Hip Chicago bar for mom to meet boyfriend at

November 8, 2011 6:59 PM

*CHICAGO FILTER* My shy, relatively new boyfriend  is meeting my mom for the first time while she is in town. Whats a low key hip spot to go for  dinner & drinks.

I'm not really worried about it being that weird as my mom is super cool, I'm just having a hard time finding a place to go. I would like to avoid extremely touristy places and  nothing way too fancy. Also, the louder the better to avoid potential awkward silence.
Any type of food is fine as long as they have a decent drink menu. I'm new to the Chicago area and want to pick a more "locals only" kinda place!
I'd prefer a place that takes reservations, too!
Thanks guys! 
 (possibly unnecessary background info: we're in our 20s, try to be trendy, both more "artsy" types. Haha)

posted by twoforty5am to food & drink (24 answers total)

What's your budget?
posted by phunniemee at 7:01 PM on November 8, 2011

I know nothing about Chicago, and actually clicked on this by accident, but can I make one gentle suggestion? "The louder the better" can really bite you on this kind of thing. Having to say "What? Could you repeat that?" to your girlfriend's mom is mortifying, as is smiling and nodding and saying "yep!" and hoping you heard her right and she was saying "Have you tried the glazed duck?" and not "So, you and my daughter fuck?"
posted by Tomorrowful at 7:06 PM on November 8, 2011 [3 favorites]

Haha good call!
Thank you!

Also, I apologize for my horrible grammar in the first post. Typed it on the iPhone while on the train...
posted by twoforty5am at 7:16 PM on November 8, 2011

The Paramount Room is good.
posted by phunniemee at 7:21 PM on November 8, 2011

Hot Chocolate (in Bucktown) was my first thought. There's always a lot of activity to fill awkward silences or provide conversation starters. I wouldn't say it's loud, but it sure isn't moribund. It's owned by a pretty well known pastry chef but the food is actually better than the desserts. The mussels were fabulous, and the macaroni and cheese just cries out for sharing.
posted by DrGail at 7:30 PM on November 8, 2011 [1 favorite]

Hmmm... low-key AND loud? Huh. Also, you're not really specifying the location, so you'll have to figure that out.

The Grafton in Lincoln Square might fit the bill, especially if it's got live music that night.

The Orbit Room has very tasty food, including mac and cheese.

We had a great dinner at La Madia a couple months ago. It looks super hip, but it was very comfortable.
posted by Madamina at 7:44 PM on November 8, 2011

The California Clipper is a hip retro spot with delicious drinks and intimate booths that are excellent for conversation. It's usually a pretty low-key, nerdy crowd unless they're having a swing dancing event.
posted by Lieber Frau at 7:47 PM on November 8, 2011

What neighborhood do you live in? If you want to be truly local, you should find a place within walking distance of your building. Avoid downtown and popular tourist neighborhoods like Lakeview and Lincoln Park.
posted by tully_monster at 7:48 PM on November 8, 2011 [1 favorite]

I really like Hopleaf at Foster and Clark.

Seconding the Grafton, but it's not really "hip".

If you want loud, go to Cafe Iberico, though drinkwise you are limited to wine, sangria, or a limited selection of beers.
posted by baniak at 7:54 PM on November 8, 2011 [1 favorite]

I go to Mana on Division for these sorts of things. It's middle end vegetarian tapas, so you get to burn awkward conversation discussing what to order. Nice but not fancy. And they have great drinks too. No reservations, but if you call while you're on your way, they'll hold a table. I've never had to wait more than 5-10 minutes.

I also think Rodan works, but the menu isn't as deep and it can be a drag depending on the night of the week.

I would also back the Paramount Room and the Hopleaf though I think both fall on the louder side of things.
posted by dvrnvn at 8:02 PM on November 8, 2011

Hard to get seats at Hopleaf, FYI. Even on weeknights. It's definitely amazing and impressive, though.
posted by Lieber Frau at 8:46 PM on November 8, 2011

Seconding Hot Chocolate. (I think that area is actually Wicker Park, not Bucktown.) Good atmosphere, good desserts.
posted by Mikey-San at 8:50 PM on November 8, 2011

Never seen Hopleaf uncrowded, but that came to mind too. The mention of Wicker Park made me think of The Southern.
posted by cgk at 8:57 PM on November 8, 2011

