Dining alone in Chicago--Loop/Downtown area suggestions?
I'm going to be in Chicago for a few nights next week and will be probably dining alone for dinner...I ususally resort to sitting at a sushi bar when this happens (luckily not so frequently--I don't really like eating alone!), but am hoping to break out of that mold. Is there anyplace with great food and ambience, not stuffy, in close proximity or centered in the heart of Chicago? NOTE: I am not into steakhouses at all, or anything that would scream out at you 'dining haunt for buisness-types on expense accounts'.
A fun place with EXCELLENT cocktails is NoMi just north of Chicago (800N) on Michigan.
It has a chic ambience and a fun lounge area where you can enjoy cocktails, wine, and/or dinner at the bar, in the lounge or one of the beautiful wine tasting tables right off of the wine cellar.
I would recommend a small sushi platter with a glass of champagne, or the sliders with a Negroni at the bar.
Another fun place is the bar at Rick Bayless' Frontera Grill. Modern and savory Mexican, I would recommend a margarita, straight up, with your choice from the Ceviche bar alongside the Tamales de puerco. Just north of the river on clark (around 400N.)
Late night food if you catch yourself out, the Wiener's Circle.
Open till 4am, you get the char polish (or all beef red hot) with everything on it, grilled onions. Don't fear yellin your order out ahead of people. The les demoiselles d'avignon will give you a hard time if they smell fear on you.
Bring someone with you if you get the fries. 2600 N. clark.
Note that at NoMI in the afternoon, particularly on weekends, you will find boatloads of tourists in Disney Store sweatshirts. Mostly parents stunned and in need of sustenance after taking in American Girl Place with their daughters (and possibly the daughters, totally absorbed in their new dolls)
I occasionally dine alone. I am not reluctant to go ANYWHERE to dine alone. Any good restaurant should make you feel totally at home in doing so. You can sit at the bar or at a table - sit where YOU want to sit - and they should be extremely accommodating, either way. So I would recommend that you feel free to go anywhere you like, for whatever cuisine you like.
There are two places I have dined in/near downtown Chicago where the service stands out as extraordinary. One is the Lobby Restaurant in the Peninsula Hotel. That's the name of the restaurant, and should not be confused with Avenues, which is also in the Peninsula. The setting is beautiful, with high ceilings and floor-to-ceiling windows along one wall. The food is outstanding, and later on Friday and Saturday nights, they offer the all-you-can-eat chocolate dessert buffet. I have eaten there alone, and their staff was extremely accommodating and welcoming, showing me to a desirable table (not one stuck off in the corner!), asking me if they could bring me a newspaper, etc.
The other is Everest. While I have only eaten there with others, I have seen how sensitively (and friendly) their service has been with children, and I can only imagine that they can do the same with solo diners. The service is excellent (but if you define "stuffy" as jacket and tie, well, that's what men wear there). Everest is one of the best restaurants in the city (THE best, IMHO), with incredible food and a delightful view (from the top of the Chicago Stock Exchange building) to go along with the impeccable service.
The Peninsula Chicago
108 East Superior Street (at North Michigan Avenue)
Chicago, Illinois 60611, USA
440 S. LaSalle St., 40th Floor
Chicago, IL 60605
I am not sure from your comment about "anything that would scream out at you 'dining haunt for business-types on expense accounts'" whether you are referring to price (high price alone?), or value (high price for mediocre cuisine?), or atmosphere (loud obnoxious types who don't appreciate food?), etc. FWIW, the prices at Everest (entrees $32-46) are consistent with its reputation as among the best in the city, although it is less expensive than some others in this group, such as Alinea, Tru, and Charlie Trotter's. The prices at the Lobby are lower, with entrees in the $15-30 range, as I recall. (The weekend "Chocolate Bar" is $30.) If you are looking for more moderately priced restaurants in the downtown area, check out this topic (for its dinner suggestions, not its lunch suggestions): http://www.chowhound.com/topics/360453
Where exactly will you be in Chicago? That could help with suggestions. Will you have time (or the inclination) to take the train to some neighborhoods (15-30 mins tops away from downtown)? A lot of our neighborhoods have good places to eat for single dinners that are unique to the city.
That being said, Avec and Blackbird have been mentioned on this board for excellent solo dining. You may want to do a search on those two names (and I see that Amata just wrote in Avec)
The Big Downtown at the Palmer House is tasty. They have a lobster ravioli that is excellent. And GREAT dirty martinis!
Bistro 110 (next to Ghiradelli'/near the Water Tower) is wonderful. One of my favorite places in Chicago. It's a bit touristy being that it is right of the M Mile, but the roasted garlic and bread is to die for.
The Atwood Cafe (a couple of blocks from the Chicago Theater on State Street) is very good, but can get crowded around theater times. It's very popular with the theater crowd.