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Apr 13, 2014 10:51 AM

Special Dinner In Chicago? Where to go?

At the end of May I am bringing my gf to Chicago for her birthday. I want to take her to a nice restaraunt and could use some suggestions. What are some of the best places that you can think of in the Chicago area? Price is open, so high and low.

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  1. The two best restaurants in Chicago right now are Alinea (considered by many the best in the country) and Grace. Alinea features unusual presentation techniques and fun, in addition to amazingly delicious food; my dinner there was one of the 2-3 best in my entire life. Grace is more traditional luxury, with delicious food along with attentive service. Both will typically cost $300-400 per person including moderate alcohol and tax/tip.

    Another excellent high-end restaurant is Everest, which offers contemporary French cuisine. It's on the 40th floor of the Midwest Stock Exchange Building and the view looking out over the city is exciting. Expect to pay $200-300/pp inclusive, except if you order the three-course fixed pre-theater menu for $50-60 at a 5:00/5:30 seating.

    If you don't want to spend quite that much, or if you want a less formal experience (the previous three places all require/recommend jackets for gentlemen), I recommend North Pond or Naha. Both feature amazingly delicious food from chef-owners who won the James Beard Award for Best Chef Great Lakes. North Pond adds its exquisite setting in the middle of the park, facing its namesake pond, with the city skyline looming over the opposite shore; when making your reservation, ask for seating in the front room with the full-length windows facing the pond. Naha offers a food and service experience comparable to the super-expensive places. At both North Pond and Naha, expect to spend $100-130/pp inclusive.

    All of these places require reservations in advance and I recommend making them as soon as possible. All but Alinea accept reservations on, although I've heard Grace does so only for weeknights, not weekends, so you may need to call them. Reservations for late May should still be relatively easy to obtain right now except at Grace, where weekend seatings have been filling up way in advance but weekdays should still be available. For Alinea you need to purchase tickets in advance on their website, and don't expect a refund if your plans change.

    There are some other high-end restaurants, but these five are my absolute favorites among the high-end group, over all the others. These are the places serving one "wow this is amazingly delicious" dish after another after another, without misses or disappointments in some of the courses.

    If you wanted to spend even less than North Pond and Naha, I could name some other restaurants, but they tend to be casual neighborhood bistro type places, and it sounds like you're looking for more of a special occasion type place. If I'm mistaken and you'd like to hear some of those recommendations, just ask.

    If you're looking for other places to eat while you're here in addition to your special dinner, my favorites which I would consider "do not miss" type places, are Sable (for contemporary cuisine in a small plate format, and craft cocktails), GT Fish & Oyster (for seafood in a small plates format, and craft cocktails), Anteprima (for the best Italian food in the city), Lou Malnati's (for our delicious local specialty of deep-dish pizza), and Jam (for breakfast/brunch).

    All of the above places, except for Anteprima and Jam, are in the downtown neighborhoods or relatively close by. You don't mention where you're staying or how you're getting around. If you need transportation advice or recommendations specific to where you're staying and/or spending time, again, just ask.

    1. Quick question, when you say special, do you mean highest rated, most expensive, television show featured experience meals OR anything that, six months from now, when someone asks how your trip was, you want to say, hey we had this really cool, great, (insert adjectives here) dinner and drinks for GF's b-day?

      14 Replies
      1. re: jbontario

        Either is fine. I want a memorable dinner for her with some good food.

        1. re: Matronix

          There are various ways a dinner can be memorable, and obviously one way is sharing your special meal with that special person. Great food is often memorable, all by itself. The first five places I mentioned above were all memorable for other reasons in addition to delicious, terrific food. If I had to pick two of those for "most memorable", they would be Alinea and North Pond.

          Alinea is really a "once in a lifetime food experience", with the presentation techniques as fun and entertaining as the food itself. To get an idea what this is like, there was a cartoon written about dinner at Alinea a few years ago; the dishes and techniques have changed since then, but it will still give you an idea of their "fun with food" concept: When I ate there again a few months ago, my dining companions all called it the best meal of their lives, and said it really opened their eyes with a truly unusual, entertaining experience.

