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Help planning ONE evening in chicago

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So my girl and I (both young 20s) are coming to Chicago from NY for one evening. I was hoping I could get your advice on putting together something.

We aren't so much into $150 dinners at celebrity chef restaurants or places with white table cloths. In NY, you are more likely to find us deep in the LES and as far away from Meatpacking as possible. I'm thinking grabbing a cocktail some place hip/snazzy (Violet Hour?) pre-dinner, good dinner, dessert some place else, and then a happening bar/club for people watching/dancing. Ideally, all of this could happen in one neighborhood so we don't have to trek all over Chicago.

I know some of you out there must have that "killer" first date completely planned out. Please share! I'd be happy to do the same for you in NY. (For example, dinner at Little Giant, drinks at East Side Company Bar, and dessert at Chocolate Bar, followed by dancing/people watching at Von). Thanks in advance, I really appreciate it.

We are going to be in town October 10th, if there is something exciting happening that day.

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  1. Since you threw out Violet Hour (which I love, by the way) I took a stab at throwing out some suggestions in the Bucktown/Wicker Park area, all of which should be reasonable walking distance to each other.

    Dinner -
    Spring - pretty elegant, with good food, and this is the pricier of the two ideas I have here. It has been a long time since I have eaten here, but I really liked my meal. It's seafood-focused.
    http://www.springrestaurant.net/

    Mado - more casual, with the whole exposed brick/chalkboard menu thing going on. I had a really enjoyable meal here - most things are sized so they're shareable, and it was still BYOB. You might want to call ahead to see if they're still BYOB.
    http://www.madorestaurantchicago.com/

    Dessert -
    Hot Chocolate - I have never been, but this is a popular spot in the neighborhood for dessert!
    http://www.hotchocolatechicago.com/

    Post dessert people watching -
    Chaise Lounge has a nice outdoor area that I've enjoyed for people watching, but there's not anything in the way of dancing.
    There's a ton going on in the neighborhood, so I have a chance you won't have trouble just walking around and finding a place to pop into.

    Happy visiting!

    4 Replies
    1. re: jn2001

      I agree, Violet Hour is cool. Be prepared to wait to get in on a weekend though. VH is in Bucktown/Wicker Park which is where I live and IMO the coolest hood in Chicago. I love Bluebird, a few blocks north on Damen from Violet Hour for dinner. They do the artisinal cheese and meat thing with a fantastic wine and beer list. Next door to Bluebird is Hot Chocolate which is also great for dinner but fantastic for desert. Also, not far from VH is People Lounge, a cool tapas place with a DJ that I have always enjoyed.

      1. re: kellyinchi

        Kelly, Is Wicker Park the only neighborhood you've lived in? I'll agree with you that it's a hip place, filled with great restaurants and bars today but you and 90% of your neighbors probably didn't live there 15 years ago.

        That's besides the point. Since there is a Wicker Park thing going here and I've been into tequila for too many days on end, I recommend Salud, just south of North Ave on Milwaukee.

        FYI Eric - Wicker Park is easy to get to. Blue Line towards OHare, Damen Stop. You're in the thick of it. And pardon my shot at Kelly - she's right, Wicker Park is a damn good time.

      2. re: jn2001

        Thanks for the advice, sounds great! Violet hour for pre-dinner, spring for dinner, hot chocolate for dessert, and either second city/signature room/nacional 27 for after dessert, depending how the lovely lady is feeling. appreciate the advice. one random question: can you hail cabs on the street in chicago?

        1. re: ericmorrow

          yes you can. and if you want to get one in advance call 1-800-taxi-cab. they'll connect to you flash cab