Something Fun to Do in Chicago on Sunday?
February 25, 2013 3:38 PM   Subscribe

What's a good place in Chicago to take 5-7 people in their early 20s for dinner/some sort of entertainment on Sunday? Note that not all are over 21.

Should be:
-In the loop or only a couple of el stops away.
-Under $35/person including dinner
-Involve some sort of low-key entertainment like live music. Nothing that would require people to participate or that might be out of their comfort zones.

The individuals in question are all strangers to me and each other, some are possibly foreign, and all are probably nerdy. We're trying to recruit these people to live here, so it should be something that shows off Chicago as an attractive place to live, but nothing potentially alienating.
posted by matildatakesovertheworld to Travel & Transportation around Chicago, IL (12 answers total) 2 users marked this as a favorite
This is a cool Irish pub in the Lincoln Square neighborhood.
Its about 5 stops from downtown but "Chicago" isn't really in the Loop anyway.
This is a lively, fun area for shopping, walking, movie going, and the like. They have Irish music sessions every Sunday at 5 PM. The food is good. Everybody likes Irish music, don't they?
posted by Tullyogallaghan at 5:48 PM on February 25, 2013 [1 favorite]

The Grafton is great. Honesty, I think you're going to have a tough time finding what you're looking for in the Loop or very nearby. Those areas aren't really made for cheap, low-key fun.

Picking a neighborhood and sticking there for dinner and a drink would work. Logan Square has tons of great restaurants and The Whistler, Quenchers, and Township have live music most Saturday nights. Andersonville would work for this too: dinner and then drinks at Simons or Hopleaf.
posted by anotheraccount at 5:56 PM on February 25, 2013 [1 favorite]

For morning or just after noon:
House of Blues' Gospel Brunch, held at 2 times on Sunday. House of Blues is just north of the Loop, still within the "Downtown" region.

Or for something in the evening, there is Buddy Guy's Legends, also very close to the Loop. There is a free Jazz thing in the early evening, or a $10 cover if you go for the evening blues session. They do serve food, you can check out their menu online too.
posted by Anwan at 5:59 PM on February 25, 2013 [2 favorites]

To reiterate whatever we do must be open to those under 21.

And unfortunately, they're staying in the loop and will likely be tired, so it does need to be close by. But the under 21 thing is non-negotiable.
posted by matildatakesovertheworld at 6:16 PM on February 25, 2013

Oh and I'm definitely open to non-live music suggestions, that was just the first thing that came to mind.
posted by matildatakesovertheworld at 6:18 PM on February 25, 2013

I have a couple more questions for you:

* What brings this group of people together specifically? I thought for a second post-doc/academic recruiting, but that wouldn't explain the youngsters.
* Is the $35/person being paid out by an organization, or is this money that each of these visitors is going to be expected to pay? I ask because if it's an organization paying, maybe you could rent a minivan with some of the money and that would open up a lot more of the city.
* Are you trying to wow them, or show them things that the locals actually do on a regular basis?
* Can you tell us what hotel, or what part of downtown their hotel is in? If you've got to make every transit minute count, it makes a difference whether you're in the Mag Mile or the South Loop.

This is my opinion and I may be alone in it, but as a nerdy introvert I would hate to go to live music with 5-7 strangers. Especially live music that I didn't choose. Usually it's loud so you can't talk but you're expected to dance, otherwise you'll be standing there looking awkward. I'd be outside my comfort zone--maybe others wouldn't, but you mentioned wanting to make folks comfortable.

Unfortunately cheap, interesting, low-key entertainment doesn't really exist in the Loop. I love Lincoln Square and the Grafton, Simon's, and Hopleaf, but they're pretty far from downtown. Depending on which train line you take, it's about 10-13 stops + walking, or approximately 45 minutes - 1 hour one way to get to any of those places from downtown. (I just saw that you live in Chicago, so you may already know this.)

I would say a better bet would be Wicker Park, which is off the blue line and closer to downtown. Right off the Division blue line stop is Podhalanka, a Polish restaurant. It looks like someone's basement, but the food is delicious and cheap.