          Last week, I happened to eat at three different Michelin one-star restaurants, but of these, North Pond is the dinner I will remember for a long time. First, of course, is its location in the middle of the park. Even as a longtime Chicagoan who has previously dined there, I still love walking through the greenery of the park, and happening upon this little building housing the restaurant, then looking out from dinner upon the pond and the skyline. On top of that, though, my dinner was just amazingly wonderful. There were specific dishes that wowed, including a warm vichyssoise (!) and a short rib topped with an incredibly concentrated red wine reduction. And Chef Sherman's style is to plate the various ingredients separately on the plate, so each dish is, in a way, its own little tasting menu, allowing you to eat from many separate tastes on the same plate. In my dinners I've loved pretty much all of those tastes. The desserts were some of the very best I've had in years, accomplishing the rare feat of combining unusual ingredients and presentations with amazing deliciousness.

          I also have fond memories of the other three places, particularly Grace for its subtle but perfect service and spaciousness, Everest for its view as well as memorably impressive service, and Naha for approaching the experience of a restaurant costing 2-3 times as much. But if I were choosing a place based on how memorable it is likely to be, that place would be Alinea (if you don't mind spending the money, of course) or North Pond.

          I'll add, though, that you can easily have a memorable dinner at a casual, moderately-priced restaurant as well. For example, above I mentioned Anteprima, a casual Italian neighborhood bistro on the North Side. Every time I go there, the food is outstanding, and I walk out the door wanting to return again soon. And I do, much more frequently than any other restaurant (even though it's not in my neighborhood). Granted, part of that is a matter of its affordability, but part of it is also knowing how consistently and reliably outstanding the food is there.


          1. re: Matronix

            I just ask because in our great city there are so many progressive evenings on which you could embark. I have eaten at Alinea once and (as I posted recently elsewhere) it was great but if I was coming to visit Chicago and have an "Evening" I wouldn't spent three to four hours sitting at a table . . . . Do you or your GF have any specific interests in Food & Wine -- farm to table, craft beer/cocktails paired with food, great ingredients in more casual settings? By all means I am not pushing you away from a fine-dining wear a jacket experience if that is what makes your apres-dinner plans . . . the most fun, just suggesting that for a birthday there are so many fun things to eat, drink and do.

            1. re: jbontario

              I'm not pushing for a jacket wearing experience, so something more casual would be great. We love craft cocktails as we can get them here at many places and love trying them. We are looking for a good meal and drinks. If that helps.

              1. re: Matronix

                It all comes down to what you consider a "special dinner". For craft cocktails and terrific food, Sable is a great choice, and so is GT Fish & Oyster. Both are lively, fun places, and Sable in particular has some of the best cocktails in the city. (For food, don't miss Sable's sweet corn crème brulee, a savory version of the classic dessert.) North Pond and Naha are more upscale and elegant, but neither requires or recommends jackets. Alinea, Grace, and Everest are still more upscale and elegant, and do require/recommend jackets. So it just depends on what kind of experience you're looking for.

                One possibility, if your visit here includes more than one dinner, is to do one dinner at one of the upscale places (with or without jackets), and another at one of the fun places (Sable, GT Fish). Another possibility is to do one or more of these for lunch or brunch; GT Fish and Naha are open for lunch on weekdays, Sable and GT Fish for brunch on Saturdays/Sundays, and North Pond for brunch on Sundays (when daylight makes it a great time to experience its lovely setting in the park).

                Don't worry too much; there's no "right" or "wrong" answer here. Chicago has lots of places to eat, and it's just a matter of picking one(s) you think you'll enjoy the most, for your particular occasion and preferences.

