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Help: three nights in Chicago, three very different dinners

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Mrs. Machaca and I will be in Chicago next week -- we need to plan Thursday, Friday, Saturday dinners, with different requirements for each.

Thursday is just me and Mrs. M, willing to spend for a great meal. If Alinea hadn't been booked, we'd go there. Reading posts here, we were considering Avenues, Moto, maybe Blackbird on the more casual end. Is Moto worth doing if you don't spend 7 hours there? Are they receptive to dietary resrictions? (My wife is vegetarian + fish.) Same questions for Avenues since I'd probably want the tasting menu there.

Friday is with friends from work, will try to keep the price a little more reasonable. Thinking of Avec if we don't go to Blackbird the night before, or Green Zebra, or Cafe Spiaggia.

Saturday is with Baby Machaca and Machaca-in-law. Good night for some casual but great chow in a place where we can eat early, relatively quickly, and with a baby. My wife's meeting is at the Chicago Hilton (720 S. Michigan) so something walkable from there would be great. (The other nights we should be able to get in the car, but nearer is a bonus.)

All suggestions very welcome (i.e. don't restrict yourself to the places I listed above, that's just what I gleaned from reading a lot on this board!)

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  1. I'd hop on the phone and start making reservtions now. Some of the places you mention book up weeks in advance.

    I've never been there, but I've seen mixed reviews about Moto. The food seems to be a little over-conceptualized.

    I like Avec. The bacon wrapped dates stick in my mind. A favorite of mine for Friday might be Coco Pazzo - Italian. In fact, I was there tonight. The Stracci pasta dish is delicious - hand made pasta with mushrooms, asparagus, garlic, and white truffle oil topped with shaved paremesan.

    I also keep harping on about May Street Market on west Grand ave. I've had a couple of great meals there. Its a little out of the way - 10-15 min cab ride from the loop.

    1. For your splurge meal, I'd add Tru to the list. They do a nice multicourse vegetarian meal (seafood "collection" dinner is also great) and they are great when dealing with dietary restrictions. Avenues would also be a good choice. I was extremely disappointed by Moto--I have nothing "weird science" cooking as long as the food actually tastes good, which was not the case with more than 50% of what I ate at Moto.

      Green Zebra, Blackbird and Avec are great choices. Cafe Spiaggia is excellent, albeit rather expensive for a casual place. I had a flawless meal at Topolobampo last week and they have a number of excellent vegetarian options. The ceviches and oysters are excellent, too.

      1. A good solution for Saturday night would be Hackney's Printers Row, practically around the corner from the Hilton. Very casual, family-friendly, top-notch hamburgers but also some good salads and usually a tasty advocado/cheese sandwich. It gets lively on a Saturday, but if you're there early you shouldn't have a problem getting seated. Here's their site:

        http://www.hackneysprintersrow.net/

        And afterwards, stop by at Canady/Chocolatier for some pistachio gelato (824 S Wabash Ave).

        1. I'd add Custom House for either Thursday or Friday - same folks as Green Zebra, and in south loop so close to your hotel.

          For Saturday with the bambino, I'd recommend Wishbone (1001 W Washington). It would be a short cab ride from your hotel. It's a Chicago brunch institution, but I have found dinner is also excellent and less crowded.

          1. Vegetarian + Fish? for Thursday night I'd suggest Arun's. Maybe the best Thai restaurant in the world! and NOT cheap like most folks are accustomed to thinking of Thai. This is definitely FINE dining!

            1. Thanks so much for the help, everybody! I will try to write a long report in the next few days. But to settle any suspense -- we went to Avenues for our splurge, Green Zebra for our night out with friends, and Orange for meal with baby (which turned out to be a brunch.) I have great things to say about all three!

              1. The Exchequer handles babies and small children quite well and is a pretty typical (and inexpensive) Chicago pub about three blocks north of the Chicago Hilton on South Wabash.

                Accross from the Hilton on South Wabash is Thai Spoon, a local student favorite, which serves pretty good Thai cuisine.