After that, you might take people up Milwaukee Avenue to North Avenue (15 minute walk), and maybe take them to look at comics and art books at Quimby's or used books at Myopic. Myopic is open late, but Quimby's and Podhalanka close around 7 pm on Sunday.

On the way to the bookstores you'll see a lot of Wicker Park and the bars and nightlife and hipsters. Depending on how ambitious you're feeling, you could get dessert with these folks somewhere nearby. I LOVE Hot Chocolate, which is further up Damen, but that's another 15 minute walk from the intersection of Damen and Milwaukee. The desserts are amazing and it's worth the walk even in a Chicago winter, but it may be too much for people who don't know what they're in for. There's a make-your-own-ice-cream-with-liquid-nitrogen place right on North Avenue, iCream, that is novel in a science-y kind of way.

Also, have these guests been properly informed/warned about what they need to be wearing for a Chicago winter?
posted by Colonel_Chappy at 7:12 PM on February 25, 2013 [2 favorites]

Hot Chocolate is super-hyped, and it somehow manages to be even awesomer than you expect. It is amazingly great and fun.

My Chicagoan brother says:
This sounds like a lost cause. If they're staying in the Loop and don't want to go out of their way, they won't see Chicago.

[He used to live in Lincoln Square, and we've enjoyed the Grafton multiple times. I'll add that the bus is easy to take, too -- there's a TON of stuff along Halsted that is really easy to find.]

Publican's good. Lots of meat. Little goat you can get in and out of for under 35/person.

Honky tonk has live music and bbq.
posted by Madamina at 7:38 PM on February 25, 2013 [2 favorites]

$35 for entertainment and dinner and they don't want to leave the Loop? It's a tough one. Maybe just dinner and a walk around Millennium Park or up Magnificent Mile.

The Second City is only a few stops on the Brown Line. They have a Sunday matinee that's geared towards out-of-towners. However, humor doesn't always translate well across cultures and if someone's English isn't too strong they're going to feel left out. Old Town has some decent restaurants.

The Art Institute has a new "Picasso and Chicago" show that I hear is really good.

There is a matinee performance of Schubert music for solo piano at Symphony Center.

The Pat Martino Trio will be at Jazz Showcase. I can't tell if it's 21+, but you could call.

If they're going to be tired, I suppose a walking architectural tour is out.

I love Quimby's, but it's going to be outside of a lot of people's comfort zones.
posted by hydrophonic at 8:04 PM on February 25, 2013 [1 favorite]

If there are several of you I highly recommend splitting a cab to get out of the Loop. The Loop is definitely not the best of Chicago.
posted by walla at 1:10 PM on February 26, 2013

If you really have to stay in the Loop and they're tired and hungry, why not just take everyone for dinner and conversation at a Chicago-style pizza place? Not the most adventurous thing to do, but it's signature Chicago and a foodstuff that foreign visitors may find fascinating. Gino's East is my personal favorite, but Pizzerias Uno and Due are good too. There's usually a longer wait at the latter two, though.

The Art Institute suggestion is a good one and there's Pizano's that serves Chicago-style pizza right down the street.
posted by Colonel_Chappy at 6:27 PM on February 26, 2013

We've been explicitly asked to do something beyond just dinner and to show them a little bit of the city. However, they have to get up pretty early the next morning and we can't start too early in the afternoon, hence not straying too far from the loop. And trust me, we're just as frustrated by these constraints.

Our current plan is to walk over to Millennium Park and the Bean, pop into the Cultural Center, walk up Michigan Ave (pausing at the Tribune building) and then walk over to dinner at Iberico's. It's a lot of time outdoors but they'll be warned ahead of time so hopefully will be prepared.
posted by matildatakesovertheworld at 6:43 PM on February 26, 2013

pop into the Cultural Center

Good idea. Shawn Decker's Prairie is fantastic. There's a dance performance there this Sunday.
posted by hydrophonic at 7:41 PM on February 26, 2013

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