                1. re: nsxtasy

                  I was actually just looking at the menus of Naha and North Pond and both of those look great. And by special diner... with her, she is easy to please.. I guess I just meant something not-norm or average. We come from the Twin Cities and have lots of good food here, so something of that caliber. I think the places you have been listing are in the correct realm, so thank you. Now to narrow it down. I like you suggestions for breakfast/lunch/brunch as well. We are leaving out late afternoon on Monday so catching a lunch at a place is also possible. I will take a look at Sable and GT as well.. we do love a good cocktail. Also, since you seem to be well informed.... are there any great, solely, cocktail bars that are a must visit?

                  1. re: nsxtasy

                    Looked over Sable and GT just now. Both look like solid Suggestions. I think I am actually trying to narrow it down between Naha and Sable. Sable almost seems like a more of a get a great bite to eat, enjoy yourself type of meal... That is what we like to do. (I would pick GT in a heartbeat but she doesn't love seafood as much as I do.)

                    1. re: Matronix

                      Yes, that's correct. Sable is terrific - a casual place with an open kitchen where you can watch them prepare the food. The bar itself (the other side of the hoststand/entrance) is one of the best places for craft cocktails, and a lot of folks go there just for drinks. But the food is absolutely top notch. I love the fact that you can order half portions, so you can try a lot of different things. Naha is terrific in its own way, but it is a very different place to eat, very upscale and elegant, rather than brash and trendy like Sable. In MSP terms, Naha is comparable to La Belle Vie (which I liked very much).

                      >> I like you suggestions for breakfast/lunch/brunch as well. We are leaving out late afternoon on Monday so catching a lunch at a place is also possible.

                      Great! Just be aware that our breakfast/brunch specialty places (including Jam, perhaps our best) don't accept reservations, and waits to be seated on Sundays between 9:30 and 1:00 can be lengthy (30-60 minutes). So for Sunday brunch you might want to consider a place that accepts reservations (such as North Pond). Weekdays, our breakfast/brunch places have no waits at all, so maybe Monday will be a good day for breakfast at Jam. (Or lunch at Naha.) Also note that Jam is open till 3 pm and is on the way to O'Hare (right next to the Logan Square el stop), so if you're flying home from O'Hare, it may be convenient to go on your way to the airport. It's also on the way if you're driving home from downtown Chicago.

                      Another word about Jam, because it's rather unique. (It's not like Hell's Kitchen in Minneapolis, for example, which is great for breakfast but also unique.) The chef-owner of Jam, Jeff Mauro, has a fine-dining background, and wanted to create a casual, inexpensive, fun breakfast-focused restaurant but with food that's way more creative (and delicious) than most. Just a great place.

                      >> are there any great, solely, cocktail bars that are a must visit?

                      Eater's "cocktail heat map" is a pretty good guide:

                      1. re: nsxtasy

                        Alright, made a reservation for Sable because I think she will enjoy that the most. Really tough choice though between it and Naha.

                        I will look into Jam for sure though... we love some breakfast/brunch... so any recommendations for that would be great. We are staying over near Mill. Park.

                        1. re: Matronix

                          For our more unusual breakfast specialty restaurants, you'll have to travel at least a little bit. Jam, for example, is five miles northwest of the Loop, where Millennium Park is. About a mile south of Millennium Park, at Roosevelt (12th) and Wabash, is Bongo Room, which specializes in creative pancakes with sauce, such as pretzel pancakes with white chocolate caramel sauce. Their standard portion size is three gigantic pancakes; you can also order one-third and two-thirds portion sizes, which lets you try more than one dish. Another of our very best breakfast places is/are M. Henrietta and M. Henry, way up on the north side; M. Henrietta is at the Granville el stop, but I'm guessing perhaps that's a bit far to travel. Those three are perhaps our most unusual.

                          Breakfast specialty places fairly close to Millennium Park include Eggy's Diner in Lakeshore East, and Yolk on Ohio east of Michigan. Yolk also has a location a mile south, near Bongo Room. Lou Mitchell's is just west of the Loop. These places are not as creative/unusual as the previous group, but they are geographically more convenient.

