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    Oskar

    4.7 (3 reviews)
    Open 5:00 pm - 10:00 PM

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    10 months ago

    Helpful 4
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    2 months ago

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    7 months ago

    What a gem! Just the right size to feel cozy. Top-notch service and drinks. Indoor and outdoor seating available seasonally.

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    Ward Eight - Taylor Small Batch whiskey

    Ward Eight

    (246 reviews)

    $$

    Ward Eight was a place we frequently visited when we lived nearby many years ago. We were in the…read morearea recently and decided to stop by...we discovered this gem from our past has only gotten better! High quality and innovative cocktails, reasonable prices, and a chic/classy ambiance make Ward Eight must-visit! I tried two cocktails when I was at Ward 8: Remember the Main and Vieux Carre. Both were decadent, delicious, and boozy. Triple threats! I loved them both, but the "Remember the Main" was different from drinks I've had before, so that was my favorite. My husband had a local beer. They have beer, wine, and NA options for folks who aren't into cocktails. They also have food which looks scrumptious, ranging from high-end appetizers to full meals. We did not come prepared to eat, so we'll have to come back again to try food in the future! The staff were welcoming and professional. The space was clean and Gatsby-style chic. There is plenty of seating and an outdoor space for when it is warmer. It is a fancier places, so prices are higher. But you pay for the higher quality ingredients and innovative recipes. If you enjoy cocktails and cozy cocktail bars, Ward Eight is definitely the spot for you!

    Cocktail was neither worst nor the best rendition of a Vieux carre that I've had. I've said it…read moreseveral times that many things that originate in New Orleans are hard to replicate outside New f the big easy. I got the feeling that the staff were putting some effort into their craft. The place was crowded & there was even a live band performing. The bar had some above average bottles such as Hibiki & Bookers. I was pressed for time but there were at least three more menu items I would've tried.

    Barrelman Tavern - Our pups love to hang out at The Barrelman!

    Barrelman Tavern

    (74 reviews)

    $$

    Edgewater

    Nice little neighborhood beer bar. Good selection of beer and liquors. I was in the hood and…read moreneeded a place to watch the Bulls game. This popped up and it hit the spot. Chill crowd, friendly bartender, clean bathroom. I wouldn't seek this place out, but if I'm in the area I'm happy to stop by. No food that I can. Maybe the biggest downside.

    Very chilled little bar in a weird location on Peterson, about a block west of Clark Street…read more Barrelman is located on the short stretch of Peterson that is between Clark and Ridge. If you are like me, trying to make that light, you will never see this place, but it is there and it is super cute. There is a lot of dark wood that just gives the space a cozy feel. There are also two garage doors that I assume can be opened when the weather is good. For you folks with dogs, beer drinkers who drink beyond the basic beers, bubble drinkers (like me) and those that want to bring in their own food...this is your place. We went there to meet some friends and to watch some football. For such a small place, they do have plenty of TVs with multiple games going. It was great to be able to have pizza delivered, with the bartender providing paper plates, and napkins for us to use. The bartender was also very cool about bringing our drinks over or picking up empties as we were sitting a a table away from the bar. I didn't get his name, but he was cool. There is street parking but not on Peterson itself. I would say, depending on the day, it might be hard to find a spot as you have to park on Ridge or some of the side streets. There is a new Metra station down the street that is about 2 blocks from the bar. Not sure if there is public parking available, but worth checking out. I could see myself coming here just because I can bring my own food and still get bubbles. While they do not carry bubbles by the bottle, the stuff they had in the can was good. I would love to go there when the weather is nicer and they have the garage doors open. And it is a happy compromise to hanging out with friends who have dogs that they just can't live without who also like to drink. This is a place we can definitely hang out with them and have a good time.

    Little Bad Wolf - Bad Burger and a side of mac and cheese

    Little Bad Wolf

    (2.6k reviews)

    $$

    Andersonville, Edgewater

    There's just something about a burger that actually lives up to the hype--and Little Bad Wolf does…read moreexactly that. Stacked unapologetically high, this burger is everything you want and more: juicy, perfectly seared patties layered with melty cheese, crispy bacon, and those golden, crunchy fried onions that take it completely over the top. Every bite is rich, savory, and just messy enough to remind you you're eating something seriously good. The toasted bun somehow holds it all together (barely), soaking up every bit of flavor without getting lost in the chaos. And then... the shoestring fries. Thin, crispy, golden perfection--light but addictive, with that ideal crunch that makes it impossible to stop at just one (or ten). They're the kind of fries you keep reaching for without even realizing it, especially dipped in that creamy, tangy sauce on the side. And let's not forget the drinks--just as good as the food. Refreshing, perfectly balanced, and the kind you sip slow while taking it all in (but somehow they disappear way too fast). It's not just a burger--it's one of Chicago's most iconic bites for a reason. Bold, indulgent, and absolutely worth every single napkin you'll need after. The ambiance inside is GORGEOUS!

    My husband and I walked in on a Sunday evening for dinner and were able to be seated right away…read more The atmosphere is dark and moody, and it made sense once I realized it was the same owners as Gretel. Loved the 90s female R&B playlist they had going! Little Bad Wolf has been on my list FOR YEARS to try the burger! My husband got the burger with fried onions and I got some Bao because those also looked delicious and were a popular menu item. Honestly the 3 stars are only that high because of the service. Our server was friendly and attentive + the food came out hot and quick. Unfortunately, the food was pretty disappointing. The burger was swimming in a puddle of grease and just picking it up made your hands greasy + was dripping grease. The fries that came with it were floppy, soggy, and sad...but at least warm? I personally wouldn't order this again. The Bao were better, but small for the price and honestly were just okay? It was nice they gave you sauces you could add, but I found the Bao's to already have enough sauce so I didn't need them. Overall I left feeling confused and disappointed. I don't feel the need to come back here - Little Bad Will was a one and done experience for me.

    Maize + Mash - Seafood Gumbo

    Maize + Mash

    (520 reviews)

    $$$

    I had a really good experience at Maize & Mash. The food absolutely lived up to the hype!…read morephenomenal, hearty, and very filling. No complaints at all on that front. The atmosphere leans more toward a cocktail bar or speakeasy vibe. It's darker, loud, and energetic, which gives it more of a bar feel than a traditional sit-down restaurant. That said, the food quality is outstanding for that type of environment. Their cocktail menu also looked incredible, with what seemed like endless options no matter your preference. The only downside was the wait. I had a 7:00 reservation, but our table wasn't ready and we ended up waiting about 10 minutes. During that time, several DoorDash and Uber Eats drivers came in and out picking up orders, which just reinforced how popular the place is. Overall, this place is clearly in high demand and delivers amazing food. Just go in knowing it's more of a lively bar atmosphere than a quiet dining experience.

    If you want an intimate date night spot for quiet conversation, I wouldn't recommend. It's…read moredefinitely more of a bar scene, but upscale. The food is very hearty and comforting. The potions will make you extremely full. The food isn't typical bar food. It's definitely a mix of upscale food with a louder bar environment. Would definitely go for the food again, but would probably only grab a drink in the restaurant. When we got there it was a bit chaotic with no sign to wait to be seated or seat yourself. The hostesses were running around and finally 10 minutes after our reservation time were we seated. I definitely recommend the food, and if you're up for a good drink at a bar I would say definitely try it out!

    Oskar - whiskeybars - Updated May 2026

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