and I have run into a few regulars who remembered me after a few minutes of chat. Clean and safe spot with great service and awesome owner/owners read more

Really cool neighborhood dive bar. Very clean. Fun decor and art work. I appreciated the Prince painting. I also appreciated the old school pinball machine and pool table. Helpful and friendly service. The bartender was great. They do mystery shots here and I appreciate the fun, and they're only $2! You roll a dice and see which number you get. None of the mystery bottles are straight liquor, which is a relief. They are all mixes. The mystery shot I had smelled really good and tasted sweet. I also had a cocktail. For a dive bar, the cocktail prices seemed a little high ($14) at first, but I can tell they use good quality ingredients for these craft cocktails so it makes sense. I had the Port in the Storm and it was okay. I couldn't really taste the flavors listed, especially the rum. My friend had a glass of rosé and the pour seemed a little small. I noticed they have a really nice happy hour with 50% off many items so I'll have to come back for that. Welcoming atmosphere and positive vibes. I would definitely come here again. read more

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My lovely wife wanted to check out a new dive bar, so we wandered into Teddy Bear Lounge, located on Pulaski a bit south of Addison. The establishment actually has two entrances, though the place would not seem large enough to have two of them. There is one teddy bear in the house (otherwise it might be called "Teddy Bears" ?). Our server was kind, and she mentioned right away that they were a cash only bar. We had some beers, watched some bad baseball on TV, and listened to an eclectic selection of music during our Saturday afternoon visit. The framed photos of Chicago sports venues remind you that this is a sports bar. read more

Despite Teddy Bear Lounge being close to home, we had never stopped in. We did so, and it was a very chill atmosphere with a personable bartender and enough of a beer selection that we easily selected libations to enjoy. This is definitely a no-frills place, but I happen to really appreciate that in a neighborhood bar. As with most small bars, the beer selection is not huge, but it's good. I hope to stop back in sometime in the near future. read more

Teddy Bear Lounge - Dive Bars Near Me - Chicago, Illinois

Husb and I came into Teddy Bear on an impromptu bar crawl to a friend's house for New Year's Eve. Teddy Bear is a textbook local dive bar so we were eyeballed upon entry because we've obviously never been in here before but, in usual dive bar fashion, were immediately welcomed in by everyone at the bar. It's cash only in here but a Blue Moon and High Life only cost us $9. Christmas decorations are nice. They have a pool table, jukebox, and it is sparkling clean! It's honestly the cleanest dive bar I've ever been in. The bartender that evening was Mikaela and she was so friendly - introduced herself and asked our names as well. read more

Teddy Bear Lounge - I spy the Teddy Bear at the bar. - Dive Bars Near Me - Chicago, Illinois

Our new favorite neighborhood spot! Cocktails were fantastic, service phenomenal, ambience is this great mix of fancy drinks inside a laid back neighborhood staple. Make it a bear night with happy hour at Teddy Bear and dinner at Big Bear right down the street. read more

Johnny & Cheryl, the new owners have completely embraced the neighborhood and the long-time regulars. This place is an absolute gem on Pulaski. Great place to watch the Bears, grab a cocktail or a local craft beer. Proprietors recent renovations are absolutely gorgeous. Make it yours before everyone finds it! read more

Came in on a Sat morning around 11am, by happenstance. One small window. 2 patrons, one who was asleep and one who had a hospital bracelet on. NCIS was on the TV. It was so terrible it was good read more

Well I only went here one time and let me just say this... if you are black they dont want you here.... I was asked for my vaccine card and thought i had it but couldn't find it... meanwhile two other men walked in and one was identified as regular but the other was his new comer friend which he said he had never been there before outright upon walking in, immediately served. No questions about vaccine cards or anything. I guess the woman behind the bar prefers men as customers because i never stood a chance. I'm black and there were no other black people in the bar. Enough said. I have only lived over here for 2 weeks, but I have gotten similar greetings at other bars, whether i was turned down at the door or not. Black people are not welcomed up north in Chicago. It's very disappointing. read more

Small local bar about 10 seats. You can use the juke box and play pool. Very limited beer selection. Mostly a usuals bar. The music stops when strangers walk in but the cheers continue quickly after that. read more

Teddy Bear Lounge - a pint of beer on the bar - Dive Bars Near Me - Chicago, Illinois

Teddy bear is a wonderful place. Not just for old men. This is a really great place that invites the best of the neighborhood and is welcoming with open arms. I've been to a ton of bars in the city as well as Avondale, but cannot think of a more inviting place than Big Teddy Bear. If you're looking for drama; leave it at the door. If you just want a cool place to chill out and meet the real Avondale; then this is the place for you. read more