                          Some other options in/near the Loop are not exactly breakfast specialty restaurants, but are worth considering: Toni Patisserie for French pastry and breads, Intelligentsia for coffee (locations on Randolph and on Jackson), and Do-Rite Donuts, Firecakes, and Glazed and Infused (location on Hubbard) for donuts. These last two are just across the river, north of the Loop. Do-Rite serves Dark Matter coffee also.


                          1. re: nsxtasy

                            Wanted to give you an update. We are in Chicago right now (leave to go back home on Monday.) We have eaten at Sable, Bang Bang Pies, GT Oyster, and Brown Bag Seafood Company. All of them have just been fantastic. Thank you for the recommendations of Sable and GT. We enjoyed the drinks and most of the food at Sable. There was one item we didn't like and they just took it back and didn't charge us for it which was great. We went to GT for Brunch on Saturday and that was just fantastic. I blame you for me finding a new tea I like and now have to order from Rare Tea Cellar. :) We might go back to Bang Bang and Brown Bag on Monday as they are quick to eat and we don't have that much time in the day. Only thing else we have is to try and find somewhere for dinner tonight. (Sunday) ... If you see this and have any suggestions let me know. Something simple but delicious.

                            1. re: Matronix

                              >> Only thing else we have is to try and find somewhere for dinner tonight. (Sunday) ... If you see this and have any suggestions let me know. Something simple but delicious.

                              I'm looking at Opentable and here are a few places I recommend, depending on what kind of food you prefer; all are casual and delicious:

                              Mexique, for contemporary Mexican food in a bistro setting - 2 miles from downtown - tables for 2 available tonight at 6:00 and 8:30 but not in between - (another option for contemporary Mexican is Salpicon, which is closer, in Old Town - )

                              Anteprima, for Italian food in a bistro setting - 7 miles from downtown - availability is wide open - (another good option for Italian is Piccolo Sogno Due, which is in River North - )

                              Quartino, for Italian in a small plates format - in River North - availability is wide open -

                              Mercat a la Planxa, for tapas - in the Loop - availability is wide open - (another tapas option is Café Iberico but they don't accept reservations - )

                              If I were choosing based solely on the most delicious food, Mexique and Anteprima would be my top two picks, but neither is right downtown.

                              1. re: nsxtasy

                                Thanks once again for the suggestions. I feel like I owe you a cocktail or meal next time I am in town. :) Last night we ended up going to Mercat. Last Novemenber we went to Spain on vacation so the Mercat menu spoke to us. It was a great meal and a great way to end the night.

                                Thanks so much for sharing your good food knowledge.

                              2. re: Matronix

                                Glad you've been having a good time. I love Bang Bang.
                                Given your criteria of "simple and delicious" and your enjoyment of cocktails, I would recommend Bandera, mainly for its convenient location. Part of a mini-chain, but the food is well-executed, and there is nice music and a nice view. One of those places where tables are almost always available, so reservations are not a worry.

            2. Restaurant taste is such a personal thing. Many restaurants listed by others are highly regarded and highly rated by professional critics. I personally would never turned down a free (for me) invitation to Alinea but I get the feeling that the bloom has gone off the rose so to speak and adopted a wait and see attitude about going when my SO suggested it for a special occasion. Of the finest of the fine dining spots Grace is number one on my wish list. Off my wish list is Sixteen because, for the expense, I found it all show and little substance and really only enjoyed a handful of the dishes. We were treating another couple for dinner and none of us walked away with any thoughts of returning. If you are spending upwards of $250 for dinner you have a right to expect a lot. Sixteen was 4 thumbs down with my SO, who treated, silently thinking "way down!"

              I have tried for years to like North Pond, if only for its gorgeous setting in Lincoln Park, but it has never delivered for me. It is among some very experienced and informed critics favorite restaurants but I always leave feeling like "we ate here again, WHY?"