My Chicagoan roommate thirds Hot Chocolate and also suggests Feast. She says Wicker Park is good in general for the hip, "cozy-crowded" vibe.
posted by rabbitbookworm at 10:02 PM on November 8, 2011 [1 favorite]

I'm a big Hot Chocolate fan, and I love the Hopleaf, though note that it's not the best choice if you want anything other than beer (I have had a friend order an appletini there with no success). If the Hopleaf doesn't work, you could also try Lady Gregory's down the street--good drink choices, quieter, and a locals feel (though I'm not sure about reservations). It's much quieter than the Hopleaf, for what it's worth, expansive, and the food is good. I wouldn't call it hip, though.
posted by carrienation at 2:22 AM on November 9, 2011

Hopleaf has beer, wine and "normal" well drinks - but they have the best selection of beer in Chicago (one girl's humble opinion). They also have mussels that rock, and since it's mussel season that would be my choice.

Also Longman & Eagle, which is delicious or Revolution Brewery.

I wish I could go to any of these places tonight - I miss you Chicago!!!
posted by monkey!knife!fight! at 4:11 AM on November 9, 2011

I was an artsy twentysomething last time I went to Hot Chocolate, and although it was delicious, it didn't strike me as hip. It struck me as targeting the thirty-somethings with office jobs who were taking over Bucktown (and have now taken over most of Wicker Park).

Hop Leaf is amazing and one of my favorite places, but not exactly low key. It's crowded, it's noisy, and there are more than a hundred good options for drinks. Even the food itself--mussels, duck, etc--is sort of difficult.

The Clipper is fun, but if they have food, I'm not sure I'd recommend it. It's a hipster dive.

I'd go to The Handlebar. Unpretentious, easy to get a seat, relaxed atmosphere, good drinks (mostly beer), good food. Easy parking and close to the blue line, too. I recommend the blackened catfish, smoked gouda mac 'n' cheese, green meanie (avocado, pesto & sprout sandwich), or one of the specials, which are usually awesome.
posted by tsmo at 6:47 AM on November 9, 2011

Lula. Or a bit less hip but great parent spot is Dunlays on the square, right around he corner from lulas on Logan square.
posted by Sreiny at 6:58 AM on November 9, 2011

Seconding Cafe Iberico, it is a great spot for this sort of thing. I wouldn't call it hip, but it is definitely delicious. It's also busy in a good way, you feel like you're part of a crowd that's all having a good time. And pertinent to your question, something about sharing tapas makes the conversation flow - you're all eating the same thing so you automatically have a topic in common.

Another tapas place that is a little more hip is Mercat a la Planxa. The cocktails are great, and the decor is modern and interesting. They have entrees as well as tapas, so a little something for everyone.
posted by slmorri at 7:37 AM on November 9, 2011

Nthing Cafe Iberico!
posted by Hop123 at 8:23 AM on November 9, 2011

This is the kind of thing that Cafe Ba Ba Reeba was made for. Technically it's part of the Lettuce Entertain You chain, but it's so great for an occasion like this because there is so much going on around you that if the conversation lulls you'll have something to talk about any way. And YUM.
posted by FlamingBore at 9:36 AM on November 9, 2011

Not sure where you live, but in general I'd pick a Logan Square or Andersonville bar/restaurant over Wicker Park or Lincoln Park. There's some great suggestions above, but I'm thinking those are neighborhoods that have more of a young vibe, aren't terribly expensive or pretentious, and you can get good drinks and decent food. (Longman & Eagle, Revolution are two of my regular spots.) I also think Hopleaf is kind of awkward with food and it's loud and crowded.

And oh! I really like Hop Haus. It's got a kind of "chain" vibe but has great (regular and exotic) burgers and excellent beer and is reasonably priced. The one I go to is extremely far north though.
posted by sm1tten at 4:57 PM on November 9, 2011

This is the kind of thing that Cafe Ba Ba Reeba was made for.

The spicy potatoes at this place are out of sight. Great, chill place for conversation, drinks, and a smattering of stellar food.
posted by Mikey-San at 2:06 AM on November 10, 2011

Another enthusiastic YES for Hot Chocolate! My wife and I came to Chicago to visit her family for Thanksgiving, so I was happy to see this thread. Five of us went to dinner together last night and decided to try Hot Chocolate. It was GREAT! We should have made a reservation, though. We got there about six and they told us the wait was going to be an hour and a half. We ended up eating at the bar and still had a great time. We'll definitely be returning here on future trips...
posted by richmondparker at 6:22 AM on November 24, 2011