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Memorable dinner for one near Trump Hotel?

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I'll be in Chicago this Monday evening on business, staying at the Trump Hotel. This will be my first trip away after my wife and I had a baby three months ago--so while I will miss them, I am ready to treat myself to an excellent meal :) Any suggestions for a "treat yourself" meal where I won't look strange dining alone? I am open to all cuisines but would prefer it be walkable from the Trump Hotel. I am willing to spend up to $150 but could go over that if it is truly merited. Is it worth seeing if I can get Alinea tickets? What about Topolobampo and Sixteen (at the Trump)? So many options, so little time... thank you!

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  1. Alinea is a no-brainer but they are not open Mondays if that's the only night you're in town.

    I stay in that area when visiting Chicago and have always enjoyed my meals at Tanta as well as Avec.

    1 Reply
    1. re: ipsedixit

      Alinea is fantastic and as great as ever - I went back a couple of months ago (not my first time) and it was one of the top three meals of my life - but it will well exceed the price point stated.

    2. Alinea would be more than double your price point and IMHO is past her prime. Anyways Alinea, Topolobampo and many of Chicago's top venues such as Grace and Moto are closed on Mondays.

      Sixteen (the Michelin two star venue in your hotel) is open; their menu changes completely with the seasons so their new spring menu likely will have just rolled out - though this too will be well over your price point unless you stick with water. It can be a fantastic experience though when they are firing on all cylinders.

      Open on Mondays, a short walk from you and in your price point would be GT Fish & Oyster; a great choice if you are into seafood. A short cab ride from you are Boka (contemporary American), Balena (Italian), Publican (nose-to-tail) and Embeya (Asian). All of these are excellent and viable as a solo diner. I recommend checking out their websites and seeing which seems most appealing to you.

      1. If you want a meal that is a true splurge, some of the best food in the entire city, while still keeping it within your $150 target limit, I recommend Naha. James Beard Award-winning chef-owner Carrie Nahabedian is turning out terrific food, yet it doesn't cost as much as some of the other top tables in town (for example, TRU and Sixteen will exceed your limit substantially, as will Alinea). And they will pamper you as a solo diner. From the Trump Hotel, the six-block walk should take less than ten minutes. www.naha-chicago.com

        I love GT Fish & Oyster, which is mentioned by Gonzo, but it's a quite casual restaurant, serving seafood small plates, and it sounds like you're looking for more of a splurge than that. If not, then also worth a try in the casual category is Sable, which also follows the small plates format and has terrific contemporary American cuisine. Both of these are chef-driven restaurants with mixologists creating craft cocktails. For Italian food, Piccolo Sogno Due is excellent. Sable and Piccolo Sogno Due are both three blocks from the hotel, while GT Fish is eight blocks away. All of these are open for lunch as well as dinner. www.piccolosognodue.com www.sablechicago.com and www.gtoyster.com

        There are so many great restaurants within a few blocks of the Trump Hotel that there's no real need to take a cab to restaurants more distant than these.

        3 Replies
        1. re: nsxtasy

          I too am off to Chicago and am looking for some nice solo meals. Frequently when eating alone I find eating at the bar more comfortable than at a table--lest sense of reducing the waitstaff's tips.

          Any restaurants in Chicago to recommend for meals at the bar with or without reservations?

          (I have been checking out some of the suggestions in your post and the menu at Sable looks really interesting so I am going there for sure)

          1. re: estyle

            Places in Chicago I am aware of with excellent food, lively atmosphere and bar seating where you can order off of the regular menu include:

            *GT Fish & Oyster in River North (Seafood)
            *Frontera Grill in River North (Regional Mexican). You can also order off of Topolombampo's menu at the Frontera Grill bar
            *Bavette's Bar & Bouef in River North (Steakhouse)
            *La Sirena Clandestina in West Loop (Spanish)
            *Girl & the Goat in West Loop (Nose-to-Tail)
            *Little Goat Diner in West Loop (American Diner)
            *Embeya in West Loop (Modern Asian Fusion)
            *Balena in Lincoln Park (Italian)
            *Boka in Lincoln Park (Contemporary American)

            I am not sure if you can specifically reserve seating at the bar, but at most of these (especially on weeknights) it is not too hard to score bar seating as a single (Girl & the Goat and Frontera Grill would be most difficult, but still quite feasible if you are OK with possibly having a short wait).

            1. re: Gonzo70

              Thank you! I am filling out my dinners for the rest of the trip and this is a great list. I am really looking forward to the food portion of this trip.

        2. Agree with a lot of people here. Places I've been relatively recently and like. Boka, GT Oyster (not formal but the food is good if you want to "treat yourself" order the seafood tower), and Sable. We've been to Naha 10+ (?) times and our last was less than what it has been in both food and service. I wonder if anyone else has had this problem? That said, all the other experiences have been good. I wouldn't hesitate to go back or recommend the place.

          1 Reply
          1. re: HoosierFoodie

            I hesitate to say anything negative about Naha because the food is always great quality and well prepared. I've been going off and on since it opened but for some reason it was never a place I went with my SO until recently. He loved it the first two visits (he did order the best food between us) but by the third recent visit a bit of restaurant fatigue had set in for me. I initially chose it because I needed something between the loop and cabbable from my home and a place that wouldn't be slammed, rushed or hard to converse in. It definitely fits that bill but the food, while luxurious, wasn't terribly interesting. I would never knock the place or skip a dinner there but when the "lets meet between my office and home" idea comes up I try to spread the love around a bit. Service on the other hand has never lagged for me but sometimes we are only one of a few tables eating so it's hard to overlook us.