              Naha has great luxurious food in a great setting that never seems crowded and is easy to converse in, sometimes in the middle of the week though the place is literally a dead zone with only two or three tables also occupied. it can make you want to whisper rather than talk. On the other end of the conversation spectrum is the relatively new Davanti Enoteca. I really enjoyed the food but unless you sit at the bar conversation is not comfortably possible.

              Boka under it's new chef is hit and miss for me but I have only been twice. The first time our appetizers were excellent. My SO ordered the odd sounding rye pasta with carroway and chestnut and he was practically licking his plate. I ordered the always reliable (from the Chef's tenure at the Lobby) ricotta gnocchi/gnudi and it was delicious. My main was the scallops which were good but not something I need to order again. The SO went for the Roasted Chicken from The Lobby days, now available for one, and he didn't like it at all finding it dry and its accompaniments lack luster. This from a guy who ordered it every single time we ate at the Lobby!
              Second visit came after a partial evolution to the spring menu. It should be noted that the menu here is extremely limited but the rye pasta was off the menu and I wanted a different starter than gnocchi. I don't remember exactly what I had on a blustery cold April night except it had fava beans, fiddlehead ferns and some grilled squid or octopus. The protein was good but nothing else complimented it or screamed "freshness and spring". It was as if the spring ingredients were an afterthought and I couldn't identify what the saucing was except to say it was bland and flavorless. My duck main also resided in the uninspired camp. SO was lucky with his gnocchi and not unhappy with his grilled short ribs. In sum we wont be running back but wont be running away.
              Very anxious to try Elizabeth and Goosefoot but the BYOB at Goosefoot and Elizabeth's unconventional dining experience mean I will have to convince some friends to go with out my SO..

              Good Luck!

              13 Replies
              1. re: KateBChi

                >> If you are spending upwards of $250 for dinner you have a right to expect a lot.

                I agree. Especially if that $250 figure is per person, which it is at Alinea, Grace, Everest, and Sixteen, I think you ought to expect extremely delicious food - maybe not every single dish, but most of the dishes should make you want to shout "WOW, this is DELICIOUS!". And flawless service. In my experiences, Alinea, Grace, and Everest accomplish this extremely well, as do North Pond and Naha (despite their lower price point). Other places (including Sixteen), not as much.

                >> Very anxious to try Elizabeth and Goosefoot but the BYOB at Goosefoot and Elizabeth's unconventional dining experience mean I will have to convince some friends to go with out my SO.

                I'm not sure why either place would be avoided, although neither would be my first choice for a special dinner either.

                Elizabeth, which is one of the three places I went last week, really didn't strike me as an unconventional dining experience, aside from the need to pay for the reservation in advance. One formerly unconventional aspect, the communal tables, has been discontinued; we sat at our own table for two. Granted, they serve from a fixed tasting menu, but that's not so unconventional these days. It actually seemed pretty conventional to me. One difference from the places I recommended previously is that the food was generally very good, but not consistently exceptional; some dishes (notably the sunchoke soup) were outstanding, while others were just okay, and the ribeye was a clear miss, arriving mostly raw. I enjoyed Elizabeth - it's worth trying - but it wasn't so great that I'm looking forward to returning.

                It's been over a year since I went to Goosefoot, and I thought it was very good. The food was a bit more uniform than Elizabeth, with pretty much all the dishes qualifying as very good, although without any particular standouts but no clear misses either. Like Elizabeth, I enjoyed it and it's worth trying, but it wasn't so great that I'm dying to go back. And I'm not sure why the BYOB aspect would make anyone want to avoid it.

                1. re: nsxtasy

                  As for Goosefoot the BYOB is actually a plus for me as I like bringing my own wine on some occasions but no liquor license is a serious negative for an SO who likes his pre dinner cocktail. I didn't know Elizabeth discontinued the communal seating. That was the only off-putting element for me.

                  1. re: nsxtasy

                    BYOB may also be a negative for out-of-town visitors arriving by plane, as they would need to either (a) bring the wine as checked luggage, or (b) buy wine when they arrive. From my perspective, the appeal of BYOB at a high-end restaurant is the ability to enjoy a special bottle(s) from our home cellar with a superlative meal.

