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Please please please help a desperate chowhound bride make a decision soon!

Hey guys,
My name is Leena, and I am addicted to food. I love reading, writing, watching and eating food in any form. While I really wanted a chowhound-worthy wedding, lack of funds have forced me to use the preset caterer for the wedding hall I am using, and I have no clue how good the food will be. So, as a present to myself and my wedding party, we decided to take out the entire wedding party and their dates out to eat the day after our wedding so we can all spend some quality time together and eat some good food.
We wanted to go to a BYOB, that way, we could afford a great meal and bring wine for everyone, thus covering all the charges for the evening. We have a reservation set at HB, but it is such a small place that our large party (21 people total) cannot sit together. So now we are left with another decision to make. We either need to a) find another BYOB chowhound worthy
b)find a regular restaurant chowhound worthy and have them buy their drinks
c) use one of the half priced gift cards from q101.com for the restaurant (you pay $25 for a $50 gift card to one of the following restaurants: Chicago Firehouse, Cuatro, Bordo's Eatery) and again have them buy their drinks
d)stick with HB and just deal

We would like the food to be good, and we hope to get away with spending $50/a person(at least three courses), not including drinks, if possible, we would like to all sit together. So does anyone have any opinions on what we should do? Should we stick with HB and not all sit together? Should we head to another BYOB and if so, which one do you reccomend? Finally, do we scrap the whole BYOB deal, find a decent place that can do $50 a person, and have the wedding party buy their own drinks (which they would have no problem doing)?
We have to make a decision and reservation asap, because the wedding is on Oct. 6th. I really appreciate anyone even reading this, so thank you and help out if you can!!

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  1. (What's HB?)

    I recommend a restaurant in Greektown. Costa's and Santorini are the high-end while Parthenon and Greek Islands are reliable. All have broad menus which will provide good grub over three courses (e.g., cold appetizer plate, zucchini with skordalia, Greek salad, octopus, lamb-chicken-fish-pork entrees). Greektown restaurants are unsurpassed in handling large groups, and the middle-range places like Parthenon and GI are already noisy, so your group can revel. I don't think the Greek wines at these places are rip-offs, either, so keep ordering 'em by the jug.

    After dinner you could segue to Artopolis, the hip cafe-bar-bakery south of Parthenon, and maybe take over the upper level for drinks and a wide choice of desserts, some not strictly Greek.

    Have a great time. Greetings from JJC and The Herald News (right?).

    1. I am assuming that HB is the Hearty Boys Cafe in Boystown. If you want to stick in that general area, I would try Riques Regional. ( http://www.riqueschicago.com/). I know I sound like a broken record and I swear I'm not affliated with them. The food is good, it's relatively cheap, it's BYOB and it's a small business and the owner/chef really cares about the food. The have a party room apart from the general restuarant. If you don't want that, then I second the req for Greek town

      1. Greektown is a great choice. The food is high quality and prices reasonably...plus the restuarants cater to large groups for all occasions on a daily basis. Wine is reasonable as well.
        I think that Greek Islands consistently has the best food. Everything on the menu is delicious. The atmosphere is vibrant and the parking is free. Santorini is a bit more upscale and excellent as well.

        Andalous Morrocan in Wrigleyville is BYOB.

        Cafe Iberico could be a lot of fun and priced right! Pitchers of Sangria are reasonably priced and will surely please your guests.

        Wildfire, Cafe Babareeba, & Scoozi would all fall within the $50 per person range.

        1. Two points.

          As far as seating all together at HB, IMHO, once you have more than 8 people at one table, you're not really sitting together anyway. It seems like having two of three smaller groups in the same area would be fine, especially if you circulate a bit.
          I second Cafe Iberico for a large group (there it would be one long table). You would be hard pressed to get out of there with empty pockets, given your budget. Sangria is great and tapas whirling out every few minutes makes for a festive evening, and it is cheap, cheap, cheap.
          Good luck.

          1 Reply
          1. re: malone

            True about the table comment, however, in a restaurant as small as HB, we would not be able to toast our pals, or even visit as we may like without disturbing fellow patrons. I know I put a lot of restrictions on the suggestions, but I just want to see what is out there before I decide to settle, you know?

          2. I second the Riques recommendation. A friend had his birthday in their party room last fall and it was wonderful. They set up one big table that seated about 20 or so, and even provided us with a waiter to serve the drinks we brought.