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Pioneer Lounge

5.0 (2 reviews)
Closed • 6:00 pm - 2:00 am (Next day)

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1 month ago

Very friendly and accommodating staff. Cold drinks. Local. Neighborhood. Old history.

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7 years ago

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Jefferson Inn

Jefferson Inn

4.3
(34 reviews)
3.1 mi
•$

So I been here once before with a friend I ran into had a great experience the bartender was very…read morenice and very attentive and I actually met some cool new friends who I still talk to . This time I decided to go in right around 1 am and I was only planning on staying for about 15 min because I was waiting for a friend to pick me up at the train station across the street so I wanted to kill time i know that they were open bc I saw the manager (shorter guy black hair )come out with a beer in his hand and drink it in front of the business while talking on the phone loudly. When I walked up to the door it was locked and the bartender looked confused .. so I tried to call them on their phone and they both. Looked at me as if I'm committing some type of crime because I was asking them why I couldn't come inside . They both told me to fuck off and kept the door locked . Extremely unprofessional . The manager could have Atleast came up to me and made up something to not be rude but he didn't even bother doing that . The bartender looked confused but I only put 5 stars so they could see this . You guys are ridiculous.... Idk about ever coming back again and I'll be letting everyone know about this . I never been locked out of a bar in my life and i dont think I'll be referring anyone to stop at this place ever again. unprofessional. hope u lose all ur business

My daughter lives in Jefferson Park and I visit her a lot from Florida, enjoying all her…read moreneighborhood bars. Jefferson Inn is right up there at the top. Great bartender. Great beers. Dive bar atmosphere. I will definitely come here again the next time we visit.

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Jefferson Inn.4874 N Milwaukee Ave, Chicago, IL Cool!
Jefferson Inn.4874 N Milwaukee Ave, Chicago, IL Cool!
Jefferson Inn.4874 N Milwaukee Ave, Chicago, IL Cool!
Jefferson Inn.4874 N Milwaukee Ave, Chicago, IL Cool!
Jefferson Inn.4874 N Milwaukee Ave, Chicago, IL Cool!

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Jefferson Inn.4874 N Milwaukee Ave, Chicago, IL Cool!
Teddy Bear Lounge

Teddy Bear Lounge

4.2
(23 reviews)
2.3 mi
•$

I lived in the area from 2008-2009 and found this place one night, loved it and frequented it…read moreoften. 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

Really cool neighborhood dive bar. Very clean. Fun decor and art work. I appreciated the Prince…read morepainting. 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.

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Teddy Bear Lounge
Teddy Bear Lounge
Teddy Bear Lounge

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Pioneer Lounge - sportsbars - Updated July 2026

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