                    1. re: masha

                      Thanks to both of you for the explanation. Both stated downsides of BYO make sense. (And of course there are upsides, the cost factor also worth mentioning.)

                      1. re: masha

                        I was actually thinking about this. This would be a downside for me. I don't want to have to go find a bottle when I get to town for dinner.

                        1. re: Matronix

                          Understood entirely. The cost-savings on BYOB are also diminished if you want to buy a "special" wine just before the dinner, as you pay a mark-up for a bottle that has already aged. Still less expensive, typically, then the mark-up that the restaurant charges, but expensive compared to a bottle that was purchased young and held for several years.

                    2. re: KateBChi

                      I guess as one person stated, I guess I am not looking for the "Have to wear a jacket" experience... more of a good meal and even cocktails type of experience.

                      1. re: Matronix

                        I have spent a lot of time in the Twin Cities and have enjoyed the range from Bar Lagrassa (one of my favorite restaurants around), Manny's (the spinach salad is the best medium to serve for bacon in the city), pizza at La Luce and many others.

                        I really like Naha and you'll have a great meal, its not festive though. I agree with nsxtasy on the food at North Pond, but i don't find the setting to be all the exciting. I personally prefer a vibrant atmosphere that our finer dining doesn't' offer. Sable is also nice, but it's become a bit touristy and even seems a bit like the 5-year ago great new place that has begun to age.

                        For something more casual and fun (as I would call it) I recommended this itinerary that was a really fun night out in Chicago. Start with well crafted cocktails and light bites at The Dawson (i enjoyed sitting at bar upstairs with a couple friends and having whiskey cocktails and a bunch of the apps/small plates). For your second (and maybe 3rd) stop, walk across the street for some good old-school Chicago and grab a drink or two at Emmitt's or Richard's Pubs. After a drink or two, walk down Halsted St 5 mins to W Randolph and put your name in at Au Cheval. While you're waiting for table at Au Cheval for the best pork chop and cheeseburger (in my book that I've ever had) walk a few doors down to Lone Wolf or Little Goat and have another cocktail or two. LG has a rooftop deck if its nice outside. All of this in jeans and with nice weather in May would be a nice night out.

                        1. re: jbontario

                          Bar La Grassa is one of my favorite places. That is where we went for her birthday last year. This year, The Strip Club Meat and Fish, will be the destination for her birthday dinner.

                          Lots of great suggestions. The Dawson looks great... we love drinks and small plates. That one is tempting to try as well.

                          1. re: Matronix

                            >>>This year, The Strip Club Meat and Fish, will be the destination for her birthday dinner.<<<

                            I am confused. You said you were bringing your girlfriend to Chicago for her birthday dinner and The Strip Club, if I recall correctly, is in St. Paul, Minnesota.

                            1. re: Fowler

                              Perhaps there will be multiple celebrations, with some of them around but not on her birthday.

                              1. re: Fowler

                                nsxtasy is correct. The Strip Club is on her actual birthday since it is during the week. Going there with friends... normal thing for at least one or two birthdays are year. Her and I are venturing to Chicago for another celebration. Actualy the Chicago trip is a complete surprise for her. She doesn't even know it is planned, she just knows we are going away for the weekend.

                                1. re: Matronix

                                  You are one lucky man. I wish my wife would let me take her to a strip club for her birthday.

                      2. That is a tough question to answer because Chicago is such a fantastic world-class food city.

                        I can pretty much guarantee you that you and your girlfriend would not forget a dinner at Alinea. My favorite restaurant in the USA is French Laundry and I think Alinea may be in my top five.

                        Everest is also very good and something memorable. Their wine list is quite pricey but you said price is "open" so that should perhaps be a place to consider. All of the times I have been there the food and service were excellent.

                        My friends and I have had very good luck with Grace as well. Their duck and sweetbreads are particular standouts.

                        Have fun and enjoy your visit!