The middle-age dominated group at happy hour is a riot- health conscious men drinking "pink lady," the women drinking miller lite, all singing along to Belafonte or oldies on the jukebox even if the songs are an octave out of range. Based on the good-natured ribbing between customers, the regulars go way back. The ambiance is highlighted by fake plastic brick with teddy bears, but I'll be forgiving here- this is probably the only bar in Jackowo I'd feel comfortable recommending to a woman drinking on her own- not that you'd be ignored here, but it is all around safe and friendly. Sure, the crowd is a bit older than the Yelp mainstream, but don't we all need a break from self-consciousness and taking our jobs/dating lives/image too seriously? This is the second-to-last Avondale bar for me to review on Yelp (not counting the two unlisted dives for which I respect the owners' wishes to remain anonymous). It also turns out to be one of the best. The reason I didn't find this place sooner is that it's in the distant reaches of Avondale in an industrial section of Pulaski. It's a good two mile walk for the Yelpsters concentrated in south central Avondale, just far enough to burn off the calories of a couple of $1.50 Old Style drafts and call the day a wash in terms of physical fitness. read more

To put simply..."a hole in the wall" To be a little more descriptive, a nice little place to go to where it isnt too loud...too classy...or too expensive to drink! I went there for the first time this past wednesday and upon arriving @8pm, the entire bar turns to watch you as you enter! Yeah, the place is obviously not that big and has your typical wood paneling and laminent tile found @ an old school dive bar. The people around the bar seemed to be "regulars" as they all chatted amongst themselves. My buds and I sat @ a few tables on the outside and were amazed when we heard $1.50 Old Style drafts!!!!! After putting a bunch back, the owner even came by and bought us a round on her. Very cool... Bartender was also a nice addition to this scenerio. She was an attractive young woman wearing that was very sweet and introduced herself to everyone as we sat @ the bar later on. The place was a nice starting point or ending point for sure, but dont think i would be able to stick around ALL night there. Defintely a 'fan' for what it is... read more

Was on my way to Brudder's to catch one of the Cubs playoff games and as I parked in front of this lounge the name got me. Teddy Bear Lounge??? I was curious. Walked in and my curiosity was satisfied. The moment we walked in EVERYONE (which was mostly older white men) turned their whole body out of their seats to look at us. AWkwarddddddddd. The waitress (Anya??) was super sweet and she even came from behind the bar to introduce herself and shake our hand. I thought that was super nice. None of their beer is more than $2.75, because they only have High Life, O'Douls and some other domestic beer. Glad I went in, probably won't come back in. read more

A special gem on the Northwest Side. It doesn't get friendly than this! Great prices on drinks - updated and very clean! read more

I'm not a regular but I do stop in. I live really close. Sitting here buying other people drinks and my own while tipping every round I guess is not appreciated. Other got a Shot with the bartender while I sit and just watch. I'm sure I drank and tipped more and played pool n jukebox. No appreciation. I will never return on Sunday evening... It's the little things that count read more

This is a place for old dudes with big fat city pensions to come in and talk to pretty bartenders buying them shots. I couldn't beleive how much the blond Polish bartender was drinking and this place seemed a bit dirty. nonetheless, it is what it is and it is a dive. A kind of bar with kind of people you would of found all over the city decades ago. read more

This is a classic Chicago watering hole. You've never been here? You might get stared at when you walk in. It's small. Lots of day drinking here for Cubs/Sox games. Have some fun! read more

Stella & Wally are the best.They will go out of their way to make you feel comfortable and make sure you have the right drinks.Best dive bar on NW side. read more

Best bar in the world! Great service no matter who the bartender is! Very affordable prices and super clean.

This is a bare bones dive bar. Great prices, nice bartenders (Kate was my bartender) standard jukebox and mini pool table. No sign. Always stays open til 2. read more

There are too few places like The Teddy Bear left in Chicago. Like any well run business, it is ownership that makes the difference. Stella has owned this place for over 20 years. She is incredibly generous to her clientele (long-timers and newcomers alike) and hires beautiful women who have personality to burn! It is always clean, reasonably priced and, believe it or not, full of people that watch out for each other. If someone is out of line, they'll hear about it from the bartender and the regulars. Have always loved the Teddy Bear. Always will as long as Stella is the owner. On an out of the way stretch of Pulaski Road on the "real" northwest side, you'll find a gem when you stop in The Teddy Bear. read more

Great Bar with great people on both sides of the bar. The owner, Stella is there during the daytime, and is very adept at making you feel instantly welcome. Prices are fantastic, the beer is ice cold and the regulars are the nicest group of people you could ever hope to meet. The Teddy Bear is now one of my go to spots. read more